A Summertime Favorite: Penny Loafers
Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.
The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 
If you haven’t yet got yourself a pair, consider some of these:
Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.
(Pictured above: Hooman Majd in his fifteen year old Edward Greens)

A Summertime Favorite: Penny Loafers

Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.

The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 

If you haven’t yet got yourself a pair, consider some of these:

  • Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
  • Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
  • A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
  • Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.

(Pictured above: Hooman Majd in his fifteen year old Edward Greens)


coppingandscheming asked:


Hi, I’m a big fan of the Clark desert boot. However i think it’s time to upgrade. I would like to find an option that is one step up in terms of quality and price. Do you have any suggestions?

Ah, the desert boot. The shoe that launched a thousand menswear blogs. One step up from Clarks unassailably basic desert boot (best in sand suede) is sort of a no man’s land of footwear. Clarks boots retail at $120 (although currently on sale <$100 at Need Supply). As you shop up the price ladder, styles vary a little, but quality doesn’t too much, until you get into the welted footwear makers; of course, their prices are triple the price of a pair of Clarks, or more. Some options:
A choice so obvious it risks being taken for granted is J. Crew’s Macalister boot. Macalisters are a little sharper and shapelier than Clarks and made in Italy of decent if not superlative soft suede. In the range between Clarks and $200, I’d pick the Macalisters. Plus they’re on sale for about $100 through May 24 with code PACKME.
Loake makes a desert boot that runs about $150. Loake is a Northampton-based shoe brand but their desert boots are made outside the UK in the EU. A little more interesting than the Clarks, but in my opinion, part of Clark’s appeal is their knockaround, anonymous quality. I’m borderline allergic to Loake’s darker color versions with contrast stitching.
If you’re willing and able to spend more or wait for sales, two upgraded desert boots worth buying are Church’s Sahara (pictured above) or the Alden unlined chukka, which is more often sold with a leather sole rather than traditional desert boot crepe.
The Church’s version drains any vintage milsurp vibe from the desert boot—Sahara are more narrowly lasted with Goodyear welting with much finer stitching that the Clarks boots. If you’re into desert boots for their mod connotations, I think the Church’s shoes fit the narrow-trousered aesthetic better than current Clarks. Note that if you have large feet, the slightly longer last and higher lacing may exaggerate that effect.
The Aldens are considered by many the perfect casual shoe. Neither too sharp nor too clunky, they’re quite comfortable and go as perfectly with denim as a good leather jacket and a plain tshirt. They’re also distinctive looking, with a double line of stitching on the  quarters, which are much less sharply angled than most chukkas/desert boots. The only drawback for me is the cost—about $500 and rarely discounted.  Ebay or other secondary markets are better bets for off price Aldens.
-Pete

Hi, I’m a big fan of the Clark desert boot. However i think it’s time to upgrade. I would like to find an option that is one step up in terms of quality and price. Do you have any suggestions?

Ah, the desert boot. The shoe that launched a thousand menswear blogs. One step up from Clarks unassailably basic desert boot (best in sand suede) is sort of a no man’s land of footwear. Clarks boots retail at $120 (although currently on sale <$100 at Need Supply). As you shop up the price ladder, styles vary a little, but quality doesn’t too much, until you get into the welted footwear makers; of course, their prices are triple the price of a pair of Clarks, or more. Some options:

  • A choice so obvious it risks being taken for granted is J. Crew’s Macalister boot. Macalisters are a little sharper and shapelier than Clarks and made in Italy of decent if not superlative soft suede. In the range between Clarks and $200, I’d pick the Macalisters. Plus they’re on sale for about $100 through May 24 with code PACKME.
  • Loake makes a desert boot that runs about $150. Loake is a Northampton-based shoe brand but their desert boots are made outside the UK in the EU. A little more interesting than the Clarks, but in my opinion, part of Clark’s appeal is their knockaround, anonymous quality. I’m borderline allergic to Loake’s darker color versions with contrast stitching.

If you’re willing and able to spend more or wait for sales, two upgraded desert boots worth buying are Church’s Sahara (pictured above) or the Alden unlined chukka, which is more often sold with a leather sole rather than traditional desert boot crepe.

  • The Church’s version drains any vintage milsurp vibe from the desert boot—Sahara are more narrowly lasted with Goodyear welting with much finer stitching that the Clarks boots. If you’re into desert boots for their mod connotations, I think the Church’s shoes fit the narrow-trousered aesthetic better than current Clarks. Note that if you have large feet, the slightly longer last and higher lacing may exaggerate that effect.
  • The Aldens are considered by many the perfect casual shoe. Neither too sharp nor too clunky, they’re quite comfortable and go as perfectly with denim as a good leather jacket and a plain tshirt. They’re also distinctive looking, with a double line of stitching on the  quarters, which are much less sharply angled than most chukkas/desert boots. The only drawback for me is the cost—about $500 and rarely discounted.  Ebay or other secondary markets are better bets for off price Aldens.

-Pete

How Much Should You Spend on Dress Shoes?
One of the questions I frequently get in my inbox is: “I’m looking to buy a better pair of dress shoes, and only have X to spend. Should I save up for something better, or is so-and-so brand OK?” Like with many questions we get, a lot depends on the person asking.  
It’s worth noting, however, that in footwear (like in everything), there are serious diminishing returns after a certain point. Very roughly speaking, that point tends to be around $350 at full retail, although what’s sold at full retail can be had for less with smart shopping (eBay, factory seconds, seasonal sales, thrift stores, etc).
The Unfortunate Reality of Diminishing Returns
There are a number of things that go into the construction of a good shoe, but the two biggest are: the quality of the leather used and how the soles have been attached. Jesse did a great job in describing the difference between corrected grain and full grain leathers here. It’s also worth noting that even among full-grain leathers, there can be differences in quality. Additionally, most well made shoes will have their shoes attached through a Goodyear or Blake stitching process. Jesse reviewed some of these in the second episode of our video series, and you can read more about each technique here. The short of it is: with a sole that’s been stitched on, rather than glued, you can more easily resole your shoes, which means you don’t have to bin them when the bottoms wear out.
In the past, the “entry price” for good (dress) shoes tended to be around $350. These were usually from Allen Edmonds, Ralph Lauren, and Brooks Brothers, although not everything from these brands were worth buying. There were also some European names such as Herring and Loake’s 1880 line.
After this, you get marginally better constructions, but the differences become smaller and smaller (perhaps a leather insole vs. a fiberboard insole, or a sole that&#8217;s been attached by hand rather than machine, or slightly better leathers used for the uppers). Largely, as you move up from the $350 MSRP mark, you’re paying for design. A $1,250 pair of Edward Greens won’t last you 4x longer than a $350 pair from Allen Edmonds, but to many, they’re shaped and finished more handsomely.
The Emergence of a More Competitive Market
The good news is that the market has gotten a lot more competitive in the last five years, and the cost/ benefit curve has smoothed out considerably. Today, there are companies such as Beckett Simonon, John Doe, and Jack Erwin below the $200 price mark (the last of which I was particularly impressed by). Just a hair over $200 is Meermin, which I still think is one of the best values for (relatively) affordable footwear. They have a “Classic” line for about $200 (but with customs and duties, you might pay around $230) and a higher end “Linea Maestro” line for about $300 starting. And at the $350 mark, there’s more than Allen Edmonds and Loake’s 1880 these days. Paul Evans, Kent Wang, and Howard Yount are all good companies to look into.
The question of how much should you spend isn’t about what’s “good” in the footwear market, it’s about what’s “good enough” for you. For dress shoes, the only real criteria are: quality full-grain leather uppers and some kind of stitched on sole. Much of the rest is about aesthetics and personal preference.
(Photo: Crockett &amp; Jones&#8217; Whitehall oxfords at Ben Silver)

How Much Should You Spend on Dress Shoes?

One of the questions I frequently get in my inbox is: “I’m looking to buy a better pair of dress shoes, and only have X to spend. Should I save up for something better, or is so-and-so brand OK?” Like with many questions we get, a lot depends on the person asking. 

It’s worth noting, however, that in footwear (like in everything), there are serious diminishing returns after a certain point. Very roughly speaking, that point tends to be around $350 at full retail, although what’s sold at full retail can be had for less with smart shopping (eBay, factory seconds, seasonal sales, thrift stores, etc).

The Unfortunate Reality of Diminishing Returns

There are a number of things that go into the construction of a good shoe, but the two biggest are: the quality of the leather used and how the soles have been attached. Jesse did a great job in describing the difference between corrected grain and full grain leathers here. It’s also worth noting that even among full-grain leathers, there can be differences in quality. Additionally, most well made shoes will have their shoes attached through a Goodyear or Blake stitching process. Jesse reviewed some of these in the second episode of our video series, and you can read more about each technique here. The short of it is: with a sole that’s been stitched on, rather than glued, you can more easily resole your shoes, which means you don’t have to bin them when the bottoms wear out.

In the past, the “entry price” for good (dress) shoes tended to be around $350. These were usually from Allen Edmonds, Ralph Lauren, and Brooks Brothers, although not everything from these brands were worth buying. There were also some European names such as Herring and Loake’s 1880 line.

After this, you get marginally better constructions, but the differences become smaller and smaller (perhaps a leather insole vs. a fiberboard insole, or a sole that’s been attached by hand rather than machine, or slightly better leathers used for the uppers). Largely, as you move up from the $350 MSRP mark, you’re paying for design. A $1,250 pair of Edward Greens won’t last you 4x longer than a $350 pair from Allen Edmonds, but to many, they’re shaped and finished more handsomely.

The Emergence of a More Competitive Market

The good news is that the market has gotten a lot more competitive in the last five years, and the cost/ benefit curve has smoothed out considerably. Today, there are companies such as Beckett Simonon, John Doe, and Jack Erwin below the $200 price mark (the last of which I was particularly impressed by). Just a hair over $200 is Meermin, which I still think is one of the best values for (relatively) affordable footwear. They have a “Classic” line for about $200 (but with customs and duties, you might pay around $230) and a higher end “Linea Maestro” line for about $300 starting. And at the $350 mark, there’s more than Allen Edmonds and Loake’s 1880 these days. Paul Evans, Kent Wang, and Howard Yount are all good companies to look into.

The question of how much should you spend isn’t about what’s “good” in the footwear market, it’s about what’s “good enough” for you. For dress shoes, the only real criteria are: quality full-grain leather uppers and some kind of stitched on sole. Much of the rest is about aesthetics and personal preference.

(Photo: Crockett & Jones’ Whitehall oxfords at Ben Silver)

Improvements at John Doe

John Doe recently loaned me a pair of their latest oxfords so I could check out the improvements they made since my last review. The shoes arrived last month, and they’re indeed much better. The new leathers are sourced from a different tannery, and feel much more supple and natural than their previous materials. The linings are also better attached, so there’s no more bubbling from an uneven application of glue. Additionally, the stitching is straighter, and without the punched brogue decorations, there are fewer places for something to go wrong. All in all, it seems they’ve upgraded their materials, tightened up their quality control, and are better at working with their factories.

I think readers will find there’s still a significant jump in quality as you go from these to brands such as Allen EdmondsLoake, and Meermin, but those will range anywhere from $200 to $350 at full retail. There are, of course, things such as Allen Edmonds’ factory seconds and the companies that Loake privately produces for (such as Charles Tyrwhitt), and those will sometimes go on sale, but none will match the very competitive price of John Doe at ~$150. For people with a hard budget of ~$150 or less, there are really only a few options.

The first, of course, is to go second hand, which you can get through thrift stores (using Jesse’s very useful thrifting guide) or our eBay roundups. I really like Ralph Lauren and Jesse likes Florsheim, but Allen Edmonds, Loake, and Brooks Brothers are also good names to search for. Just be discerning, as not all shoes from these companies are worth buying.

If you’re not comfortable with buying used shoes, then there’s suede, where you can “by-pass” the manufacturer’s need to cut back on quality materials. In comparison to “regular” leathers, the difference between low- and high-quality suede will be much smaller. Whereas corrected grain leathers can develop unsightly “cracks” over time, low-quality suede can stay pretty consistent if you know how to take care of it.

Outside of that, there are a number of shoe companies who sell products very similar to John Doe. The difference? John Doe uses a Goodyear welting method to attach their soles, instead of gluing them on like other manufacturers. This allows you to more easily resole your shoes over and over again, which can extend the life of your shoes considerably (assuming you take care of the uppers). That translates to better value for your money and less junk in landfills. I think everyone can applaud that.

Chelsea Boots
For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).
Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett &amp; Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett &amp; Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal&#8217;s prices are denoted in Malaysian ringgit, so you have to convert them).
Slightly more affordable options can be had through Grenson, Shipton &amp; Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.
For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you&#8217;ll want to be careful to avoid the frumpy versions (I&#8217;m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).
If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano &amp; Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Chelsea Boots

For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).

Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).

Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.

For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).

If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Six Sales I Like

As many readers may know, I put together the sales roundups for our Inside Track. Lately, each week’s post has contained 25-50 sales announcements, and the whole thing takes me hours to put together. On the upside, it means that I get to shop at sales a lot. Not a bad benefit for a guy who enjoys clothing. Here are six sales going on right now that I particularly like, along with a selection of items I’ve been eyeing.  

Roden Gray: These guys just did another price drop yesterday. I really like this Aspesi M65 jacket, which I think would look great with a pair of jeans or chinos. Union in Los Angeles has the same jacket on sale, and there are more colors and sizes available, but the discount is less tempting (they do have nicer pictures though). Also, if you don’t mind the price, this Nanamica jacket is pretty awesome. I picked it up two months ago from Barney’s (who has it on even deeper discount). The quality and fit are hard to tell from online photos, but it’s a wonderfully made piece with a great silhouette. Take another 10% off at checkout with the discount code getgray

UshowU: Both Jesse and I really like Nigel Cabourn, but his stuff is very expensive. The only way I find myself owning his designs is to wait until they go on deep discount, like right now at UshowU. Of the more affordable pieces available, I really like the “granddad henleys.” I own a few and wear them on occasion with leather jackets and jeans. They come in white, green, and British tan

Exquisite Trimmings: Exquisite Trimmings has a bunch of men’s accessories on sale, including some Drake’s ties and pocket squares.  With the right brown sport coat, I think this textured green boucle tie could make for an excellent look this fall. I also like some of the batik pocket squares still kicking around. You can expect another 20% discount at checkout if you don’t have to pay European taxes, and the discount code SF10 will knock another 10% off as well. 

Emmett Shirts: Emmett specializes in shirts, but they also make some pretty nice ties. Some of them are on sale right now at half off, with another 20% taken at checkout if you’re outside of the EU. I like some of the basic blue designs, like this simple pin dot. You’d be hard pressed to find a sport coat or suit that won’t go with this tie. 

Trunk Clothiers: Sizes are limited, but there are some Boglioli suits and sport coatsCommon Projects low tops, and a Nanamica jacket on discount. Boglioli, for those who aren’t familiar, makes a pretty good version of the softly tailored, unstructured sport coat that’s been so popular. As with many of the aforementioned stores, non-EU customers can take another 20% off at checkout.  

Carson Street Clothiers: Carson Street Clothiers just put much of their stock at 50% off. I’ve always liked chukkas for casual wear, and of all the chukkas in the world, I think Loake makes one of the best looking, affordable options. It’s on sale right now at Carson for $200, which is slightly less than what they go for at Pediwear.

What I Take Long Walks In
With the exception of running shoes, the most comfortable shoes I&#8217;ve worn have always been built on Plantation crepe. Crepe refers to a sort of soft rubber - usually slightly yellow-ish in color - that comes in large sheets. Shoe manufacturers take these sheets, cut them down to the size and shape necessary, and then layer them to form a sole. The result is something that&#8217;s very, very comfortable. They make you feel like you&#8217;re walking on soft clouds, or more realistically, like those big rubber pads that toddlers play on. 
The upside to crepe is that they&#8217;re comfortable, particularly on hard concrete, and look suitably stylish for spring through fall wear. The downside is that they might not last as long as a pair of hard-bottom leather soles. Still, they can still be replaced by an experienced cobbler when the time comes. I&#8217;ve also read that crepe can get rigid and crack. I don&#8217;t know if this is because of harsh weather conditions or just plain age, but for what it&#8217;s worth, that&#8217;s never happened to any of my crepe soled shoes. 
There are a number of shoe styles that are commonly made with Plantation crepe - boots, plain toe derbys, moccasins, etc. My favorites are perhaps brown suede chukkas, which I think look particularly nice with cotton trousers, casual shirts, and even the occasional soft-shouldered odd jacket. The pairing of suede and crepe makes for a particularly stylish casual combination, and you can find suede, crepe soled chukkas at a pretty wide range of price points. On the high end, A Suitable Wardrobe has my favorites - a really handsome model that looks sleek enough to be worn with grey wool trousers. For something more casual and affordable, consider Church&#8217;s Sahara, Loake&#8217;s Gobi, or Clarks&#8217; desert boots. The third retails for about $120, but it&#8217;s not hard to find them for under $100. Just Google around or check eBay. 

What I Take Long Walks In

With the exception of running shoes, the most comfortable shoes I’ve worn have always been built on Plantation crepe. Crepe refers to a sort of soft rubber - usually slightly yellow-ish in color - that comes in large sheets. Shoe manufacturers take these sheets, cut them down to the size and shape necessary, and then layer them to form a sole. The result is something that’s very, very comfortable. They make you feel like you’re walking on soft clouds, or more realistically, like those big rubber pads that toddlers play on. 

The upside to crepe is that they’re comfortable, particularly on hard concrete, and look suitably stylish for spring through fall wear. The downside is that they might not last as long as a pair of hard-bottom leather soles. Still, they can still be replaced by an experienced cobbler when the time comes. I’ve also read that crepe can get rigid and crack. I don’t know if this is because of harsh weather conditions or just plain age, but for what it’s worth, that’s never happened to any of my crepe soled shoes. 

There are a number of shoe styles that are commonly made with Plantation crepe - boots, plain toe derbys, moccasins, etc. My favorites are perhaps brown suede chukkas, which I think look particularly nice with cotton trousers, casual shirts, and even the occasional soft-shouldered odd jacket. The pairing of suede and crepe makes for a particularly stylish casual combination, and you can find suede, crepe soled chukkas at a pretty wide range of price points. On the high end, A Suitable Wardrobe has my favorites - a really handsome model that looks sleek enough to be worn with grey wool trousers. For something more casual and affordable, consider Church’s Sahara, Loake’s Gobi, or Clarks’ desert boots. The third retails for about $120, but it’s not hard to find them for under $100. Just Google around or check eBay. 

Finding Affordable Shoes
Shoes may or may not be the most important part of a man’s ensemble, but they can certainly be the veto point. A man can look sharp as a tack in a well-tailored suit, but if he’s wearing dull, square toe shoes, everything was for naught. Unfortunately, nice shoes are expensive. Even the ones commonly recommended as “entry level” brands will retail for $350 or more. So, in an effort to direct readers to where they can find well-made shoes for less, I’ve compiled a list of every place that I know of.
eBay: The most obvious is eBay. We have a customized search link you can use, but you can also employ other methods. Last week, for example, I talked about how Ralph Lauren shoes are some of the hidden gems on eBay, so long as you know how to look for them. The same goes for shoes made by Brooks Brothers. Theirs don’t get as bad as some in Ralph Lauren’s range, but you would still be wise to look for indicators of quality. You can also check out sausages234, an eBay seller who specializes in footwear.
Thrift stores: These will take a little more work than doing a search on eBay, but you could potentially walk away with some better deals. The key is in knowing where to thrift and how to spot quality. Use Jesse’s series on thrifting as a guide.
Good online retailers: There are two online retailers who consistently have some of the most competitive prices around - Pediwear and P.Lal. It would be smart to check with them before you purchase anything, as they&#8217;ll often offer price-matching guarantees. You can also check out A Fine Pair of Shoes. They sell really nice English models, and will discount much of their stock at the end of each season. Finally, Franco’s will often have shoes on sale. Right now there are a bunch of Rider Boots, which are very well made.
Online discount houses: Likewise, there are a bunch of online discount sites. Classic Shoes for Men, Shop the Finest, and Virtual Clotheshorse come to mind (though the last two focus more on the Italian variety). Sierra Trading Post also regularly stocks Trickers. You can knock 30% off or more if you sign up for their DealFlyer newsletter. Different coupons are released every day.
Affordable brands: There are probably more brands than ever before selling well-made, affordable shoes. Here&#8217;s a list:
Loake: Loake makes a few different lines, but the one that’s generally worth buying is their 1880 range, particularly the ones that are Goodyear welted and made with hard-bottom leather soles.
Charles Tyrwhitt: Many of Charles Tyrwhitt’s shoes are made by Loake or equivalent factories. Ignore the lure of sale prices, however. Charles Tyrwhitt’s stuff is always on sale.
Herring: I have no first hand experience with the line, but my understanding is that many of their shoes are also made by Loake (or, again, equivalent factories).
Meermin: One of my favorites of the lot. Their shoes are handwelted, which is believed to be a better construction method than Goodyear welting, and they have a semi-affordable made-to-order program. You can read a review I did of them here.
Shipton &amp; Heneage: Shipton &amp; Heneage sells shoes made by various well-respected manufacturers in England and Italy. Sometimes you’ll find shoes here selling for less than what the original manufacturers would have you pay. Sign up for their Discount Club to receive coupons.
Made in Maine: There are a bunch of quality shoe manufacturers in Maine. The first that comes to mind is Rancourt, who sells handsewn shoes at a very reasonable price. There’s also Town View Leather and Arrow Moccasins, both of whom also sell handsewn shoes, but mostly of the moccasin variety. Those give less foot support, but they can be good for short walks. Additionally, there’s Eastland’s Made in Maine collection. I bought one of their boots last year, and on the inside, there was a strip of reconstituted leather covering the back (where the heel cup would normally go). The leather fell apart after my third wear, and customer service wasn’t terribly helpful, but to be fair, the shoes still wear fine. Finally, a reader of ours suggested Dexter 1957, but I have no first hand experience with them. Reviews online are scant and mixed.
Kent Wang and Howard Yount: Both these companies can usually be relied upon for selling decently made things at lower-than-average prices.
Markowski: I have no first hand experience with this line, but their customers have given positive reports on StyleForum. The shop is based in Paris, but the shopkeepers speak decent English. They also hold sales, which knocks their prices down somewhat even further.
Andrew Lock: Jesse gave a good review of them here (he even had a shoe expert take them apart).
Allen Edmonds factory seconds: The term factory seconds just means shoes that haven’t passed the quality control process, but often the “defects” are incredibly minor (like a very small nick). You can contact Allen Edmonds&#8217; “shoe bank” store in Brookfield, Wisconsin to make a purchase. Their number is (262) 785-6666. 
Suede: Let’s say all the above are still out of range to you. If you can’t afford higher-quality shoes, at least aim for suede. They’ll generally look better with age than a pair made from corrected grain. Perhaps the most affordable suede shoes I know of are Clarks’ desert boots, which sometimes go for as little as $60 on sale. Once you get them, know how to take care of them well, so that you get as much out of your purchase as possible. 

Finding Affordable Shoes

Shoes may or may not be the most important part of a man’s ensemble, but they can certainly be the veto point. A man can look sharp as a tack in a well-tailored suit, but if he’s wearing dull, square toe shoes, everything was for naught. Unfortunately, nice shoes are expensive. Even the ones commonly recommended as “entry level” brands will retail for $350 or more. So, in an effort to direct readers to where they can find well-made shoes for less, I’ve compiled a list of every place that I know of.

eBay: The most obvious is eBay. We have a customized search link you can use, but you can also employ other methods. Last week, for example, I talked about how Ralph Lauren shoes are some of the hidden gems on eBay, so long as you know how to look for them. The same goes for shoes made by Brooks Brothers. Theirs don’t get as bad as some in Ralph Lauren’s range, but you would still be wise to look for indicators of quality. You can also check out sausages234, an eBay seller who specializes in footwear.

Thrift stores: These will take a little more work than doing a search on eBay, but you could potentially walk away with some better deals. The key is in knowing where to thrift and how to spot quality. Use Jesse’s series on thrifting as a guide.

Good online retailers: There are two online retailers who consistently have some of the most competitive prices around - Pediwear and P.Lal. It would be smart to check with them before you purchase anything, as they’ll often offer price-matching guarantees. You can also check out A Fine Pair of Shoes. They sell really nice English models, and will discount much of their stock at the end of each season. Finally, Franco’s will often have shoes on sale. Right now there are a bunch of Rider Boots, which are very well made.

Online discount houses: Likewise, there are a bunch of online discount sites. Classic Shoes for Men, Shop the Finest, and Virtual Clotheshorse come to mind (though the last two focus more on the Italian variety). Sierra Trading Post also regularly stocks Trickers. You can knock 30% off or more if you sign up for their DealFlyer newsletter. Different coupons are released every day.

Affordable brands: There are probably more brands than ever before selling well-made, affordable shoes. Here’s a list:

  • Loake: Loake makes a few different lines, but the one that’s generally worth buying is their 1880 range, particularly the ones that are Goodyear welted and made with hard-bottom leather soles.
  • Charles Tyrwhitt: Many of Charles Tyrwhitt’s shoes are made by Loake or equivalent factories. Ignore the lure of sale prices, however. Charles Tyrwhitt’s stuff is always on sale.
  • Herring: I have no first hand experience with the line, but my understanding is that many of their shoes are also made by Loake (or, again, equivalent factories).
  • Meermin: One of my favorites of the lot. Their shoes are handwelted, which is believed to be a better construction method than Goodyear welting, and they have a semi-affordable made-to-order program. You can read a review I did of them here.
  • Shipton & Heneage: Shipton & Heneage sells shoes made by various well-respected manufacturers in England and Italy. Sometimes you’ll find shoes here selling for less than what the original manufacturers would have you pay. Sign up for their Discount Club to receive coupons.
  • Made in Maine: There are a bunch of quality shoe manufacturers in Maine. The first that comes to mind is Rancourt, who sells handsewn shoes at a very reasonable price. There’s also Town View Leather and Arrow Moccasins, both of whom also sell handsewn shoes, but mostly of the moccasin variety. Those give less foot support, but they can be good for short walks. Additionally, there’s Eastland’s Made in Maine collection. I bought one of their boots last year, and on the inside, there was a strip of reconstituted leather covering the back (where the heel cup would normally go). The leather fell apart after my third wear, and customer service wasn’t terribly helpful, but to be fair, the shoes still wear fine. Finally, a reader of ours suggested Dexter 1957, but I have no first hand experience with them. Reviews online are scant and mixed.
  • Kent Wang and Howard Yount: Both these companies can usually be relied upon for selling decently made things at lower-than-average prices.
  • Markowski: I have no first hand experience with this line, but their customers have given positive reports on StyleForum. The shop is based in Paris, but the shopkeepers speak decent English. They also hold sales, which knocks their prices down somewhat even further.
  • Andrew Lock: Jesse gave a good review of them here (he even had a shoe expert take them apart).

Allen Edmonds factory seconds: The term factory seconds just means shoes that haven’t passed the quality control process, but often the “defects” are incredibly minor (like a very small nick). You can contact Allen Edmonds’ “shoe bank” store in Brookfield, Wisconsin to make a purchase. Their number is (262) 785-6666. 

Suede: Let’s say all the above are still out of range to you. If you can’t afford higher-quality shoes, at least aim for suede. They’ll generally look better with age than a pair made from corrected grain. Perhaps the most affordable suede shoes I know of are Clarks’ desert boots, which sometimes go for as little as $60 on sale. Once you get them, know how to take care of them well, so that you get as much out of your purchase as possible. 

The Charm of Tassel Loafers
I really like tassel loafers. I’m wearing a shell cordovan pair now with brown sharkskin trousers, a dark green v-neck sweater, light blue oxford cloth button-down shirt, navy over-the-calf socks, and a dark reddish-brown alligator belt. With clothes that are a bit too fully cut, tassel loafers can look a little fuddy duddy; with clothes that are too tight, they can look overly hip. Somewhere in the middle, I think, is where they look best.
Tassel loafers came into being in the post-war period of the 1940s, right when tweed jackets, Shetland sweaters, and penny loafers dominated prep schools and Ivy League campuses. As college students graduated, they wanted something as comfortable as their slip-ons, but were a bit dressier and more sophisticated for their new life in the business world. It was around this time that an actor named Paul Lukas came back from Europe with a pair of oxfords. They had little tassels at the end of their laces, which Lukas thought made them look more lively. So he took them to a couple of New York shoemakers to see if they could make something similar, and they in turn took the job to Alden. The company’s president at the time, Arthur Tarlow, came up with tasseled loafers and they were an instant success. That makes Alden’s model the original, and Paul Lukas the first man to wear this style of footwear. You can read more about this wonderful history in this article by Bruce Boyer.
Tassel loafers come in a variety of colors and leathers. The most common is brown calfskin, but the ne plus ultra is the reddish-brown shell cordovan that comes from Chicago’s Horween Tannery. Shell cordovan has the particularly good quality of holding the color burgundy well. In calf, burgundy can sometimes look cheap, but in horsehide leather, it absolutely glows. 
As for where to get them, there are probably a dozens of versions on the market. I’ll only cover a few. As mentioned, Alden&#8217;s is the original and its history as the classic makes it hard to beat. They also make a similar model for Brooks Brothers. The main deviation is the piece of leather that’s added to the heel cup. From England, we have Crockett &amp; Jones&#8217; Cavendish and Edward Green&#8217;s Belgravia. Crockett &amp; Jones also makes a shell cordovan version for Ralph Lauren called the the Marlow, and it has a slightly more unique shade of shell cordovan brown.
My own pair is Allen Edmonds&#8217; Grayson. It’s quite similar to Alden’s, but it has a higher vamp, which is the part the shoe that covers the top part of your foot. I thought it looked slightly better this way, so I bought a pair in shell cordovan. I couldn’t be happier with the purchase and recommend them highly.
If you’d like more affordable options, consider Loake&#8217;s Lincoln and Meermin&#8217;s 101381. Both come in around $175, but Meermin has the added advantage of being able to do special orders. If you’d like to get a pair in shell cordovan or suede, or made from a different last or sole, they’d be happy to make you a pair for a small surcharge. I have a pair of their made-to-order shoes and couldn&#8217;t be more impressed with their value. To order, read this buyer&#8217;s guide and then go to Meermin&#8217;s website. My only comment on that guide is that you should ask Meermin for sizing advice; don&#8217;t just assume. 
Tassel loafers aren&#8217;t anything I&#8217;d call &#8220;an essential,&#8221; but they&#8217;re certainly very enjoyable to wear. If you work in an environment that lets you get away with more casual footwear, try wearing a pair of these with a wool sweater and corduroys, or maybe a checkered tweed and flannel wool trousers. Both will carry a great sense of American style that&#8217;s both casual and sophisticated. 

The Charm of Tassel Loafers

I really like tassel loafers. I’m wearing a shell cordovan pair now with brown sharkskin trousers, a dark green v-neck sweater, light blue oxford cloth button-down shirt, navy over-the-calf socks, and a dark reddish-brown alligator belt. With clothes that are a bit too fully cut, tassel loafers can look a little fuddy duddy; with clothes that are too tight, they can look overly hip. Somewhere in the middle, I think, is where they look best.

Tassel loafers came into being in the post-war period of the 1940s, right when tweed jackets, Shetland sweaters, and penny loafers dominated prep schools and Ivy League campuses. As college students graduated, they wanted something as comfortable as their slip-ons, but were a bit dressier and more sophisticated for their new life in the business world. It was around this time that an actor named Paul Lukas came back from Europe with a pair of oxfords. They had little tassels at the end of their laces, which Lukas thought made them look more lively. So he took them to a couple of New York shoemakers to see if they could make something similar, and they in turn took the job to Alden. The company’s president at the time, Arthur Tarlow, came up with tasseled loafers and they were an instant success. That makes Alden’s model the original, and Paul Lukas the first man to wear this style of footwear. You can read more about this wonderful history in this article by Bruce Boyer.

Tassel loafers come in a variety of colors and leathers. The most common is brown calfskin, but the ne plus ultra is the reddish-brown shell cordovan that comes from Chicago’s Horween Tannery. Shell cordovan has the particularly good quality of holding the color burgundy well. In calf, burgundy can sometimes look cheap, but in horsehide leather, it absolutely glows. 

As for where to get them, there are probably a dozens of versions on the market. I’ll only cover a few. As mentioned, Alden’s is the original and its history as the classic makes it hard to beat. They also make a similar model for Brooks Brothers. The main deviation is the piece of leather that’s added to the heel cup. From England, we have Crockett & Jones’ Cavendish and Edward Green’s Belgravia. Crockett & Jones also makes a shell cordovan version for Ralph Lauren called the the Marlow, and it has a slightly more unique shade of shell cordovan brown.

My own pair is Allen Edmonds’ Grayson. It’s quite similar to Alden’s, but it has a higher vamp, which is the part the shoe that covers the top part of your foot. I thought it looked slightly better this way, so I bought a pair in shell cordovan. I couldn’t be happier with the purchase and recommend them highly.

If you’d like more affordable options, consider Loake’s Lincoln and Meermin’s 101381. Both come in around $175, but Meermin has the added advantage of being able to do special orders. If you’d like to get a pair in shell cordovan or suede, or made from a different last or sole, they’d be happy to make you a pair for a small surcharge. I have a pair of their made-to-order shoes and couldn’t be more impressed with their value. To order, read this buyer’s guide and then go to Meermin’s website. My only comment on that guide is that you should ask Meermin for sizing advice; don’t just assume. 

Tassel loafers aren’t anything I’d call “an essential,” but they’re certainly very enjoyable to wear. If you work in an environment that lets you get away with more casual footwear, try wearing a pair of these with a wool sweater and corduroys, or maybe a checkered tweed and flannel wool trousers. Both will carry a great sense of American style that’s both casual and sophisticated. 

Chukkas for Fall

Fall for me is about boots. Brass-buckled tan jodhpurs worn with olive moleskins; shell cordovan balmoral boots, in that perfect tone of reddish brown, worn with grey flannel trousers; and handsewn, chunky moc-toe boots worn with dark blue jeans. There are dozens of styles, but the most versatile and easy-to-wear of them all is the chukka. Brought over from India by the British Raj, these were named “chukkas” after the playing period in polo. They were quite popular in the 1940s and 1950s, and today can still be worn with a wide range of ensembles – anything from chinos to jeans to wool trousers, put together with something as dressy as a sport coat or as casual a four-pocket field jacket. They can even be worn with suits, although it’s advisable to stick with more “casual” varieties, such as ones made from flannel, linen, or tweed, rather than smooth, lightweight worsted wools.

There are number of good options to consider. For those on a budget, I recommend Loake or Meermin. Loake has two models: the Kempton, which is built on the round toe 026 last, and the Pimlico, which is built on the slightly sleeker, soft-square toe Capital. These are also available rebranded as the Harwood at Charles Trywhitt, as well as the Gosforth and Barrow from Herring. Meermin, on the other hand, has two suede models on their Rui last, which is a round toe design you can more closely inspect here. If you happen to not like the Rui, Meermin can also custom build you a chukka with any last, leather, and sole you wish for a small surcharge. Just drop them a note through their website to order. Their quality is just as good, if not considerably better once you go made-to-order, as Loake’s. 

If you’re willing to spend a little bit more money, there’s a wider range of options. Allen Edmonds, for example, has their Malvern on sale for about $250. For a few hundred dollars more, there’s a number of designs at Crockett and Jones, which you can peruse by doing a search on their website for “chukkas.” My favorite from them is probably the Brecon, a country calf leather boot built on a Dainite sole. It’s a very rustic shoe that can be successfully paired with corduroys, moleskins, and jeans. For something sleeker, check out Kent Wang, who has something similar to the Crockett and Jones’ Tetbury for about $350. Additionally, there’s this handsome shell cordovan version from Alden. If you want one, but can’t afford the price, you can have something similar made through Meermin, custom ordered, for about half the cost.

Of course, those just scratch the surface of the most basic models available. There’s also crepe rubber soled chukkas, which are an incredible pleasure to walk on. Like other well made shoes, these can last years and years if properly taken care of and given regular resolings. Simple, basic designs include Clark’s Desert Boots, Church’s Sahara, Loake’s Campden, and A Suitable Wardrobe’s Easy Fitting Chukka. For something lighter and more breathable, try ones that are unlined. Unlined chukkas lack structure around the uppers, so they feel more like slippers. Models here include Allen Edmonds’ Amok and Alden’s 1494. The Amok is noticeably sleeker, but I find more charm in Alden’s wider 1494 version. Crockett and Jones also has unlined models called the Milton and Hartland, as well as one simply named the “Chukka.” All of those are available for view on their website and for purchase through their New York City store.

Whatever you choose, I encourage you to pick up a pair (if you don’t already own some) and try wearing them this fall with jeans and tweeds, corduroys and Shetland sweaters, and wool trousers and waxed cotton coats. In a smooth brown calfskin or russet shade of suede, these can be some of the most versatile shoes you will ever own.