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.”

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)

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. 

It’s On Sale: Oak Street Bootmakers’ Camp Boots

Oak Street Bootmakers just put their camp boots on 30% discount, which brings the price down from ~$335 to ~$235 (price slightly varies between the two different sole styles). These are made from Horween’s Chromexcel leather, which is a very soft, rich material, and the toes are handstitched using moccasin construction. I own a few of their shoes and love them for casual wear. 

As the site recommends, you’ll want to size down half a size unless you plan to wear these with really, really thick socks. Shipping within the United States is free. 

Three Good Sales

Three good sales started today.

The first is at Drake’s, who just put a selection of their men’s accessories on discount. Note that folks outside of the EU can expect another ~20% off at checkout for not having to pay European taxes.

Next, The J. Peterman Company is offering a “30% off + free shipping” discount with the checkout code WeLoveYouToo. The code drops this Swaine Adeney Brigg umbrella down to $245. Not as cheap as the time Jesse found it for $187, or even when he found it for $234, but it’s been over a year since I’ve seen it go down this low. 

Finally, H.W. Carter & Sons is giving an extra 20% off with the code 0020. That drops these boots by Oak Street Bootmakers down to about $175. They have some other nice casual shoes as well. I own a few Oak Street Bootmakers shoes and really like them. 

Camp Mocs

In the last 100 years or so, Americans have invented some of the most classic slip-on shoe styles for men, but they usually start with an idea borrowed from somewhere else. G.H. Bass, for example, invented the classic American penny loafer, but they came up with the idea after having seen moccasin style shoes made and worn by farmers in Norway. Alden, similarly, came up with the tassel loafer when actor Paul Lukas asked if they could make something similar to a pair of tasseled oxfords he picked up in Europe.

Yet another example is the camp moc, which was invented by LL Bean’s founder, Leon Leonwood Bean, in 1936. He came up with a slip on shoe that could be worn out in the wilderness by taking some ideas from Native American moccasins. Like many of his company’s clothes in the mid-century, LL Bean’s camp mocs eventually made their way to college campuses. At that time, many students liked to repurpose outdoor clothes such as parkas, trail mocs, and camp mocs for everyday use. 

LL Bean still makes their camp moc, but I’m afraid it’s not what it used to be. It’s a decent shoe, to be sure, and probably the most affordable one out there at $79. However, the leather quality leaves a lot to be desired.

If you can afford them, you can find better camp mocs from Oak Street Bootmakers, Rancourt, and Quoddy. Rancourt’s has the advantage in being fully made-to-order, so you can customize them however you’d like. Alden also makes a model through their Cape Cod Collection. It’s typically built on a less than ideal driving sole, but Harrison seems to have it available on a leather sole with a stacked heel (less traditional, but nice looking). I also like the ones from Russell Moccasin (Sid Mashburn has better photos) and Eastland’s Made in Maine. Eastland’s Made in Maine collection is significantly better than their mainline (which also has a camp moc), but to be honest, I find them a bit overpriced for their quality. On the upside, they’ve somehow escaped internet hype, so it’s easier to find them on sale and (occasionally) eBay at heavily discounted prices. Their camp moc is a pretty good value if you can find them half off or so, but note that they’re a bit low on the instep.

Two other good makers are Arrow Moccasins and Town View Leather. They’re both small, family-owned operations that make fully handsewn moccasin style shoes. I like them a lot, especially at their modest price point. They give you the option of making your moccasins with a crepe or double leather sole. I have a pair of double leather sole moccasins from Arrow, and like them for short walks and use around the house. Jesse has also taken his for longer walks. The leathers these guys use is thick and supple, and nicely conform to your feet after a few months worth of use. 

At their core, however, camp mocs are meant to be abused and worn down to the ground. Many of the aforementioned brands make camp mocs from higher-quality leathers, which means they’ll last a bit longer and look better with age. However, even the LL Bean ones have a certain charm as they’re falling apart. Buy ones that are right for your budget and feel free to put some hard use into them.

(Photos via Reddit)