There is a particular era of 90s fashion that we owe to three men: River Phoenix, Keanu Reeves and Leonardo DiCaprio. The trio, who all became juggernaut stars of the decade, quietly used style to inform the way their acting careers were unfolding and in turn, helped define the grunge aesthetic trends of 90s menswear too.
If Leo’s on screen roles and outfits (think: the ragtag suspenders of Jack in Titanic or his unbuttoned botanical print shirt in Romeo + Juliet) made him a Hollywood heartthrob, his own wardrobe was more defined by low-key Americana looks and rebelling against black tie codes. Here, as his Martin Scorsese directed epic Killers of the Flowers Moon hits cinemas, we look back at some of Leo’s most iconic outfits of the 90s.
At an AIDS fundraiser, 1992
Two years before starring as the drug-addicted teen in The Basketball Diaries, and a year before his What’s Eating Gilbert Grape breakout, a baby Leo rocked up to an MTV-held AIDS basketball fundraiser in full regalia. For the event (in which we assume he partook), he wore a Champion basketball jersey, white Nike tube socks and a pair of black Air Maestro Flights, a silhouette long-gone out of production. But the real piece de resistance? The triple-layered basketball shorts. An inexplicable but otherwise iconic flex.
Subscribe to i-D NEWSFLASH. A weekly newsletter delivered to your inbox on Fridays.
At the What’s Eating Gilbert Grape premiere, 1993
In what would become a rare moment of creative casualwear for Leo, he showed up to the premiere of What’s Eating Gilbert Grape alongside co-star Johnny Depp. Forgoing a suit or a standard T-shirt and jeans look, Leo paired navy slacks and a tan belt with a ribbed cardigan layered beneath a contrast stitch workman jacket. As would become standard, it’s the accessories that make it memorable: a red and blue friendship-style beaded necklace.
In New York City, 1993
The year is 1993 and Leonardo DiCaprio is quickly becoming Hollywood’s hot property. Having just turned 19, he was in New York City (presumably doing press for What’s Eating Gilbert Grape) when this picture was taken. In it, we see the first proper look at Leo’s relaxed personal style, at the time akin to industry peers like River Phoenix and Keanu Reeves. Leo layered a basic white T-shirt under a black fine-knit sweater, pairing the top half with the 90s go-to, blue jeans. But it’s the accessories that pop here: not only is Leo rocking a snake-chain necklace, but a silver chain attached to the waist of his jeans.
Departing LAX, 1993
In the midst of promo on his first feature film (the underseen This Boy’s Life), Leo flexed this airport look for an LA paparazzo as he prepared to board a flight to Dallas, Texas. A standout image that seems to carry 90s teen style culture, Leo layered a terry polo shirt under a classic grey jersey sweatshirt, alongside his go-to blue denim and a pair of Puma Suedes. This is one of the first photos we’d get of him wearing a baseball cap (this one bears the mascot of a Cleveland team) — an accessory he’s still wearing regularly today.
At the Golden Globes, 1994
With What’s Eating Gilbert Grape deemed a critical success, Leo had become American cinema’s new-found heartthrob — and racked up a Golden Globe and Oscar nomination in the process. In early 1994, Leo turned up to his first Globes in a red carpet look that remains his most ostentatious. Breaking formal codes, Leo paired his super wide-lapelled tuxedo jacket and chequered waistcoat with a monk-neck shirt — no bow tie. Intentional style statement or not, it aligned perfectly with his public positioning as the new kid on the block: roguish, and willing to take risks.
On the red carpet with Gwyneth Paltrow, 1994
Weeks after his Globes red carpet appearance, Leo was invited to the National Board of Review awards ceremony in New York. Having flaunted his laidback take on black tie a few weeks prior, here he opted for a preppier formal look. Spotted on the red carpet alongside Gwyneth Paltrow, he wore another monk neck collared shirt, this time paired with a slouched navy corduroy suit.
Front row at Versus Versace, 1997
In 1997, as the fashion world went starry-eyed over Leonardo’s turn in Romeo + Juliet — not yet aware that he’d soon become the star of the biggest movie ever made, Titanic — Leo made a rare visit to fashion week. Despite the fact that his looks are retroactively celebrated, Leo wasn’t formally engaged with the fashion world in the manner that many celebrities of his calibre were at the time. His appearance at the 1997 Versus Versace show, mere months before Gianni passed, was therefore a real surprise. He went low-key for the affair and sat front row in a casual black suit and wide-collared brown shirt. Once again, it’s his accessories that stand out: those sunset orange-tinted glasses, rimmed with gold, are eyewear catnip to 2020 fashion enthusiasts.