Fashion / Style

Our favourite 90s and early 2000s looks from Leonardo DiCaprio

Leonardo DiCaprio style

Mark your calendars ladies and gentlemen! It's that time of year again: Leo season... no, not that one. It's the other one – that's right, we are only a few days out from 11 November, the 49th birthday of the one and only Leonardo DiCaprio.

DiCaprio's storied career in Hollywood is trumped by just about no one. Since his days as a teen heartthrob in the 90s, to his Oscar-worthy (and finally, Oscar-winning) performances in some of the greatest films of the last two decades – he's nothing if not a household name.

The iconic characters he's portrayed have been burnt into our minds – from the Hawaiian shirt he donned as Romeo in Baz Luhrmann's adaptation of the classic Shakespeare tale, to the sleazy, suited portrayal of Wall Street's own Jordan Belfort. Who could forget his take on the great Jay Gatsby himself? Or his role as an undercover cop in Scorsese's The Departed.

But if there's one thing more iconic than his characters' style, it's a young Leonardo DiCaprio's street style. The actor has always kept things casual, lighthearted and neutral-toned when it comes to his street style and red carpet looks – he knows he doesn't need to be flashy. He's a long-time fan of the classic baseball cap, and is – relatably, but perhaps surprisingly – a fan of an Ugg boot moment too.

Below, we take a look at some of our favourite style moments from Leonardo DiCaprio.


An early adopter of the belt chain.


A young Leo was a big fan of the classic baseball cap.


Knitted beanies also made up a large proponent of his wardrobe.


Loving this poolside look.


This chocolate brown suit is a favourite.


Uggs will never not be a part of the perfect early-morning servo run fit.


This oversized fit with backwards baseball cap just screams 90s.


The knitted beanie comes back into play here.


And again... in a new colour way.


Once again favouring a neutral palette of dark browns on the red carpet.


Showing off his athletic side.


Graduating to the pinstripe suits and silk shirts.


This style of brown leather jacket has really seen a resurgence in popularity again recently.


Not sure what the inspiration behind this look was – but somehow, it works.


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Images: one, two, three.