As Watches & Wonders approaches, the conversation around what Rolex might do next starts to heat up, and last year, one model had people divided: the Rolex Land-Dweller. In this episode of On Time, Lex Borrero sits down with car and watch collector Sean O’Neill to break down the design language behind some of today’s most talked-about watches, Seans personal watch and car collection, and why pieces like the Land-Dweller spark so much conversation in the first place. From cars to architecture, they explore how taste is developed, how nostalgia plays a role in what we choose to wear, and why some collectors are drawn to pieces that go against the grain. Along the way, they speculate on what Rolex could do next, from potential updates to the Land-Dweller to the possibility of new colors in 2026. New episodes of On Time drop every Thursday at 7:30PM EST! #watches #rolex #WATCHESANDWONDERS2026