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Worn Out Wednesday – Winston Fisher

By Cator Sparks Published December 21, 2019

Today we speak to Winston Fisher, of Fisher Brothers Realty and Drill Fitness.

I was born and raised in New York City. I have always had two passions – real estate and being active.

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I pursued my passion for real estate by joining my family business, Fisher Brothers. As to my other passion, over the years I have gone on numerous adventure trips, hiked Mt. Kilimanjaro and Machu Picchu, did mountain bike tours in Utah and California, signed-up for various endurance races and triathlons.

In June 2014, I was part of an eight man team participating in RAAM (Race Across America). We were Team Intrepid Fallen Heroes, riding not just to accomplish an incredibly challenging physical feat, but to support wounded US troops. We accomplished our goal of completing the race in just 6 days! We dedicated our race to support Iraq and Afghanistan veterans suffering the terrible effects of traumatic brain injury (TBI). In June 2015, I will be doing RAAM again, but this time Team Intrepid Fallen Heroes will be a four person team.

I started Drill, because I wanted to bring my passion and intensity for working out to a studio. I believe there is a market for something that is cool, clean, modern, fun and hard. Drill reflects my love of pushing yourself to the extreme in a teamwork environment.

As for my personal style:

Jeans: Ron Herman

Shirts: John Varvatos and Rag & Bone

Pants: Zegna

Suits: Zegna

Shoes: Zegna and Fiorentini Baker

Accessories: Todd’s bracelet and an Evolution necklace my girlfriend gave me.

Outerwear: Patagonia & John Varvatos

Favorite Cologne: Hate it. I just go with the fresh scent left after a shower.

Your favorite App: Postmates

Favorite piece of technology: Wahoo Kickr

Next tech purchase: maybe Curved 3D TV

Former Former Digital Trends Contributor, The Manual

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Shinola has made watches about Detroit, about the Apollo program, and about a lake monster. Its newest one is about a sailboat race, and damn, is it good-looking.

The Detroit-based brand is launching the Mackinac Night Race, a limited edition built around the yacht timer — the countdown complication used to time the start of a sailing race, aka one of watchmaking's more specialized tricks. The name nods to the Great Lakes maritime history the watch draws on (so not technically an official race tie-in).

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One of the most iconic ways a man can stand out is to make a statement with his style. Now, this isn't as easy as it sounds. Most of the time, if a man doesn't know what he is doing when he goes to make a statement, he goes overboard. Colors, patterns, textures, they can all work together or battle each other out for attention and cause problems. For instance, wearing a bright color combined with a crazy pattern can make you look more like an optical illusion than a stylish man. You look like you are cosplaying The Joker instead of methodically piecing together pieces that are working together to give an outfit depth. One of the tricks I have always loved to incorporate with my looks is a statement shoe. A typical everyday outfit can be elevated easily with a shoe standing out with color or pattern. One of my favorite brands to go to when I want to do that is TAFT. They are the best in the game for a statement shoe, and their new edit is a way to capitalize on that idea.

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Windup Chicago proves the watch fair is still the best room in the business

Five years in, Worn & Wound's traveling show packed a new venue with everything from solo microbrands to Swiss tourbillons, with prices ranging from $250 to $29,000.

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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.