After the seemingly never ending hype around steel sports watches, dress watches have been making a comeback. But it’s not just the average 42 mm dress watch that’s sparking interest (although, those too, are in the running), but also funky vintage diamond-accented timepieces or small-sized, almost feminine pieces are trending. Recently, actor Paul Mescal was spotted on the red carpet of the Annual Academy Museum Gala wearing a Cartier Tank Mini with his tux, while sports legend Dwayne Wade wore a 28 mm diamond Tiffany & Co. Eternity watch with his black tie ensemble to the same event. While these guys were wearing dress watches in their intended setting, here we show you how to make a dress watch work for casual weekend wear too.

Try dabbling in unexpected pairings like an army green Ghiaia safari jacket with a vintage Chopard Happy Diamonds timepiece or Breguet Classique Ref. 7147 (the ultimate dressy timekeeper) with a Louis Vuitton sweatsuit and a Brioni overcoat. Anything goes these days and the more unexpected the timepiece, the stronger the statement. It’s good news all around—for your wardrobe and your investments in the vault.

Jaeger-LeCoultre 40 mm Reverso One Duetto Jewellery in 18-karat pink gold and diamonds, $49,900. Opposite page: Chopard 32 mm vintage Happy Diamonds in 18-karat white gold and diamonds, $12,500, analogshift.com; Ghiaia cotton safari jacket, $895; Eton cotton T-shirt, $225; Hermès denim trousers, $1,050.

Audemars Piguet 34 mm vintage automatic ultrathin watch in 18-karat white gold and diamonds, $9,300, classicwatchny.com. Opposite page: Cartier 41.4 mm Tortue in platinum, $35,600, limited to 200; Gabriela Hearst hand-knit cashmere sweater, $2,500; Officine Générale cotton-poplin shirt, $315.

Breguet 40 mm Classique Ref. 7147 in 18-karat white gold, $23,500; Brioni wool and cashmere overcoat, $8,300, and silk knit crewneck sweater, $1,395; Louis Vuitton wool track pants, $1,330, and wool hooded jacket, $3,150. Opposite page: Patek Philippe 39 mm Calatrava Ref. 6119R-001 in 18-karat rose gold, $33,110.

Piaget 45 mm Andy Warhol in 18-karat rose gold, $43,400. Opposite page: Rolex 29 mm vintage King Midas Ref. 4342 in 18-karat yellow gold, $17,750, classicwatchny.com; Brunello Cucinelli denim shirt, $995; Tom Ford cotton chinos, $790; Berluti leather belt, $710.

Model: Arthur Sales
Grooming: Amanda Wilson
Senior market editor and casting: Luis Campuzano
Photo director: Irene Opezzo
Photo assistant: Alejandro Suarez
Prop stylist: Elizabeth Derwin