Inside the “World’s Fair of Footwear,” Where Shoemaking Gets Obsessive

Twenty minutes is a long time to watch someone polish a shoe. I know, because on Saturday afternoon I watched three people do it.

The occasion? The Championships of Shoe Shining (Americas edition). Each finalist got a factory-new shoe, a kit of Saphir Médaille d’Or wax and brushes, and a timer. With setup and judging, it ran about half an hour, and yes, it was a little silly.

It was also genuinely cool.

The shoes went from a dull brown to a genuine mirror-shine, the kind that looks like it’s straight out of old Hollywood. Jeriah Rocha of Tulsa (who runs a shoe-care business called, perfectly, The Scuff Doctor) took the title, $500, and a pair of Bridlens. Second place went to Josh Swidler, a fourth-grade teacher from Seattle, and Mario Cesar Samaniego of Pharr, Texas, took third.

That was just a side event at Stitchdown Expo, which took over a Chicago event space on November 6 and 7 to trot out some of the coolest shoes an enthusiast could ask for. One look at the crowd told you the story. Half the room was rocking perfectly coiffed suits and oxfords. The other half stomping along in selvedge and glorious lumberjack-tier boots. Both halves were there for a reason. Footwear.

Stitchdown, the footwear media company founded by Ben Robinson, held this thing in Chicago last year as Boot Camp, and it leaned toward the rugged side of things. This year, it got a new name and a new roommate: the Super Trunk Show, a classic dress-shoe gathering run by Kirby Allison, Shoegazing, and The Shoe Snob. The lads packed up their own event in New York and moved it to Chicago to join in.

“The community and the makers showing up pushed the event well beyond what that original name could capture,” Robinson said in announcing the change. Translation: the boot guys and the oxford guys finally have a party in common.

You could see the pedigree on the floor. Nicks, one of the presenting sponsors, had a big zone on the top floor, timed perfectly to the Spokane bootmaker’s launch of a new line called Simply Good Boots. Workwear titan Red Wing was there too, naturally, and so were the tanneries that supply pretty much everyone else: Chicago’s own Horween; S.B. Foot, the Minnesota tannery that still makes leather for Red Wing; and Pennsylvania’s Wickett & Craig. Leather and sole salespeople even worked the aisles pitching the bootmakers, making it a consumer show that’s also a trade show.

With all due respect to the bootmaking greats, one of the best reasons to go was the independent sellers, because nearly every booth was doing fittings. It’s hard to emphasize just how much better a shoe-buying experience can be when you have a pro there taking your Brannock measurement. Or even a full foot outline, in the case of the full-custom guys.

Speaking of things like “Brannock,” shoemaking has plenty of jargon. Here’s a quick cheat sheet:

• Last: The foot-shaped form a shoe is built around. It decides the fit and shape, which is why your size in one boot can be wrong in another, even from the same brand.
• Brannock: That metal sizing device from every shoe store you’ve ever been in. It measures length, width, and arch.
• Goodyear welt: A strip of leather stitched around the edge of the boot, with the sole stitched to that. It’s sturdy, it’s structured, and it lets a cobbler swap the sole out (again and again).
• Stitchdown: The upper is flared outward and stitched straight down to the sole. It’s simpler, flexible, and a classic for work boots. Also resoleable, and yes, it’s where the expo got its name.

I tried on more boots than I can even remember (occupational hazard) and some of my favorites included a pair from Caswell, a Virginia-based brand that sells classic dressy and workwear boots. I tried the Lisbon Stitchdown, with a price tag in the mid-$400s; Caswell says it runs a little big, with a D width roomy enough for plenty of E-width feet. On my foot? Just right.

The display that really surprised me belonged to Johnny Works, where the eponymous bootmaker who goes simply by Johnny sold boots made by hand in Guangzhou, China. Johnny says that he already had American customers ordering from overseas (which is how Stitchdown found him) and his boots lean toward American heritage with some European touches.

Through a translator, he told me that most of his obsession goes into the last, which he’s reworked through version after version to make it more comfortable. Interesting note: Asian lasts tend to be shorter and wider than Western ones, Johnny said. Ten or twenty years ago, “Made in China” meant cheap, but now, he said he’d put China’s best bootmakers alongside, or above, even some of the ultra-luxe Japanese brands. 

“It’s not like Chinese is always a lower tier and Japanese is always high up,” he said. Having tried a pair on, I’m inclined to agree.

Upstairs, Crown Northampton, family-run in England since 1908, hawked individually made-to-order pairs with a nine-to-12-week wait. Its leather sneakers start at $455, shell cordovan runs past $1,100, and US prices include duties and tariffs, so at least that’s a little less math you have to do.

Then there was Russell Moccasin, a bench-made bootmaker from Berlin, Wisconsin, that’s been at it for more than 125 years. Its Heritage Club lets you build a made-to-order boot down to the leather and sole (often S.B. Foot’s Timberjack, from the same tannery a few booths down). The catch? It’s open only to returning customers. The reward for buying a great pair of boots is being allowed to order the next one.

The unfortunate reality of owning a pair of kick-ass kicks is that, eventually, you’re going to want to shape them up again. Enter Saphir, the century-old French polish brand behind the shine-off, which had its full line on hand. A few aisles over was Steve Doudaklian of Bedo’s Leatherworks, a Virginia cobbler with a serious YouTube following, who resoles boots mailed in from all over the world. 

Big brands do this too (Danner has rebuilt thousands of pairs in Portland), but independent cobblers will have a lot more flexibility on what they can offer. I’ve owned resoleable boots for years and never worked up the nerve to ship off a pair. Now that I’ve seen some cobbling in action, that’s about to change.

All in all, there was more to do than I could knock out in a few hours, but as a guy with an unusual foot size and a passion for craftsmanship, my feet had never felt more seen. If that’s you too, Stitchdown Expo returns to Chicago November 5–6, 2027. Leave the flip-flops at home.