© Dave Allocca

Fashion

Leonardo DiCaprio was a Nineties style icon

With Once Upon A Time In Hollywood about to hit screens, we've travelled back to once upon a time in... the Nineties. Our top discovery? A fair few style lessons from a young Leonardo DiCaprio

When Quentin Tarantino announced that his ninth feature – Once Upon A Time In Hollywood – would be an ode to the end of Hollywood's golden age, the sartorial sector of our brains started flickering. Would the director faithfully refashion the striking styles of 1969 Los Angeles? Thankfully, yes, and they're most obviously seen on frontmen Leonardo DiCaprio and Brad Pitt. It's no wonder Leo ended up in possibly the most stylish movie of the year: the former GQ cover star has a history of adopting the suavest outfits on screen, from Jay Gatsby of The Great Gatsby and Jordan Belfort of The Wolf Of Wall Street to Teddy Daniels of Shutter Island and Romeo Montague of Romeo + Juliet.

As it appears, landing a series of stylish roles has rubbed off onto DiCaprio's wardrobe. Or was it the other way round? As we've found through a delve into his archive, the Nineties proved he's a master of another art form: fashion. We all love a good throwback, especially when there's a fair few lessons to take from it. So as we say bon voyage to summer and welcome in the autumnal days, we're turning to a teen Leonardo DiCaprio for six serious style hacks. Master these and you're sorted for the season ahead.

© Steve Granitz

When: 19 April 1995

Tip to take: Easy does it. All you need is a pinstripe suit, white shirt and voilà, your formal attire is good to go. Just take a styling tip from 21-year-old DiCaprio: leave the top button of your shirt undone, layer its collar over your lapels and top it off with a beaded necklace. Smart nonchalance through simple styling.

© Ron Galella

When: 22 October 1993

Tip to take: Before there was Léon: The Professional (and the beginning of the black docker beanie obsession), there was Leo, the casual kid (and the kickstarter of the knitted accessory). The tip to take is simple: embrace the primary colours in your attire and match the materials of your cap to your mod-like knit.

© Dave Allocca

When: 1 November 1995

Tip to take: Sure, black leather is a statement, but brown leather is a sensation. DiCaprio really sells the rugged jacket here: weaved leather buttons, signs of wear round the collar and a battered touch to its body. Head to Brick Lane's finest vintage stores if you're in search of a faithful replica.

© Ron Davis

When: 23 June 1994

Tip to take: How to say hello to autumn? Through this kind of styling. Blue and beige are a leading combination for casual attire, so invest in a ribbed jumper like DiCaprio (one size up for the baggy effect) and sport it with some straight-cut denim jeans. Twenty-five years on, basic still works best.

© Ron Galella

When: 12 December 1993

Tip to take: Teen DiCaprio loved DIY-style accessories and that handcrafted necklace and tan leather belt work wonders over his heavily layered look. Get yourself some navy tailored trousers, a knitted cardigan and oversized suede shirt – that's day to night styling sorted.

© Barry King

When: 16 February 1994

Tip to take: Beads, beads and more beads! If you're looking to emulate Nineties Leo, that's what you need. But to finish we'll focus on that mandarin-collared shirt: easy, elegant and a striking staple under his oversized tailoring. For an upcoming gathering to sign off on summer, this styling is your best port of call.

Now read:

The early Nineties menswear looks we’ll be embracing this season

Will Smith and Jada Smith’s most iconic Nineties looks, ranked in order

Airport style was incredible in the '90s

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