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)

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.