Two Hodinkee editors spend $250 each at the 2026 Windup Watch Fair in New York

Editor-in-Chief James Stacey and Deputy Editor Tim Jeffreys each set out to make the most of a $250 budget among watches, straps, gadgets and more at the eleventh Windup Watch Fair. Watch for how each weighs their choices at a show with more than 160 brands, then decide whose haul is better.