Getty Images / Rose Hartman

The ’90s were quite the time to be alive. And not just because they introduced us to one of the biggest heartthrobs in Hollywood — Leonardo DiCaprio — and delivered a bunch of awesome fashion trends that are still hot today. No, the ’90s gave us the greatest streetwear brands, FriendsSeinfeld, countless awesome cartoons, and so much good hip-hop, it had to be given a name.

Despite all that, we’re still heavy on Leo and his style. And when those worlds collide, it’s a truly great thing. So, in honor of that fact, we’ve collated a range of Leo’s best looks from the ’90s, including iconic ‘fits from Romeo + Juliet, and that time he held a swan for no good reason, and laid them all out for you alongside tips to help you recreate Leo’s’90s look now.

1. Hawaiian Print

One cannot talk about the relevance of Leo’s ’90s sartorial presence without beginning with the various shirts he donned in Baz Luhrmann’s Romeo + Juliet. The most iconic, of course, are the two printed Hawaiian short sleeves, both in a bright royal blue and featuring red, pink, and yellow floral prints.

The shirts are perfect for those who frequent any vintage store — not only those in Hawaii and Verona Beach (or just Verona, if you’re more keen on sticking to Shakespeare’s OG location).

Of course, the vibe is much more omnipresent than one reference to Leo and this 1996 movie. Over the two plus decades since its debut, the retro print button-ups have been clocked everywhere from Saint Laurent runways, to Gucci, and Louis Vuitton, and on the backs of style kings like Tyler, The Creator, Kendrick Lamar, and Donald Glover.

If you’re looking to cop, we’ve selected 10 of the best Hawaiian shirts for you to build your Romeo + Juliet ’fit around.

2. Tartan Trousers

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daily basis #90s #leonardodicaprio #nostalgia

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While many of you might want to keep your tartan trousers in an Avril-Lavinge-circa-2000-shaped box, you’d be doing yourself a serious disservice. Although not many designers have opted to include the Scottish-native pattern in collections of late, there’s one British design house on whom you can always rely to serve up checkered delights: Burberry.

While the label’s nova check may carry a rocky history, gone are the less than luxe associations — particularly in thanks to Christopher BaileyGosha Rubchinskiy, and Riccardo Tisci, who just unveiled a reimagining of the traditional formation in the SS19 show.

Unsure how to style your nova? Here’s how attendees of Burberry’s show flexed theirs.

3. Oversized Knits

When Leo rocked these oversized chunky knits in the ’90s, larger-than life-pullovers were still associated the burgeoning grunge scene in the Pacific Northwest.

Decades later, that is no longer the case. Now, when it comes to knitwear, the bigger the better, because being comfortable and being stylish are now one and the same. Leo knew this, which basically means he was way ahead of his time.

Of course, championing the oversized look doesn’t mean you can just chuck on any old body-engulfing thing. Nor does it mean you should make like Balenciaga and throw every large item you own on at once.

Luckily, there are plenty of roomy knits around to keep you snug as a bug in the most high-stylin’ of rugs — and not all of them will break the bank.

4. Performance Sunglasses

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In case you missed the memo, let ’90s Leo deliver it for you: Sports sunglasses look to continue their reign well into SS19. In July’s resort shows, they were literally everywhere, clocked at presentations from Prada and Kenzo, to Heron Preston and CMMN SWDN.

Boasting polarized lenses in hardy industrial frames, these futuristic face treats — once reserved for NASCAR dads and pro-cyclists — are the accessory trend you’re going to want to get involved with come next summer. And who better to show you how to wear them than babyfaced Leo. You too could wear these bad boys while casually practicing your yoga lotus position in a cardboard box and still look fierce.

One cannot talk about sports sunglasses, however, without including Oakley — the brand big in the active eyewear game in the ’90s, and still running the show now. In fact, the brand is pretty much responsible for the trend’s comeback. Read up on how it did so, and the frames you should cop, here.

5. Relaxed tailoring

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Boogay woogayyy

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It’s not easy for a young dude to don a slightly-oversized suit and not look like they’ve stumbled into their father’s wardrobe (and then promptly fallen out of it ). And that was especially difficult to achieve in the ’90s, when the likes of Chandler Bing and his bad tie/clashing sweater-vest game was dominating screen time, and spreading the message to countless men that this was an acceptable way to dress.

Here, however, Leo demonstrates how to wear a casual suit and not look super awkward. Firstly, he’s kept the color neutral, opting for a dark blue suit with a faint pinstripe detail that gives off a corduroy effect. Secondly, he’s played with traditional suit-staples, throwing the idea of a tie and shirt collar in the trash, and giving off a much more youthful vibe as a side effect.

Need more tailoring inspo? Check out all the blazers we spotted at Milan Fashion Week.

6. Don’t underestimate the power of a good prop

If you really want to flex with the best of them, creating fire IG content that your followers “need” in their daily lives, you’ve got to have a solid selection of props on hand. Just look at Leo — do you think he woke up that morning planning to grab a shellphone or swan and bust the most powerful pout the ’90s had seen? Of course he fucking did. And so should you.

What’s your ultimate ’90s Leo look? Let us know in the comments.

Want more vintage style? These are the best-dressed animated characters from the ’90s to mid-’00s.

Senior Staff Writer
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