In 1996 the world took a collective break from whatever the hell it was doing as we all simultaneously drooled over Leonard DiCaprio in Baz Luhrmann's hyperactive, rave-inspired film adaptation of Romeo and Juliet. The death of River Phoenix less than three years earlier had left a vacancy in the global culture department for a reticent bad boy with an angelic face, and Leo stepped in to fill that void. His waifish appearance meant there was always something a little androgynous about his look and he was never afraid to reveal his chest or opt for some hip-hugging jeans. That lean frame allowed him to pull off a variety of looks.
Whether it was a brightly colored blazer over a billowing silk shirt with a loud print or an over-sized black button up with some sleek shades, dark denim and sneakers, Leo looked good in it all. There was always more than enough hair product to go around. But he never seemed to be trying too hard, and it seemed like he was casually throwing on whatever he picked up off the floor of his bedroom five minutes before he left in the morning. Unfortunately, Leo's look had the longevity of everything else in the '90s (i.e. the granola fad, beanie babies), but we can look back with fondness, and of course, try our best to cop the look.