The Language of Penny Loafers

As the weather gets warmer and we inch closer to summer, I most look forward to when I can wear my penny loafers again. I pair them with everything – linen suits, wool trousers and sport coats, chinos and madras shirts, and even the occasional pair of jeans and a button-up. While the style is versatile, however, every pair of pennies may not be. I find that the ones that look best with tailored clothes, for example, don’t go that well with jeans. The difference is all in the detailing.

Toe Construction

Every pair of penny loafers has a U-shaped ridge that bounds the top of the toe. On my dark brown calf Edward Greens, this ridge is made with a decorative top stitch that results in a very clean line. On my dark brown suede Rancourts, the uppers and sides are handsewn together to form what’s known as a “moc toe” (moc being short for moccasin). It’s a slightly rougher looking line, and this roughness only becomes more so with time, as moc toes tend to loosen with wear. Finally, my tan-suede Ralph Laurens have the most prominent ridge of all, with the top piece of the leather folded down and stitched to the sides.

Generally speaking, the last two styles are a bit more casual than the first, if only because they’re rougher and more prominent looking. I find that they go better with slim chinos or jeans, but if you have a more casual sensibility with tailored clothing, they could work with those styles as well. Conversely, the decorative skin stitch technique tends to be the dressiest. You can see this a bit more easily when you compare those Rancourts above to these Aldens. Both are very American in style, but the Aldens are just a tad dressier.

Toe Box Shape

All things being equal, the sleeker the toe box, the dressier the shoe. In this regard, my dark brown calf Edward Greens are the dressiest, while the dark brown suede Rancourts are the most casual.

Color and Material

Like with all shoes, black and dark browns tend to look dressier, while lighter colors (and non-traditional colors) will look more casual. Calf also tends to be dressier than shell cordovan or suede. This is especially true over time, as suede “balds” with wear. This is because, while you can hide scuffs on calf with shoe polish, there’s little you can do about scuffs on suede. This isn’t a bad thing, as quality shoes look better well-worn, but it does mean that wear tends to show up more on suede than anything else.

It’s easy, when choosing a penny loafer, to find yourself drawn to whatever looks dressiest and sleekest, but beware. While those styles may suit you, it’s useful to think hard about what you might wear your loafers with. If it’s something like chinos or jeans, you might do better with something made with a moc toe or beefroll (beefrolls refer to the visible stitching on the sides of the penny strap, which resemble a cut of beef tied with cooking string). There’s language in penny loafers that will dictate how you can best wear your shoes. As Charles Eames once said, “The details are not the details. They make the design.”

Cheap Shoes That Age Well
Although I wouldn’t call it a “rule” for myself, when I can, I try to buy things that I think will look better with time, rather than worse. That is, after all, why most of us value full grain leather shoes over corrected grain ones. It’s not because they’re cheaper in the long run (because they’re not). It’s because high quality shoes acquire a beautiful worn in look that only good materials and years of wear can impart. Shoes made from corrected grain leather, on the other hand, look terrible new and even worse with time.
Unfortunately, shoes that age well are typically expensive. The exception to this is canvas sneakers, which always look better with a bit of dirt and grass staining. Think:
Converse Chuck Taylors and Jack Purcells
Vans Authentics and Classic Slip-Ons
Superga 1705 and 2750
Sperry Top-Sider’s striped CVOs
Tretorn Nylites
All of these retail for under $75, but can be had for less than $50 if you wait for sales.
The best thing about these shoes isn’t their price, however. It’s their designs. Most have been around for decades and their designs are hard to improve on. Take Maison Martin Margiela’s interpretation of Vans’ slip-ons, for example. The heavier look and feel of leather doesn’t evoke the airiness of summer like canvas, even if the design itself looks more luxurious. Similarly, Nigel Cabourn’s interpretation of Chuck Taylor All Stars has a nice retro feel, but truth be told, I think the standard model today is hard to beat.
You can wear these with any number of spring or summer ensembles. I often wear my Chuck Taylor high tops with a white t-shirt, leather jacket, and pair of jeans, and my Superga 1705s with chinos and a madras shirt. On a cooler spring day, the madras shirt gets swapped out for a sweatshirt and light parka. Neither of these feel like compromises over full grain leather shoes, and they’re appreciably much cheaper. It’s nice that good things don’t always have to be expensive. 

Cheap Shoes That Age Well

Although I wouldn’t call it a “rule” for myself, when I can, I try to buy things that I think will look better with time, rather than worse. That is, after all, why most of us value full grain leather shoes over corrected grain ones. It’s not because they’re cheaper in the long run (because they’re not). It’s because high quality shoes acquire a beautiful worn in look that only good materials and years of wear can impart. Shoes made from corrected grain leather, on the other hand, look terrible new and even worse with time.

Unfortunately, shoes that age well are typically expensive. The exception to this is canvas sneakers, which always look better with a bit of dirt and grass staining. Think:

All of these retail for under $75, but can be had for less than $50 if you wait for sales.

The best thing about these shoes isn’t their price, however. It’s their designs. Most have been around for decades and their designs are hard to improve on. Take Maison Martin Margiela’s interpretation of Vans’ slip-ons, for example. The heavier look and feel of leather doesn’t evoke the airiness of summer like canvas, even if the design itself looks more luxurious. Similarly, Nigel Cabourn’s interpretation of Chuck Taylor All Stars has a nice retro feel, but truth be told, I think the standard model today is hard to beat.

You can wear these with any number of spring or summer ensembles. I often wear my Chuck Taylor high tops with a white t-shirt, leather jacket, and pair of jeans, and my Superga 1705s with chinos and a madras shirt. On a cooler spring day, the madras shirt gets swapped out for a sweatshirt and light parka. Neither of these feel like compromises over full grain leather shoes, and they’re appreciably much cheaper. It’s nice that good things don’t always have to be expensive. 

Rubber Soles in Wet Weather
It’s been raining like crazy in the Bay Area, which has made me appreciate how much better rubber soles are on wet ground. The leather uppers on shoes can be made to take the rain quite easily. With calf or shell cordovan, you just have to apply a thin layer of wax polish. With suede, you can use some kind of weatherproofing spray. Either will make your shoes fairly water resistant (although not waterproof), but there are some caveats. With shell cordovan, for example, small little bumps can appear after the leather has been wet, but those can be brushed out with a horsehair brush. In fact, I mostly use a pair of shell cordovan boots as my rain boots. 
While leather shoes can be used in the rain, ones with leather soles often can not. It’s not so much that leather doesn’t provide much traction (because it does), it’s more that untreated leather can soak up water and break down easily when wet. That’s why you need to give your shoes a day of rest in between each wear — it’s so that the perspiration from your feet can dry out and not damage the leather. Imagine, then, what’s happening as your leather soles are soaking up rainwater and grinding against hard pavement and possibly road salt. 
There are a number of good options for rubber soles. Studded Dainites are the best alternative if you want to keep to a “dressier” look. They’re suitable on anything but the dressiest of shoes. Commando and Ridgeway soles are similar, but are probably best kept to chunkier looking styles. Plantation crepe is fine, so long as you don’t wear the ones that are combination of crepe and leather, as the leather tips can peel back when wet. Neoprene cork and white Christy soles are also good, as they provide nice traction and don’t have leather mid-soles you have to worry about. 
If you happen to wear leather soles on a rainy day, make sure they’re dry before you wear them out again. You can set your shoes on their side to let air circulate around the soles, thus helping them dry faster. Just don’t try to speed up the process by setting your shoes near a heater. That will dry out the uppers and cause them to crack, which is much worse than prematurely wearing down the soles. 
(Photo via John Dear)

Rubber Soles in Wet Weather

It’s been raining like crazy in the Bay Area, which has made me appreciate how much better rubber soles are on wet ground. The leather uppers on shoes can be made to take the rain quite easily. With calf or shell cordovan, you just have to apply a thin layer of wax polish. With suede, you can use some kind of weatherproofing spray. Either will make your shoes fairly water resistant (although not waterproof), but there are some caveats. With shell cordovan, for example, small little bumps can appear after the leather has been wet, but those can be brushed out with a horsehair brush. In fact, I mostly use a pair of shell cordovan boots as my rain boots. 

While leather shoes can be used in the rain, ones with leather soles often can not. It’s not so much that leather doesn’t provide much traction (because it does), it’s more that untreated leather can soak up water and break down easily when wet. That’s why you need to give your shoes a day of rest in between each wear — it’s so that the perspiration from your feet can dry out and not damage the leather. Imagine, then, what’s happening as your leather soles are soaking up rainwater and grinding against hard pavement and possibly road salt. 

There are a number of good options for rubber soles. Studded Dainites are the best alternative if you want to keep to a “dressier” look. They’re suitable on anything but the dressiest of shoes. Commando and Ridgeway soles are similar, but are probably best kept to chunkier looking styles. Plantation crepe is fine, so long as you don’t wear the ones that are combination of crepe and leather, as the leather tips can peel back when wet. Neoprene cork and white Christy soles are also good, as they provide nice traction and don’t have leather mid-soles you have to worry about. 

If you happen to wear leather soles on a rainy day, make sure they’re dry before you wear them out again. You can set your shoes on their side to let air circulate around the soles, thus helping them dry faster. Just don’t try to speed up the process by setting your shoes near a heater. That will dry out the uppers and cause them to crack, which is much worse than prematurely wearing down the soles. 

(Photo via John Dear)

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)

A beautiful short documentary about Nicolás Lizares, a huarachero (huarache maker) from Jalisco, Mexico. My mom happens to be in Jalisco right now, staying in Guadalajara, the state’s capital, and she’s bringing back some huaraches for me to wear this summer. Hopefully I can offer a full report at some point.

The video comes via the wonderful site Huarache Blog, which has further information about Sr. Lizares and his shoes here.

The Wall Street Journal has a feel-good story on the resurgence of Northampton-based shoemaking, which is thriving, largely driven by sales in foreign markets—many of them the very countries to which Northampton exported jobs in the 1980s.

The Wall Street Journal has a feel-good story on the resurgence of Northampton-based shoemaking, which is thriving, largely driven by sales in foreign markets—many of them the very countries to which Northampton exported jobs in the 1980s.

How I Learned to Stop Worrying and Love the Wear

Like anyone who feels guilty about how much they’ve spent on their shoes, I’m fairly good at taking care of my footwear. I apply cream and wax polishes every few weeks, and leather conditioner even more frequently. Before any pair goes out for wearing, it gets brushed down to remove any dust or dirt.

I’ve learned, however, that some shoes look better the less you take care of them. This includes work boots, engineer boots, camp mocs, boat shoes, and almost anything that’s considered extremely casual. These still get treated to leather conditioner, just not that often (maybe once every six months to a year). Things such as cream and wax polishes, however, never get used, and shoe trees never get inserted. If you’ve ever wondered whether these things really make a difference, just try going without them for a year. You’ll see that creases develop more quickly and set on deeper when they do. Scuffs and scars will also show up more without the “cover-up” of polish. 

For certain shoes, however you want this kind of “damage” to appear. It gives them character and makes them more lived-in. This gets back to a very fundamental idea that nothing looks good when it’s too new or too stiff. That doesn’t just go for certain styles of footwear – it goes for things such as tweed jackets, briefcases, and almost all kinds of outerwear. It’s perhaps for this reason why there are stories about how Fred Astaire used to throw his new bespoke suits up against the wall before wearing them, and how Charlie Davidson of The Andover Shop won’t even wear a new jacket until it’s been sitting on a hanger for a year. 

Of course, with dressier shoes, careful polishing, edge dressing, and even the occasional bulling can be great. Those will give your shoes a certain kind of luster that’s in keeping with the style. With everything else, however, all you need really is the occasional treatment of leather conditioner. As you can see in the last photo, as long as you buy shoes of good quality - and keep the leather supple so it doesn’t crack - they can be repaired to good effect. And why would you want to recraft an old pair of boat shoes when new ones can be bought for not much more money? Because the old ones look a lot better.   

(Photos via Andrew Chen of 3sixteen, Mister Freedom, Oak Street Bootmakers, and Rancourt)

Woohoo! I finally know how wooden shoes are made! THE SECRET IS POPLAR: EASY TO CARVE AND FREE OF KNOTS!

Reader A.M. points us to this really interesting little article on Reddit, cataloging the moccasin manufacturers of Maine, and the Maine-style moccasin manufacturers of the rest of the country. They range from large (Rancourt hand-sews a thousand pairs a week) to small (like Wassookeag, whose mocs are pictured above).
(The author of the piece is a member of a new reddit community for shoe nerds: /r/goodyearwelt.)

Reader A.M. points us to this really interesting little article on Reddit, cataloging the moccasin manufacturers of Maine, and the Maine-style moccasin manufacturers of the rest of the country. They range from large (Rancourt hand-sews a thousand pairs a week) to small (like Wassookeag, whose mocs are pictured above).

(The author of the piece is a member of a new reddit community for shoe nerds: /r/goodyearwelt.)

Dealing with Salt Stains
One of the big dangers for shoes in the winter is salt stains. When roads become icy and salt gets put down, the resulting slush can seep into shoes and leave salt at the high-water mark. If this salt isn’t taken out, it can leave a permanent line in the leather, much like how scum is left after a receding tide.
If you do get salt on your shoes, you should let them dry naturally and wipe them down the next day with a 50/50 mixture of water and white vinegar. When you do, you’ll notice your shoes considerably darken. This is OK, as the leather is just soaking up the solution. Just rub along where the salt has gathered and you’ll be able to take it out before it does any real damage. Afterwards, let them dry naturally again before putting on some leather conditioner and giving them a layer of wax polish. This should give them a minimal amount of protection next time you go out.
Truthfully, as simple as this sounds, this process can become a bit of a chore if you live in an area with long winters. So the other solution is to wear shoes you don’t have to worrying about staining. Work boots are particularly good in this category, such as those made by Red Wing (the Beckman, Iron Ranger, 875, and 877 models are particularly nice), Wolverine (1000 Mile is the standard), and Chippewa (J. Crew has some models on sale right now for 30% off). I also recently picked up some brown “trench boots” from Oak Street Bootmakers. Their model is a bit more expensive, but I find the shape less clunky and the shoes easier to break-in.
Pictured above is the same trench boot model, but in Oak Street’s “natural Chromexcel” leather, which they source from Horween. These were worn through Chicago’s last winter and purposefully put through a bunch of snow and puddles in heavily salted areas. Horween’s Chromexcel is a particularly “oily” material, so it doesn’t get salt stains easily, but even here you can see that what “damage” has been done only makes the boots look better. 
Of course, you can only wear work boots with certain clothes, so if you need to wear a suit everyday for work, you might just have to put a little more time into your shoe care regime. But, if you don’t, wear shoes you don’t have to worry about ruining. Some shoes look better a bit beat up. 

Dealing with Salt Stains

One of the big dangers for shoes in the winter is salt stains. When roads become icy and salt gets put down, the resulting slush can seep into shoes and leave salt at the high-water mark. If this salt isn’t taken out, it can leave a permanent line in the leather, much like how scum is left after a receding tide.

If you do get salt on your shoes, you should let them dry naturally and wipe them down the next day with a 50/50 mixture of water and white vinegar. When you do, you’ll notice your shoes considerably darken. This is OK, as the leather is just soaking up the solution. Just rub along where the salt has gathered and you’ll be able to take it out before it does any real damage. Afterwards, let them dry naturally again before putting on some leather conditioner and giving them a layer of wax polish. This should give them a minimal amount of protection next time you go out.

Truthfully, as simple as this sounds, this process can become a bit of a chore if you live in an area with long winters. So the other solution is to wear shoes you don’t have to worrying about staining. Work boots are particularly good in this category, such as those made by Red Wing (the Beckman, Iron Ranger, 875, and 877 models are particularly nice), Wolverine (1000 Mile is the standard), and Chippewa (J. Crew has some models on sale right now for 30% off). I also recently picked up some brown “trench boots” from Oak Street Bootmakers. Their model is a bit more expensive, but I find the shape less clunky and the shoes easier to break-in.

Pictured above is the same trench boot model, but in Oak Street’s “natural Chromexcel” leather, which they source from Horween. These were worn through Chicago’s last winter and purposefully put through a bunch of snow and puddles in heavily salted areas. Horween’s Chromexcel is a particularly “oily” material, so it doesn’t get salt stains easily, but even here you can see that what “damage” has been done only makes the boots look better. 

Of course, you can only wear work boots with certain clothes, so if you need to wear a suit everyday for work, you might just have to put a little more time into your shoe care regime. But, if you don’t, wear shoes you don’t have to worry about ruining. Some shoes look better a bit beat up.