When Timepieces Get Whimsical: The Most Playful Watches Right Now

December 5, 2025

By Joshua Hendren

9 min read

Watchmaking isn’t typically known for its sense of humour, we are more used to functional designs, artful dials, complications, and jewelled designs. Usually, we wear watches to tell the time but lately, a handful of brands have started to cater for another need – to stand out and showcase one’s personality through accessories that they wear. To answer this need, watchmakers are showing a lighter side, creating timepieces that wink, grin or simply refuse to take themselves too seriously.

The world of horology has always valued creativity, but recently, that inventiveness has taken a new turn. Brands are finding ways to inject wit into some of their most complex timepieces, not through gimmicks, but through clever design details and unexpected animations. The result is a growing category of playful watches that mix craftsmanship with character to offer collectors something unconventional and light-hearted, with a touch of humour or even nostalgia. Here, we round up some of our favourites.

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In the continuation of this article:

  • Playfulness is becoming a design language in modern watchmaking.
  • Complications are being reimagined not only for performance, but for personality and charm.
  • From animated dials to character‑driven mechanics, these watches prove that humour and high craft can coexist on the wrist.

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