In this 1993 moment, he wore a white t-shirt, layered under a black crew neck sweater that was loosely draped over straight cut indigo jeans. Finished with minimalist accessories (shoutout to the wallet chain), the result was an easy style win that can lend itself to any age and season.
If your style revolves around tailoring, a change in sartorial texture is key to battling the biting temperatures ahead. The best one, according to DiCaprio: velvet, as demonstrated by this excellent head-to-toe black ensemble he sported during Milan Fashion Week.
Pictured here at Hollywood’s most noteworthy event — the annual Academy Awards — the actor opted for a single-breasted style, designed with satin peak lapels and a soft shoulder line to bring out the broadest part of his silhouette.