November 11, 2014 marks Leonardo DiCaprio’s 40th birthday, and because we didn’t know what to buy him, we made him this: a complete retrospective of his evolving fashion choices.
And what a long, strange trip it’s been. From whatever happened in the '90s to the cargo shorts free-for-all of the last four years, our Leo has refused to commit to a specific aesthetic, and as such, has confused and fascinated us all. Let’s re-visit it. Why? Because a real man makes his own luck. Meet us at the clock.
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The man loves hats, what can we tell you. But even though this look may not have much on the chapeaus of the 2010s, Leo redeemed himself with a beaded necklace, layers, and a button-up we would still gladly purchase from Value Village now and incorporate into our own wardrobes respectively. (Sadly, Leo dropped that necklace into the ocean after this photo was taken for dramatic effect.)
Well let us say what we’re already thinking: give us that coat. Seriously. Back in 1990—and thanks to the "Parenthood" costume department—the boy embodied 2014’s fall/winter style perfectly. (Walk into any store and you will see denim button-ups and camouflage coats, we promise you. And if not, walk out.) Even as a teen, he had his eye on the prize. And by “prize” we absolutely mean, “trendy pieces you can find in most seasonal collections.”
Do you like denim? Good. Do you like oversize denim? Excellent. Still layering like a champion, Leo evolved from both his former haircut and affinity for hats to embrace the grown-out brush-cut most of us saw worn by our grade school peers. He also kept the necklace, which, upon second glance, is paired with velvet. Meaning that Leo’s style credibility may have started much earlier than any of us thought.
You may think, “There's a lot happening here, and yet it's all working, so Leonardo DiCaprio may be a warlock.” True. How else do you explain the combination of corduroy, a belt, a knit vest, a t-shirt, and jean to translate? Usually, it’d be a fashion nightmare. Instead, it just looks like an homage to late ‘70s trends.
At the "Reality Bites" premiere, Leo opted to look “the most nineties possible” which is a gift both to us and the film he was honoring. Wearing a suit that not even vintage-in-2014 can redeem, the young DiCaprio paid homage to the ring bearers and prom attendees across North America, who were also forced to wear overly baggy pants, an ill-fitting jacket, and a very loose button-up. Solidarity.
Shout-out to the Tiger Beat poster all of us hung in our rooms so we could pretend to be Claire Danes. Frankly, it’s impossible to look at this photo of Leo at the "Romeo + Juliet" premiere and not return to the “But how do I meet and marry him?!” mindset that ruled 1996-1998, respectively. It didn’t matter that his love of lapels would rival our own, or that the mid-nineties called for the largest cut of suits possible. This was real. This was love. This was a flashback—we're so sorry, guys.
The premiere of "Titanic." Or: the day a lot of us saw Leonardo DiCaprio’s not-Jack hair for the first time. A harrowing experience exacerbated only by the fact that he opted for (another) velvet suit. (Or at least velvet-ish.) The good news: it fit better. The bad news: that tie somehow scored an invite. Never let go.
So what did the four years between "Titanic" and this photo bring? Nothing special. But, as Leo began taking a step back in the early 2000s, his fashion went from L.A. nightclub chic to “kind of what we see Leo wear now.” Look: baggy pants, running shoes, an Adidas hat, and a t-shirt. And this is to a bar. Did Leonardo DiCaprio pioneer normcore and/or dad-fashion? We can only dream. (And we do.)
It’s official: Leonardo DiCaprio never really emerged from the turn of the century. Here, at a 2002 speech on climate change, the artist-formerly-known-as-Romeo is in simple black dress pants, a black button-up, and a goatee that he still kind of has now. This is the real deal, people: this could’ve easily have happened in 2014. At some point, in 2001 (and/or 2002), Leo said, “This is how I dress now.” And his life has only really gotten better because of it.
See? That is the face of a happy man. And who can blame him? Reunited with his jeans, his hat, and his facial hair, Leonardo DiCaprio chose comfort over a decade ago and has never looked back. We cannot say the same. Leo, please return our calls.