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)

Five Tips For Polishing Shoes
I spent a little bit of time this weekend polishing an old pair of chukkas of mine. Though their pebble grain texture makes them feel more like fall/ winter boots, I’ve been wearing them a lot this summer. They just go too well with jeans.
Polishing shoes is simple enough. Take out the shoelaces and insert some shoe trees, so you have a hard surface to work on. Next, use an old rag to apply some leather conditioner (Saphir is nice, but I mostly use Allen Edmonds’ Conditioner and Cleaner). Then, apply your cream polish with a dauber (I use Saphir for polish, which our advertiser The Hanger Project sells, but you can also get nice results with Meltonian). Finally, brush your shoes out with a large horsehair brush to raise a shine. That, more or less, is the basic process of how to shine shoes. 
There are some things that I think can help improve your technique, however.
1. Brush your shoes down with a large horsehair brush before applying any conditioner. This will remove any specks of dust or dirt that can otherwise mar the leather.
2. I add a layer of wax polish on most of my shoes (almost everything except loafers, camp mocs, and boat shoes). This gives them a higher shine and an extra layer of protection. If you decide to use wax polish, brush down your shoes with a big horsehair brush first. This will even out your cream polish and give you a nicer surface to build a wax layer upon.
3. Also, if you use a wax polish, wipe your shoes down with a leather cleaner every once in a while, as wax can build up and make it difficult for your leather to absorb conditioner. Don’t go crazy though. Leather cleaner is powerful stuff, and you don’t want to damage your shoes’ uppers by scrubbing. Some gentle swipes with a soft cloth will do.
4. Most people try to match the color of their shoe polish as closely as possible to their shoes’ uppers. I actually often go one shade darker, as I find that helps build a bit more “depth” in the color, and makes for a more interesting patina. I’ve also heard of people using black polish for dark brown shoes and navy polish for black shoes. Choose according to your taste, but don’t be afraid to experiment a little. 
5. Finally, the most important tip of all: Always wait a while in between each of your steps. Wait for the conditioner to soak in before you apply cream polish. Wait for the cream polish to dry before you apply wax. Wait for the wax polish to settle before you buff everything out with a large brush. This is not only better for your shoes but it also makes the process of buffing much easier.
(Pictured above: Saphir cream and wax polishes, Edoya horsehair brush,  Crockett & Jones’ Brecon chukkas)

Five Tips For Polishing Shoes

I spent a little bit of time this weekend polishing an old pair of chukkas of mine. Though their pebble grain texture makes them feel more like fall/ winter boots, I’ve been wearing them a lot this summer. They just go too well with jeans.

Polishing shoes is simple enough. Take out the shoelaces and insert some shoe trees, so you have a hard surface to work on. Next, use an old rag to apply some leather conditioner (Saphir is nice, but I mostly use Allen Edmonds’ Conditioner and Cleaner). Then, apply your cream polish with a dauber (I use Saphir for polish, which our advertiser The Hanger Project sells, but you can also get nice results with Meltonian). Finally, brush your shoes out with a large horsehair brush to raise a shine. That, more or less, is the basic process of how to shine shoes. 

There are some things that I think can help improve your technique, however.

1. Brush your shoes down with a large horsehair brush before applying any conditioner. This will remove any specks of dust or dirt that can otherwise mar the leather.

2. I add a layer of wax polish on most of my shoes (almost everything except loafers, camp mocs, and boat shoes). This gives them a higher shine and an extra layer of protection. If you decide to use wax polish, brush down your shoes with a big horsehair brush first. This will even out your cream polish and give you a nicer surface to build a wax layer upon.

3. Also, if you use a wax polish, wipe your shoes down with a leather cleaner every once in a while, as wax can build up and make it difficult for your leather to absorb conditioner. Don’t go crazy though. Leather cleaner is powerful stuff, and you don’t want to damage your shoes’ uppers by scrubbing. Some gentle swipes with a soft cloth will do.

4. Most people try to match the color of their shoe polish as closely as possible to their shoes’ uppers. I actually often go one shade darker, as I find that helps build a bit more “depth” in the color, and makes for a more interesting patina. I’ve also heard of people using black polish for dark brown shoes and navy polish for black shoes. Choose according to your taste, but don’t be afraid to experiment a little. 

5. Finally, the most important tip of all: Always wait a while in between each of your steps. Wait for the conditioner to soak in before you apply cream polish. Wait for the cream polish to dry before you apply wax. Wait for the wax polish to settle before you buff everything out with a large brush. This is not only better for your shoes but it also makes the process of buffing much easier.

(Pictured above: Saphir cream and wax polishes, Edoya horsehair brush,  Crockett & Jones’ Brecon chukkas)

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.