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)

Vintage Leather Belts
I’m not as experienced as Jesse it when it comes to thrifting, but I do enjoy going to thrift stores. When I go, I often like to browse around for vintage leather belts - the thick kind that you wear with jeans. One of the nice things about buying second-hand is that you can get things with a bit more character. With good leather, you’ll often get something that has aged beautifully. 
Take the above belt, for example. It’s from a webpage Mister Freedom made for their “Ranchero shirts,” which are lovely, but the star of the photograph - at least for me - is the belt sitting in the middle. The variation in the coloring, the scuffing, and the scored design give the belt a certain appeal that modern workwear brands only imitate.
You can find such belts if you hunt around enough. Just visit good thrift stores or flea markets (in the Bay Area, I’d highly recommend Antiques by the Bay, which happens on the first Sunday of every month. Not only do they have a few vendors that sell vintage belts, but there are a ton of other great booths for vintage wares as well). There’s also eBay, of course, but that gets slightly dicier. Vintage leather goods can be of varying quality - either because of the quality of the leather itself, or because of how the item was taken care of throughout the years. Without being able to handle the belt, and without a brand name to go off of, it can be difficult to know what you’re looking at. Still, some of these are quite affordable, so if you get stuck with something less than ideal, it’s at least not a big loss.
The alternative is to buy something new, but from a brand that takes it inspiration from old, vintage designs. RRL and Levi’s Vintage Clothing often have tooled or painted belts that are made to look like they’re from the mid-century. You can find them at workwear-focused stores such as Hickoree’s and Unionmade. They won’t have the kind of patina that an authentic vintage belt will carry, but they’re often still quite handsome. With enough wear, you might get it to look as nice as the one Christophe Loiron (owner of Mister Freedom) photographed above (though, probably not, because that belt looks really awesome). 
(Photo via Christophe Loiron)

Vintage Leather Belts

I’m not as experienced as Jesse it when it comes to thrifting, but I do enjoy going to thrift stores. When I go, I often like to browse around for vintage leather belts - the thick kind that you wear with jeans. One of the nice things about buying second-hand is that you can get things with a bit more character. With good leather, you’ll often get something that has aged beautifully. 

Take the above belt, for example. It’s from a webpage Mister Freedom made for their “Ranchero shirts,” which are lovely, but the star of the photograph - at least for me - is the belt sitting in the middle. The variation in the coloring, the scuffing, and the scored design give the belt a certain appeal that modern workwear brands only imitate.

You can find such belts if you hunt around enough. Just visit good thrift stores or flea markets (in the Bay Area, I’d highly recommend Antiques by the Bay, which happens on the first Sunday of every month. Not only do they have a few vendors that sell vintage belts, but there are a ton of other great booths for vintage wares as well). There’s also eBay, of course, but that gets slightly dicier. Vintage leather goods can be of varying quality - either because of the quality of the leather itself, or because of how the item was taken care of throughout the years. Without being able to handle the belt, and without a brand name to go off of, it can be difficult to know what you’re looking at. Still, some of these are quite affordable, so if you get stuck with something less than ideal, it’s at least not a big loss.

The alternative is to buy something new, but from a brand that takes it inspiration from old, vintage designs. RRL and Levi’s Vintage Clothing often have tooled or painted belts that are made to look like they’re from the mid-century. You can find them at workwear-focused stores such as Hickoree’s and Unionmade. They won’t have the kind of patina that an authentic vintage belt will carry, but they’re often still quite handsome. With enough wear, you might get it to look as nice as the one Christophe Loiron (owner of Mister Freedom) photographed above (though, probably not, because that belt looks really awesome). 

(Photo via Christophe Loiron)

Deck Jackets

I probably should have anticipated this before I started a blog called Die, Workwear!, but as we get closer to winter, I’ve been thinking about getting myself a deck jacket. The term deck jacket refers to heavy winter coats worn by sailors during the mid-20th century. They’ve become highly prized among vintage collectors and workwear aficionados, not only for their history, but also their durability and protective warmth.

Some of the earliest deck jackets looked very much like the US Army’s winter combat jacket (also known as a tanker jacket). It had a dark blue outer shell made out of a heavy corded cotton, and a basic zipper-front design. Over the years, however, it’s been improved upon by the US military for naval use. In 1943, for example, the jacket was lengthened and lined with alpaca fur so that it’d be more protective for sailors. The knit waistband, exposed knit cuff, and patch pockets were also done away with, as they were at risk of snagging on different parts of the ship. As replacements, the knit cuffs were brought in, sort of like the storm cuffs you see today on certain Barbour jackets, and the jacket’s hem was made with a drawstring. The basic zipper front also saw the addition of a button-closure wind flap, and then later metal hook claps, which were easier to operate when you had big gloves on.

There are still many makers of deck jackets today, and they typically come in the garment’s original colors - dark blue, light olive, and dark green. My favorite version is probably by Mister Freedom, who released one with a striped blanket lining a few years ago. Most sizes have long sold out on their website, but you can sometimes find some floating around on eBay. Other makers include the many Japanese companies that specialize in workwear and military reproductions, such as Buzz Rickson, Toys McCoys, The Real McCoys, and The Few. You may also want to look into stores such as Blue in Green, Self Edge, Superdenim, and Bench & Loom, who either carry those aforementioned brands, or similar ones.

Unfortunately for me, all those are well outside my budget. I’ve seen slightly more affordable models by Spiewak, Engineered Garments, Orvis, and Pike Brothers, but they’re still pretty pricey. Going vintage here won’t yield any more savings, as collectors have been hunting for originals on eBay for years. For a good vintage piece, you can expect to pay anywhere from $300 to a whooping $1,500.

So for now, no deck jacket for me. Perhaps for the better, since I don’t think you can look like a sailor with a size 36 chest. 

(Pictures above from Secret Forts, Superfuture member Five, Christophe Loiron, and Good Wear Leather)

Six Great Types of Shirts for Fall

For nearly a century now, the most basic dress shirt for men is a solid white or light-blue button-up, made from 100% cotton, and usually coming in a plain or twill weave. It’s the default choice for dress shirts – something you can rely on year-round to look decent and acceptable, and is very rarely the wrong choice, assuming you’re dressing classically. 

There are times, however, when choosing something a bit different can yield a more harmonious look. Take, for example, the advantage of combining an airy, light-blue linen shirt with a tan cotton sport coat. The two textures are equally casual, and together, they lend a better presentation for summer. Similarly, a fine cotton dress shirt can look puny when set against a hardy Shetland tweed or mid-waled corduroy jacket. Better to pick something with more texture and “weight,” such as these following options, which I think make for excellent fall and winter shirts.

Flannels 

At the top of the list are flannels, which can come in a variety of forms. They can be solid or patterned (if patterned, usually checked), and made from either a softly brushed pure cotton or some kind of wool/ cotton blend. Viyella is particularly famous for their flannel shirtings (the word “shirtings” means “fabrics intended for shirts;” it is not a synonym for the word “shirts”). You can find them at a number of places, such as Dann Online, J. Press, and O’Connell’s. I unfortunately can’t say how any of those fit, but my guess is “traditional.” If you have a custom shirtmaker, they may also carry Viyella fabrics, which you can ask for by name.

Bold cotton plaids

Bold cotton plaids are different from flannels in that they don’t have that soft, brushed quality. They’re smooth like a fine cotton dress shirt, but remain a bit more autumnal through their patterns. Our advertiser Ledbury carries some through their short-run collection (they’ve got more coming down the pipeline, as they’re releasing a new short-run shirt every day this month). Brooks Brothers also has some designs, though mostly in non-iron fabrics, and Gant Rugger might be a good option for younger men. For something more affordable, there’s J. Crew. Just wait for one of their many sales. 

Tattersalls

Tattersalls are symmetrical, thin-lined checks, usually made up of two colors for the lines and a plain-colored background. I find they’re a nice compromise between the dressiness of a standard dress shirt and the casualness of a bold cotton plaid. For something dressier still, you can go for a graph check shirt, which is exactly what it sounds like – a shirt with a pattern that looks like graph paper. Either would do well underneath a tweed or corduroy jacket, and you can find them at places such as Ralph Lauren, Brooks Brothers, and TM Lewin.

Oxford Cloth Button-Downs (aka OCBDs)

OCBDs are versatile enough for year-round wear, but also have the weight and texture necessary to look great underneath fall jackets. What’s not to like? You can read my long-winded series about them here, or just skip to my recommendations.

Chambray

Another good year-round shirt that really comes into its own during the fall and winter seasons. You can find nice high-end options at Self Edge, Rising Sun, and Blue in Green. Mr. Porter also has some designer offerings, and J. Crew is again good for something more affordable (just wait for a sale). My favorite, however, is by Mister Freedom. I appreciate the emphasis they put into beautiful fabrics, and have found mine to age exceptionally well. When choosing one, keep in mind the kind of outerwear you might want to wear. Very casual chambray shirts with extra detailing should be kept with very casual outerwear, rather than traditional sport coats. 

Corduroys

Corduroy shirts are less versatile than any of the above options, but they’re nice to have if you’d like some more variety. Our advertiser Ledbury has one in brown coming out this month (it’s pictured above) and I like that it has a traditional looking collar and lowered second button (good for when you’re wearing the shirt casually and don’t want it buttoned all the way up). For something available now, there’s Michael Bastian, Beams Plus, and LL Bean.