Plenty of watch events would strike any reasonable observer as “just fine.” Windup Chicago, on the other hand, cleared that bar before I got to the first table. The roving fair, which ran July 10 through 12 at Morgan MFG in Chicago, is back for its fifth year in the city overall. It’s the third Windup of 2026, after Dallas and a San Francisco show that pulled 7,000 people over three days.
Admission was free, as it has been since Worn & Wound started running these. With lead sponsors like Atelier Wen, Christopher Ward, Citizen, eBay Live, and Oris, there was plenty of heft, but also, there were panels, podcast recordings, and a Bruichladdich tasting for anyone who needed a break from squinting at dials.
What stuck with me was the spread: in one room, I handled both a $250 chronograph and a $29,000 hand-finished dial, and the guys selling them were standing right there.
Chinese ascendancy, courtesy Atelier Wen
One of the best conversations I had all weekend was with Robin Tallendier, co-founder of Atelier Wen, who was working his own booth like everyone else.
Wen came to Windup Chicago as a lead sponsor, which is a strange place for a brand that started eight years ago selling a $500 watch and getting told they were out of their minds for it.
The brand’s line now runs a bit more upscale, deliberately. The Perception sits at the entry point around $4,800. The Ancestra lands near $5,850. Then there’s the Inflection at roughly $29,000 — the hand-finished piece I got on my wrist, and the reason I stood at that booth for twenty minutes.
Tallendier told me the plan is to fill in more references at both the entry point and the top before working toward the middle, possibly with a complication like a chronograph.
Wen is a French brand built around Chinese craftsmanship — they considered a Chinese name, decided it wasn’t honest given that they’re two French guys, and picked something that lives in the middle. Tallendier’s read is that the brand will always be a Western take on Chinese watchmaking, and pretending otherwise would be a worse product.
The market’s moved with them. He credits the shift to categories that aren’t watches at all — Chinese consumer electronics and EVs doing the heavy lifting on perception, and watches riding the wake. Eight years ago a $500 Chinese watch was sketchy. Now the entry piece is ten times that and nobody blinks.
Their biggest market is the US, which surprised him. His theory: Americans will hear you out and judge the watch. Texas, of all places, turned out to be a real pocket of customers. Who knew.
Great decisions, small booths
Two rows back from the banners, the boutique brands were making their case in two directions at once. Some are betting on doing something technically strange that a bigger company would never sign off on. Others are betting they can undercut everyone by an order of magnitude. Both bets were paying off in the same room.
Horage Autark Tourbillon
Horage builds its own movements in Biel, which is a declaration that most brands this size cannot hope to make. The Autark pairs a micro-rotor with a flying tourbillon in one in-house caliber, the K-TMR — a combination that, per Horage, usually starts north of 40,000 Swiss francs, and climbs into six figures.
Meanwhile, the Autark starts at roughly $16,000 at current rates. The case and integrated bracelet are Grade 5 titanium, under 9mm thick, and the thing is startlingly light for a watch with that much going on inside it. There’s a 72-hour power reserve, and the tourbillon cage weighs 0.29 grams.
MeisterSinger Neo
MeisterSinger isn’t a microbrand — it’s a German outfit that’s been at this since 2001 — but it’s one of very few brands making single-hand watches with any conviction.
The Neo is the pure version: one hand, a track marked in five-minute increments, and the understanding that you’re going to be approximate about it. Reading it takes about four seconds the first time and roughly zero the tenth. Worth putting on if you’ve only ever seen one in photos, worth taking home if you don’t mind the roughly $2,000+ price tag.
DeMarco Chronograph
Michael DeMarco runs this brand out of Boston, and the show-exclusive price was $250 — against a $329 list, which the card on the table was happy to tell you. For that you get 316L stainless, a Seiko VK64 mecaquartz, curved sapphire, a 120-click bezel, and three quick-release straps in the box. Pretty good deal, overall, with some bold colorways: pistachio, salmon, ice blue, a purple that has no business being that snazzy. I’ve seen worse specs at four times the money.
Breda Pulse Locket (Chicago Version)
This weird little guy was made specifically for the fair, with a rectangular steel case and the city’s name engraved across the face. That doesn’t detract from the small sub-dial low, visible while the front panel is closed (or popped open like a locket). It’s the kind of unique design decision that is doable on a $270 watch — and it won’t break the bank.
History for sale
For everything new at Windup, the busiest corner of the room belonged to people selling watches older than the fair itself.
The Watch Preserve was the only vintage dealer on the floor, and it showed — this was their second year in Chicago, and the dealer running the booth told me the crowd around it never really thinned out. Their pitch isn’t trophy pieces. It’s introducing newer buyers to vintage through stuff that’s quirky, accessible, and fun to wear rather than precious.
Vintage Omega and vintage Cartier both move fast — they’d brought nine Omegas and were down to three, and both Cartiers sold before I got there. Anything genuinely interesting under $500 is a reliable seller too, and a good chunk of their case was American-made pieces from the same era.
A few booths over, Duckworth Prestex was doing a version of the same thing from the other direction — not selling the past, but rebuilding it. The brand’s reissues are modeled directly on watches Neil Duckworth’s grandfather made, and it shows in the case: a rectangular cushion shape with a screw-down crown that reads as pure 1930s.
They had the real thing on display next to the new watches — an original 1935 Prestex, the piece the whole line is working from — so you could look at both at once and see exactly how little had been changed.
The IRL advantage
I didn’t make it to Christopher Ward’s booth — they were slammed the whole time I was there, which is its own kind of data point. Between that and the line at eBay Live’s setup, running a livestream auction off the show floor, it was clear the fair isn’t just competing with itself year over year. It’s competing with everyone’s phone.
But that’s just the thing: going in person is exactly the kind of hands-on opportunity any watch enthusiast will dig. Where else are you going to try on watches like the Inflection and the Autark, sitting two booths down from a guy selling $250 chronographs, all of them getting the same amount of attention from the same crowd?
