Ralph Lauren Polo Bear Tuxedo 42 mm

"I have always loved contradiction, blending a tuxedo jacket with a pair of jeans and boots.” Ralph Lauren’s distinct combination of a double-breasted dinner jacket with denim and steel-tipped boots—a look he has reinterpreted for formal occasions across decades of his career, most recently for his 50th Anniversary celebration in New York City—is embodied in the style of Tuxedo Bear. The watch is completed with a black alligator strap.

The Polo Bear debuted in 1991 as 200 limited-edition bears produced by Steiff, the famed German toy manufacturer, and dressed in miniaturized Polo Ralph Lauren apparel. In the years since, this stylish bear has appeared as embroidery, prints, and patches on a variety of items, from neckties to sweaters.