Along the way, he's managed to get a bevy of model beauties hanging off his arm, including Gisele Bundchen, Bar Refaeli, and Erin Heatherton.
He must know a thing or two about looking good, then? Well, yes and no... decided for yourselves in our Leonardo DiCaprio style round-up...
- 1990<p> Aww. Fresh-faced and cute as he starts out in <em>Parenthood</em>.</p>
- March 1997<p> Leo opted for tinted shades and a slick-Rick hairstyle at the London film premiere of <em>Romeo and Juliet</em>.</p>
- November 1997<p> The London premiere of <em>Titanic</em> saw Leonardo pull on a tux and bow tie, as well as a shy smile for the camera.</p>
- January 1998<p> Clean-cut and clean-shaven, Leonardo DiCaprio made a handsome red carpet date for Kate Winslet at the 55th Annual Golden Globe Awards in Beverly Hills, LA.</p>
- February 2000<p> A charcoal suit and dove-grey shirt had Leo looking cute at London premiere of <em>The Beach</em>.</p>
- May 2000<p> Specs appeal: Leonardo DiCaprio ensured he wouldn't miss any of the action court side at a Los Angeles Lakers game with celeb pal Tobey Maguire.</p>
- May 2002<p> Leonardo DiCaprio got suited and booted for the <em>Gangs of New York</em> premiere at the Cannes Film Festival in 2002. Just one question: what is Cameron Diaz (not) wearing?</p>
- December 2002<p> Leonardo DiCaprio grew some facial fuzz for a screening of<em> Gangs of New York</em> in LA.</p>
- December 2002<p> Leonardo DiCaprio grew some facial fuzz for a screening of <em>Gangs of New York</em> in LA</p>
- January 2003<p> At a <em>Gangs of New York</em> press conference in Berlin, Leonardo tried to keep his look relaxed with a jumper and trainers as he was joined by director Martin Scorsese.</p>
- February 2003<p> Leo obviously wanted to be taken seriously as he spoke at a conference promoting the use of fuel-efficient cars in LA, and donned a teacher-worthy beige corduroy jacket.</p>
- April 2003<p> Los Angeles Lakers fan, much? Leonardo DiCaprio cheers on his team as they won playoffs in Minneapolis wearing one of their namesake shirts and a matching cap.</p>
- June 2004<p> As much as it pains us to say anything bad about Leo, we're not digging the baggy jeans and trainer ensemble at the screening of <em>Fahrenheit 9/11</em> in New York.</p>
- July 2004<p> After enjoying lunch at Bar Piti in New York, Leo worked it off by heading home on a bike, and looked laidback in red shorts and a T-shirt.</p>
- December 2004<p> Leo slicked back his hair and donned a silver tie as he joined a stunning Kate Beckinsale on the red carpet at a screening of<em> The Aviator</em> in LA.</p>
- December 2004<p> Leo joined another of his glamorous leading ladies, Cate Blanchett, at the London premiere of <em>The Aviator </em>and looked dapper in a mid-suit.</p>
- February 2005<p> Working a silk-lapelled suit and greased-back hair, Leo took to the Oscars red carpet with his stunning ex-flame Gisele Bundchen.</p>
- October 2006<p> Leonardo was tanned, happy and relaxed as he joined Vera Farmiga at the screening of <em>The Departed </em>during the Rome Film Festival.</p>
- December 2006<p> With his cropped hair, smouldering eyes and smart pinstripe suit, Leonardo DiCaprio was quite the leading man at the LA premiere of <em>Blood Diamond</em>.</p>
- February 2007<p> Co-stars Leonardo DiCaprio and Mark Wahlberg celebrated as <em>The Departed</em> won Best Film at the 2007 Oscars - and doesn't Leo look handsome?</p>
- December 2007<p> Sporting what looks like darker hair and a matching facial mane, Leo's baby blues were sparkling at the Marrakech International Film Festival Opening in Morocco.</p>
- November 2008<p> Teaming a navy sweater with pinstripe trousers, Leo was looking on fine form at a photocall for <em>Body of Lies</em> at the Bristol Hotel in Paris.</p>
- December 2008<p> Both Leonardo DiCaprio and Kate Winslet showed off one of their best looks at the LA premiere of <em>Revolutionary Road</em>.</p>
- February 2009<p> Even when he's just grocery shopping with Bar Refaeli, Leo looks cute in a leather jacket and baseball cap.</p>
- February 2009<p> Leo covered up in a cool long coat at the Cinema for Peace Gala at the 59th Berlinale Film Festival. Shiny shoes and a goatee finished the look.</p>
- February 2010<p> Leo proved he's a man of the people as he took pictures with fans at the world premiere of <em>Shutter Island</em> at the International Film Festival Berlinale in Berlin.</p>
- July 2010<p> Leonardo played the gentleman and managed to look very suave at the same time during the <em>Inception </em>premiere in London.</p>
- July 2010<p> Jeans + trainers + backward cap = least favourite Leo look ever? The actor arrived at Narita International Airport in Narita, east of Tokyo, looking less than stylish.</p>
- November 2011<p> Too much sun, or too much foundation? Leo looked a tad orange at the <em>J Edgar</em> premiere in LA.</p>
- January 2012<p> We love Leonardo's sleek look at the 17th Annual Critics' Choice Movie Awards in LA. Everything from the form-fitting suit to the slight tan and sexy stubble gets a tick from us.</p>
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