Watch buying challenge: The best watches of Windup New York 2025

Time+Tide

The best do-it-all watch, the best dress watch, the best dive watch, the best value proposition watch, the best pilot’s watch, the best watch of the fair (the one watch, if we could only choose one) that they would each want to walk away with… That is the challenge Andrew and Zach set out on for the 10th edition of Worn & Wound’s Windup New York watch fair. With 150+ exhibitors in attendance, Andrew and Zach had a lot of options to choose from.

But you’ll have to watch the full video to see their selections, and be sure to leave a comment with your votes per category, so we can see who the winner is of Andrew versus Zach, Windup New York watch buying challenge round 2. And if you enjoy this video, be sure to go back and check out round 1 from last year.

What is Worn & Wound Windup Watch Fair?

“Ten years ago, Worn & Wound launched the Windup Watch Fair with a simple goal: to bring watch enthusiasts together in a fun, approachable setting,” Worn & Wound explains. “A decade later, it has become the largest watch event in the world, connecting collectors, newcomers, and brands in a vibrant, community-focused space. In celebration of our 10th anniversary, we’re thrilled to announce four fairs planned across the country in 2025—including a brand-new stop in Dallas. This milestone year promises to be our biggest and best yet.”

The NYC edition of the 2024 Windup Watch Fair was, without a doubt, the biggest watch fair in the world… until this year’s edition arrived! With well over 140 brands in attendance in 2024, over 150 in 2025, and over 10,000 watch enthusiasts in the NYC area lining up to head through the doors and explore, Windup has become a must-visit event each October in New York City for watch geeks. However, this travelling watch fair is also held in other locations each year, travelling to Dallas (March), San Francisco (May), and Chicago (July) as well.