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Tuesday, November 3, 2026 | 3:38 PM

James Stacey and Tim Jeffreys Go Head-to-Head in the Ultimate Windup Watch Fair Shopping Challenge

The Windup Watch Fair has firmly established itself as an unmissable cornerstone of New York Watch Week, evolving into one of the most vibrant and heavily attended gatherings on the city’s horological calendar. Each year, the event successfully draws thousands of passionate watch enthusiasts, curious newcomers, industry insiders, and dedicated collectors from around the globe into a shared space celebrating all things timekeeping.

Just Because: How To Spend $250 At Windup New York

Marking its impressive eleventh edition, the fair has continued to expand its footprint and influence within the broader watch community. This year’s milestone event featured more than 160 distinct brands participating on the floor, ranging from beloved independent microbrands and creative startups to globally recognized heritage manufacturers. Major industry favorites such as Baltic, Brew, Sinn, and Oris were among the prominent names showcasing their latest innovations, timeless designs, and highly anticipated releases to the eager public.

The 2026 iteration of the Windup Watch Fair marked its third consecutive year hosted at Center415, a spacious and dynamic venue situated right on Fifth Avenue in the heart of Manhattan. Once again, the location provided the ideal backdrop for visitors to deeply engage with the horological community. The venue layout gave attendees the rare, hands-on opportunity to interact directly with brand founders, master watchmakers, and company representatives, allowing them to examine, try on, and shop from an eclectic mix of independent creators and established luxury houses alike.

Just Because: How To Spend $250 At Windup New York

Beyond traditional watchmakers, the exhibition floor also embraced a wider lifestyle aesthetic by welcoming a curated selection of tech innovators, outdoor gear manufacturers, and specialty travel brands. Among these complementary exhibitors was Ad Patina, a dedicated fan-favorite vendor known for offering a fascinating slice of horological history through vintage print advertisements sourced from iconic watchmakers of decades past. This diverse mix of vendors ensured that there was something to capture the imagination of every visitor, regardless of their specific collecting niche or budget.

One of the most defining characteristics of the Windup Watch Fair—and a primary driver of its massive popularity—is its commitment to accessibility. With free admission open to the general public, the fair removes the financial and social barriers that often intimidate newcomers entering the traditional luxury watch space. It offers a welcoming environment where veteran collectors with multi-thousand-dollar portfolios can rub shoulders with students and novices who are just discovering their appreciation for mechanical timepieces. This inclusive atmosphere has rightfully earned Windup its reputation as the world’s largest public watch fair, fostering a community-driven spirit that celebrates horology for everyone.

Just Because: How To Spend $250 At Windup New York

Naturally, attending an exhibition of this scale and magnitude is an exciting prospect for any watch publication, but this year, the editorial team decided to elevate the experience by introducing a playful element of friendly competition. To put their resourcefulness, taste, and horological savvy to the test, Editor-in-Chief James Stacey and Deputy Editor Tim Jeffreys squared off in a head-to-head shopping challenge. Armed with an identical, strictly limited budget of just $250 each, the two editors were let loose on the bustling exhibition floor with a singular mission: to find out who could make the absolute most of their money before time ran out.

Navigating a convention floor packed with hundreds of tables featuring everything from high-end timepieces and precision-engineered mechanical movements to premium leather watch straps, specialized tools, fun tech gadgets, and unique memorabilia is no easy task. With a modest $250 cap, both editors had to carefully weigh their options, exercise strict financial discipline, and make strategic choices about what truly represented the best value and style at the fair. Should they pool their funds into a single, highly affordable entry-level accessory, or spread out their spending across multiple smaller items? The pressure was entirely on.

Just Because: How To Spend $250 At Windup New York

The resulting showdown captured the essence of what makes attending watch fairs so enjoyable—the thrill of the hunt, the appreciation for thoughtful design, and the camaraderie found among people who simply love watches. Watch enthusiasts and readers can now view the full video chronicling James and Tim’s shopping sprees, observing their decision-making processes, debates, and final purchases as they scour the crowded aisles of Center415. Once viewers have had a chance to evaluate the respective hauls, the editorial team has invited the community to weigh in, leaving comments to declare whose shopping strategy ultimately reigned supreme. The challenge was expertly captured, produced, and edited by video producer Erika Kondo.

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