Easy Ways to Look Better in Tailored Clothing
Whether you’re into the “coat-and-tie look” or not, most of us have to wear a suit at some point, and for those times, it’s amazing how much can be done with just a few basic steps. Look at the photo above, for example – two men in suits, but wearing them to very different effects. The man on the left looks great. The man on the right … less great. So much can be done with just a few simple changes. 
Get Your Pants Hemmed
You want your pants hemmed so that there’s either one break, or no break (a break is the small indentation on your pants as your cuff “breaks” over the top of your shoe). You may find, however, that even with properly hemmed trousers, you pants will slip down a little throughout the day, which will ruin those clean, vertical lines. Some simple solutions: wear suspenders, which will keep your pants up at all times; get your waistband and belt adjusted by a tailor, so they fit you better (although, you’ll always experience some slippage with belted trousers); or simply, pay attention to where your pants are and pull them up when need be.
Show a Bit of Cuff
You want about a quarter-of-an-inch of shirt cuff to peek out from your jacket sleeve. There are, however, some complications with this.
First, if your shirtsleeves are too long, you probably don’t want to shorten them. Shirtsleeves need to be a bit long, so that the cuff doesn’t ride up on you as you extend your arm (think of it as having some slack). Instead, you just want your cuffs to stay in the same position, regardless of how you move around. To achieve this, bring your shirt to an alterations tailor and have him or her tighten or loosen the cuff by moving the cuff button. It shouldn’t cost more than a couple of bucks.
Second, if your jacket sleeves are too short or long, you’ll need to have a tailor either let out some material from the edge or take your sleeves up from the cuff. The second process can be complicated by “working buttonholes,” where the buttonholes are actually punched through and not just for show. Don’t skimp here and let that last button sit too close to your sleeve edge. Instead, have your tailor take the sleeve up from the armhole, but know that it’ll add to the cost.  
Wear Better Shoes
Finally, wear better shoes. Ones that are made from full grain leather, not corrected grain. Cheap shoes look bad when they’re new, and worse with wear. Luckily, the market for good, full-grain leather shoes has gotten a lot more competitive over the years, which means the entry price has dropped to about $200. You can start with this list of good brands. I’d add Jack Erwin to that now, although I think you still get a nice jump in quality as you move from them to Meermin, Herring, or Loake (conversely, Jack Erwin is located in the US, so it’s a lot easier to return shoes if need be). If $200 is too much for you, there’s always eBay and thrifting. For eBay, you can use our customized search link or smart shop smartly for Ralph Lauren. To learn how to thrift better, check out Jesse’s three-part guide. 
Doing just those three things won’t make you look like Cary Grant, but they’ll make you look better than most suit-wearing people in the world. To look even better, read Jesse’s very reasonable and easy tips here. To look even better still, learn about the fit and silhouette of tailored clothing.
(Photo via White Hawk Warrior)

Easy Ways to Look Better in Tailored Clothing

Whether you’re into the “coat-and-tie look” or not, most of us have to wear a suit at some point, and for those times, it’s amazing how much can be done with just a few basic steps. Look at the photo above, for example – two men in suits, but wearing them to very different effects. The man on the left looks great. The man on the right … less great. So much can be done with just a few simple changes. 

Get Your Pants Hemmed

You want your pants hemmed so that there’s either one break, or no break (a break is the small indentation on your pants as your cuff “breaks” over the top of your shoe). You may find, however, that even with properly hemmed trousers, you pants will slip down a little throughout the day, which will ruin those clean, vertical lines. Some simple solutions: wear suspenders, which will keep your pants up at all times; get your waistband and belt adjusted by a tailor, so they fit you better (although, you’ll always experience some slippage with belted trousers); or simply, pay attention to where your pants are and pull them up when need be.

Show a Bit of Cuff

You want about a quarter-of-an-inch of shirt cuff to peek out from your jacket sleeve. There are, however, some complications with this.

First, if your shirtsleeves are too long, you probably don’t want to shorten them. Shirtsleeves need to be a bit long, so that the cuff doesn’t ride up on you as you extend your arm (think of it as having some slack). Instead, you just want your cuffs to stay in the same position, regardless of how you move around. To achieve this, bring your shirt to an alterations tailor and have him or her tighten or loosen the cuff by moving the cuff button. It shouldn’t cost more than a couple of bucks.

Second, if your jacket sleeves are too short or long, you’ll need to have a tailor either let out some material from the edge or take your sleeves up from the cuff. The second process can be complicated by “working buttonholes,” where the buttonholes are actually punched through and not just for show. Don’t skimp here and let that last button sit too close to your sleeve edge. Instead, have your tailor take the sleeve up from the armhole, but know that it’ll add to the cost.  

Wear Better Shoes

Finally, wear better shoes. Ones that are made from full grain leather, not corrected grain. Cheap shoes look bad when they’re new, and worse with wear. Luckily, the market for good, full-grain leather shoes has gotten a lot more competitive over the years, which means the entry price has dropped to about $200. You can start with this list of good brands. I’d add Jack Erwin to that now, although I think you still get a nice jump in quality as you move from them to Meermin, Herring, or Loake (conversely, Jack Erwin is located in the US, so it’s a lot easier to return shoes if need be). If $200 is too much for you, there’s always eBay and thrifting. For eBay, you can use our customized search link or smart shop smartly for Ralph Lauren. To learn how to thrift better, check out Jesse’s three-part guide

Doing just those three things won’t make you look like Cary Grant, but they’ll make you look better than most suit-wearing people in the world. To look even better, read Jesse’s very reasonable and easy tips here. To look even better still, learn about the fit and silhouette of tailored clothing.

(Photo via White Hawk Warrior)

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)

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)

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)

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.

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.

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. 

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. 

Champagne Taste on a Beer Budget: A Black Tie Guide

Our Black Tie Guide continues to help you find all the elements of an eveningwear ensemble. Today, we discuss finding the right shoes — at the right price.

Part 3: Formal Footwear

I don’t want to introduce hyperbole, but wearing bad shoes can take the sharp look of a tuxedo and throw it in the Dumpster. Few things are as disappointing as seeing a gentleman going to extraordinary lengths to wear a tuxedo to only see he’s slipped on a pair of cheap, sport-hybrid, corrected-grain, bicycle-toed “dress shoes”. 

Here’s some basic guidance on what to look for in formal footwear:

  • Black calf leather (patent leather optional)
  • Laced shoes should be balmorals; no blüchers
  • Plain-toe and cap-toes are acceptable; avoid brouging and wingtips
  • Opera pumps are an acceptable slip-on; avoid loafers

Some traditionalists would consider opera pumps as the only footwear choice for black tie (Jesse is a fan), but I can sympathize with those of you who have hesitation. Unless you find a way to score a pair cheaply (or you have disposable income), it’s probably not a good purchase as you can’t really wear it outside of formal events. As someone who only finds an excuse once a year to don black tie, it’s probably not practical. 

If you’re looking for a pair, Shipton & Heneage has two options for $245. And Brooks Brothers has their pair for around $450.

For most men, you probably will find the black cap-toe oxford to be the most accessible and affordable option. The cap-toe shoe will be versatile in the rest of your wardrobe for when you wear a regular suit, making it a better value purchase. 

The Allen Edmonds Park Avenue frequently turns up on eBay for prices below $150 — if not significantly cheaper. You can sometimes find them new and on sale at around $200, too. A retail budget option would be Charles Tyrwhitt, which has a full-grain cap-toe oxford for around $150. 

If you’re able to find it, the plain-toe oxford, in my mind, is a preferred option for footwear. Not so formal that it can’t be worn with a regular suit, but the cleaner, sleek look fits better with the tuxedo. You can see Fred Astaire’s pair (given as a gift to Dick Clark for his 50th birthday) above. One can only hope they dance in a tuxedo so often that their shoes look so well worn. 

The cheapest plain-toe oxford I can find is also from Charles Tyrwhitt, at around $200 in patent leather. For around $260 you can get patent leather pairs from Herring or Shipton & Heneage. My favorite though has to be from Kent Wang, whose $350 plain-toe balmorals aren’t patent leather, letting you wear them with a suit.

If you choose to go the laced shoe route, then you should consider buying a pair of black silk shoelaces, like on Astaire’s pair above. I only know of two places you can buy them: from George Cleverley (you’ll have to e-mail them) or from A Suitable Wardrobe’s online store. The cost is about $40 either way, but they definitely elevate the look of even a simple cap-toe shoe to something much more formal. 

-Kiyoshi

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. 

Herring reintroduced their double monkstraps. I wrote about them a few months ago as part of my buyer’s guide on double monks, where I covered something like twenty-seven or so different options. Herrings’ are about $250, which make them one of the cheaper options available (if not the cheapest). You can buy them directly through their website

(big thanks to Henrik for the tip off!)