By Matthew Sebra for GQ.
We look back at the leading man's stylish progression from kid actor to A-lister.
1989
Despite looking damn sharp in a suit, at heart DiCaprio is an American kid who prefers the basics when off duty. Of course, even as a kid TV actor, his basics were anything but that, like this Nike varsity jacket that predates menswear's collective obsession with the outerwear piece by about twenty years.
1989
Another look Leo anticipated at an early age? The Chandler Bing/Charlie Sheen bowling shirt. For the record, we're less enthusiastic about this one.
1993
The '90s played host to countless bad trends, and not even DiCaprio could escape the prevalence of shallow knit skullcaps. Because why wouldn't a guy want to wear a hacky sack on his head?
1993
DiCaprio turned Hollywood's heads with his performance in What's Eating Gilbert Grape?, but at the film's premiere, he's making us scratch ours as we try to figure out this layered mash-up.
1994
Yet another instance of DiCaprio as a menswear prophet, wearing a getup remarkably similar those just shown at Prada's Fall 2013 runway. Mark Wahlberg, on the other hand, is clearly regressing to a Fat Albert phase.
1994
Leo wears what basically every '90s teen did to his prom to his first Golden Globes, at a time when black tie meant no tie at all.
Read more: David Beckham's 25 Most Stylish Looks
1994
Every man must find his stylish path in life and that usually involves some unfortunate detours. In DiCaprio's case, it's this velvet shirt.
1996
Believe it or not, in 1996 this look at the Romeo & Juliet premiere was about as of the moment as you could be, four-button front jacket included.
1997
For the premiere of DiCaprio's career-changing Titanic, the actor suits up and basically lays the sartorial groundwork for the next fifteen years of red carpet appearances, including that over-buttoned-up jacket front.
1998
DiCaprio' second Globes appearance was an improvement over his first outing (note an actual bow tie), but the actor still had yet to learn what a real formalwear lapel looks like.
2002
At the Gangs of New York world premiere we get our first glimpse of adult Leo. Notice the gelled spikes and hanging tendrils of his youth are slicked back for a leading man look that aligns with his more mature movie roles.
2002
Later that year the actor tries his hand with some rare (for him) bold blue color at the Catch Me If You Can premiere.
2004
As an adult, DiCaprio has a uniform off the red carpet, and to this day the actor sticks to it: backwards ball cap, button-down, and dad jeans.
2005
Back at the Golden Globes, the actor finally nails eveningwear in one sharp peak-lapel jacket, but pairs it with a bib-sized silk tie. His Aviator nomination ticks off a series of red carpet appearances for which the actor gets schooled in the ways of black tie dressing...
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