For all the talk about shrinking watch sizes, the industry still has a rather generous definition of “small.” At New York’s Windup Watch Fair, held October 16–18 on Fifth Avenue, more than 160 brands gathered to show off their latest creations. We went looking for the pieces that might appeal to collectors of smaller watches, and found everything from a remarkably elegant rectangular dress watch to a surprisingly persuasive military revival.

Our favorite was the Capri from Dutch independent DE RIJKE & CO., which has just joined the brand’s permanent collection in three exquisite colorways: champagne, salmon, and silver. Measuring 28.5 by 38mm and just 6.5mm thick, it pairs a curved sapphire crystal with frosted dials and a hand-wound La Joux-Perret movement. The result feels both vintage and rather modern, without trying too hard to be either.

Bulova brought some history to the proceedings with its A-11 Jimmy, a 37mm automatic field watch inspired by a World War II-era model. Developed in connection with the upcoming film Jimmy, about actor and pilot Jimmy Stewart, it has a black dial, highly legible white markers, and a beige nylon strap. Not traditionally feminine, certainly, but a compelling choice for anyone who appreciates the history of the wristwatch and its rapid development during the two World Wars.

Brew went in an entirely different direction with its Metric Chrono Taxi. The 36mm chronograph sports a yellow-and-black dial inspired by New York’s ubiquitous cabs. Limited to 1,000 pieces and priced at $495, it’s cheerfully literal and, frankly, pretty irresistible.

If these releases suggest anything, it’s that the watch world isn’t fully committed, yet, to the daintiest silhouettes. Tiny watches have become something of a red-carpet staple in recent years, but the trend remains largely confined to the high-jewelry world, with independent watchmakers still relatively slow to embrace truly petite proportions.