Since his breakout role in “What’s Eating Gilbert Grape” in 1993, Leonardo DiCaprio has been a red carpet staple. In the 1990s, he often wore relaxed yet stylish outfits, such as Cuban-collared shirts and leather jackets.
After starring with Kate Winslet in 1997’s “Titanic,” his fame soared, and his style evolved accordingly. Over the years, DiCaprio has favored designs from luxury fashion houses like Giorgio Armani and Prada. Off-duty, the star of “The Great Gatsby” and “The Wolf of Wall Street” frequently pairs a baseball cap with relaxed T-shirt and jeans looks.
In honor of the “Killers of the Flower Moon” star’s 50th birthday, WWD takes a look back at Leonardo DiCaprio’s style evolution through the years.
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Leonardo DiCaprio, 1993
Image Credit: Eric Weiss/WWD Robert De Niro, Leonardo DiCaprio and Ellen Barkin attend “This Boy’s Life” New York premiere and after party at Rockefeller Center in New York City on March 15, 1993.
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Leonardo DiCarpio, 1998
Image Credit: Ron Galella Collection via Getty Actor Leonardo DiCaprio and actor Kate Winslet attend the 55th Annual Golden Globe Awards on Jan. 18, 1998 at the Beverly Hilton Hotel in Beverly Hills, California.
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Leonardo DiCarpio, 2004
Image Credit: Dave Bennett/Getty Images Sarah Ferguson, Princess Eugenie, actor Leonardo DiCaprio and Princess Beatrice arrive at the UK Premiere of “The Aviator” at the Odeon West End on Dec. 19, 2004 in London.
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Leonardo DiCaprio, 2006
Image Credit: Giovanni Giannoni and Tim Jenkins Leonardo DiCaprio in 2006.
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Leonardo DiCaprio, 2006
Image Credit: Stephane Feugere Leonardo DiCaprio at an event in 2006.
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Leonardo DiCaprio, 2007
Image Credit: Alexandra Wyman / Wire Image Kate Winslet and Leonardo DiCaprio at the Moet & Chandon Inside Ballroom at the 64th Annual Golden Globe Awards.
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Leonardo DiCaprio, 2009
Image Credit: Steve Eichner Leonardo DiCaprio at Vladimir Restoin Roitfeld’s post-exhibition party in February 2009.
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Leonardo DiCaprio, 2007
Image Credit: Jimi Celeste Leonardo DiCaprio in New York in 2007.
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Leonardo DiCaprio, 2007
Image Credit: Michael Caulfield/Wire Image Leonardo DiCaprio with Jonah Johnson at the Global Green USA 3rd Annual Pre-Oscar Celebration to Benefit Global Warming on February 21, 2007.
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Leonardo DiCaprio, 2009
Image Credit: Tyler Boye Leonardo Dicaprio on the red carpet For National Resources Defense Council (NRDC) 20th Anniversary Celebration at the Beverly Wilshire Hotel in Los Angeles, Cailfornia on April 25, 2009.
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Leonardo DiCaprio, 2009
Image Credit: Jeffrey Mayer/WireImage Leonardo DiCaprio at the Palm Springs International Film Festival Awards Gala in Palm Springs, California on January 6, 2009.
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Kate Winslet and Leonardo DiCaprio
Image Credit: Frazer Harrison/Getty Images Kate Winslet and Leonardo DiCaprio on the 2009 Golden Globes red carpet on January 11, 2009.
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Leonardo DiCaprio, 2009
Image Credit: Vicky Pombo Leonardo DiCaprio and Rima Al-Sabah in April 2009.
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Leonardo DiCaprio, 2010
Image Credit: Lexie Moreland Leonardo DiCaprio attends a party hosted by Giorgio Armani in honor of Martin Scorsese and Leonardo DiCaprio in honor of the “Shutter Island” premiere at Armani Ristorante on February 16, 2010 in New York City.
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Leonardo DiCaprio, 2011
Image Credit: Donato Sardella Leonardo DiCaprio with Eva Chow in Gucci for the LACMA Art + Film Gala Honoring Clint Eastwood and John Baldessari Presented By Gucci at Los Angeles County Museum of Art on November 5, 2011 in Los Angeles, California.
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Leonardo DiCaprio, 2013
Image Credit: Dave Allocca/Startraksphoto.com Leonardo DiCaprio in Prada and Jay-Z at a party for “The Great Gatbsy” in May 2013.
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Leonardo DiCaprio, 2013
Image Credit: Courtesy Photo Martin Scorsese, Giorgio Armani and Leonardo DiCaprio at the Giorgio Armani “One Night” event in December 2013.
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Leonardo DiCaprio, 2014
Image Credit: Amy Graves Leonardo DiCaprio at the 19th Annual Critics Choice Movie Awards Barker Hangar in Santa Monica, California in January 2014.
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Leonardo DiCaprio, 2014
Image Credit: Courtesy photo Leonardo DiCaprio and Bono on July 23, 2014 at the Leonardo DiCaprio Foundation inauguration gala.
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Leonardo DiCaprio, 2015
Image Credit: Evan Agostini/Getty Images Jack Nicholson, Mark Wahlberg, Leonardo DiCaprio and Matt Damon attend the Warner Bros. Pictures premiere of “The Departed” on September 26, 2006.
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Leonardo DiCaprio, 2018
Image Credit: Andrew H. Walker/WWD Martin Scorsese and Leonardo DiCaprio at the Museum of Modern Art’s 11th Annual Film Benefit presented by Chanel in New York, on November 19, 2018.
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Leonardo DiCaprio, 2022
Image Credit: Kevin Winter/Getty Images Leonardo DiCaprio attends the 92nd Oscars Nominees Luncheon on January 27, 2020 in Hollywood, California.
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Leonardo DiCaprio, 2023
Image Credit: Michael Buckner for Variety Leonardo DiCaprio and Lily Gladstone at the “Killers of the Flower Moon” Screening & Red Carpet at the 76th Cannes Film Festival held at the Palais des Festivals on May 20, 2023 in Cannes, France.
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Leonardo DiCaprio, 2023
Image Credit: Nina Westervelt for WWD Leonardo DiCaprio and Lily Gladstone at the 33rd Annual Gotham Awards held at Cipriani Wall Street on November 27, 2023 in New York City.
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Leonardo DiCaprio, 2024
Image Credit: Michael Buckner for Variety Leonardo DiCaprio at the 14th Governors Awards held at The Ray Dolby Ballroom at Ovation Hollywood on Jan. 9, 2024 in Los Angeles, California.
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Leonardo DiCaprio, 2024
Image Credit: Golden Globes Leonardo DiCaprio and Lily Gladstone at the 81st Annual Golden Globe Awards at the Beverly Hilton on January 7, 2024 in Beverly Hills, California.
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Leonardo DiCaprio, 2024
Image Credit: Gilbert Flores/Golden Globes Leonardo DiCaprio and Lily Gladstone at the 81st Annual Golden Globe Awards at the Beverly Hilton on January 7, 2024 in Beverly Hills, California.
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Leonardo DiCaprio, 2024
Image Credit: Gilbert Flores for Variety Leonardo DiCaprio and Lily Gladstone at the 2024 Palm Springs International Film Festival Film Awards held at the Palm Springs Convention Center on January 4, 2024 in Palm Springs, California.