Photo Report: A WindUp Weekend In Chicago

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This past weekend, brands and watch enthusiasts alike descended upon Chicago’s West Loop area for the annual edition of the WindUp Watch Fair. The event is put on by our friends at Worn & Wound and joins the year’s programming alongside fairs in San Francisco and New York. And, despite a seriously hot weekend in Chicago, attendance at the fair was huge as folks traveled from far and wide to check out the latest from a wide variety of brands, including Oris, Zodiac, Brew, Citizen, AnOrdain, Monta, Christopher Ward, Oak & Oscar, Lorier, Fortis, and many many more. 

This is my second year attending WindUp Chicago in connection with my plucky side hustle of a podcast, The Grey NATO. I was joined by my co-host – author, and Hodinkee Alum – Jason Heaton, for some podcasting with the folks from Worn & Wound and a seriously fun hangout with Citizen. As always, I brought along a camera, and the following covers a cross-section of what I got to see and handle at the show. From vintage divers to brand-new GMTs and about as many lume dials as I could find, it’s quite the mix, but don’t scroll so quickly that you miss a certain modded Tudor below. 

Collective Horology’s collaboration with Armin Strom, the titanium-cased P.03. 

WindUp is a great event with a chill and casual vibe that I really appreciate. Attendees are there to see and buy watches, but a lot of the show is like any great watch meetup, offering the chance to swap watches and chat with like-minded friends. For those who want to check out a WindUp for themselves, the NYC fair will run Friday to Sunday, October 20-22, and you can find more information here. Otherwise, a huge thanks to everyone who came to hang out in Chicago; it was a blast.  

Lume dials! My JDM Aqualand 2007-17W next to the brutish Citizen Promaster Dive BN0227-25X. 

Always a treat to see an IWC 3711 Doppelchrono. 

A PO1 that has been relieved of the model’s distinctive bezel locking system. 

A wild Doxa appears. 

A Montblanc 1858 Geosphere in bronze with a nicely matched camera. 

The newly released Benrus Ultra-Deep. 

A Tudor Pelagos FXD. 

A very cool Citizen Jump Hour Independent 1481010. 

Raven watches with their collection on display. 

Part of the fun of owning an Aqualand is letting others try it on. It’s the smallest-wearing big watch I’ve ever come across.

The upcoming Nodus Canyon, a watch made in collaboration with Matt Farah of The Smoking Tire. 

Jim Wirth of Giant Mouse Knives rocking a seriously bright Zenith diver. 

Even brighter under the light of a UV torch. 

One seriously weathered Citizen 800M Professional Diver. 

The brand new Lorier Hyrda, a 9075-equipped flyer GMT in a 41mm case that retails for $599. More on this very soon. 

Sinn was strongly represented. 

The latest Farer Endeavour Aqua Compressor in titanium. 

Nice to see strap-maker David Lane Design with a booth at the show (the brand has produced straps for the Hodinkee Shop in the past).  

Worn & Wound’s own Blake Buettner rocking a Ploprof. 

An incredible vintage Aquastar Model 60…

With a special engraving for all you Sealab fans. 

Not one but two Breitling Datoras…

This one felt brand new. 

And still had it’s original case back sticker. 

​Hodinkee 

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