1990
Aww. Fresh-faced and cute as he starts out in Parenthood.
1997
Leo opted for tinted shades and a slick-Rick hairstyle at the London film premiere of Romeo and Juliet.
1997
The London premiere of Titanic saw Leonardo pull on a tux and bow tie, as well as a shy smile for the camera.
1998
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.
2000
A charcoal suit and dove-grey shirt had Leo looking cute at London premiere of The Beach.
2000
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.
2002
Leonardo DiCaprio got suited and booted for the Gangs of New York premiere at the Cannes Film Festival in 2002. Just one question: what is Cameron Diaz (not) wearing?
2002
Leonardo DiCaprio grew some facial fuzz for a screening of Gangs of New York in LA.
2002
Leonardo DiCaprio grew some facial fuzz for a screening of Gangs of New York in LA
2003
At a Gangs of New York press conference in Berlin, Leonardo tried to keep his look relaxed with a jumper and trainers as he was joined by director Martin Scorsese.
2003
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.
2003
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.
2004
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 Fahrenheit 9/11 in New York.
2004
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.
2004
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 The Aviator in LA.
2004
Leo joined another of his glamorous leading ladies, Cate Blanchett, at the London premiere of The Aviator and looked dapper in a mid-suit.
2005
Working a silk-lapelled suit and greased-back hair, Leo took to the Oscars red carpet with his stunning ex-flame Gisele Bundchen.
2006
Leonardo was tanned, happy and relaxed as he joined Vera Farmiga at the screening of The Departed during the Rome Film Festival.
2006
With his cropped hair, smouldering eyes and smart pinstripe suit, Leonardo DiCaprio was quite the leading man at the LA premiere of Blood Diamond.
2007
Co-stars Leonardo DiCaprio and Mark Wahlberg celebrated as The Departed won Best Film at the 2007 Oscars - and doesn't Leo look handsome?
2007
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.
2008
Teaming a navy sweater with pinstripe trousers, Leo was looking on fine form at a photocall for Body of Lies at the Bristol Hotel in Paris.
2008
Both Leonardo DiCaprio and Kate Winslet showed off one of their best looks at the LA premiere of Revolutionary Road.
2009
Even when he's just grocery shopping with Bar Refaeli, Leo looks cute in a leather jacket and baseball cap.
2009
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.
2010
Leo proved he's a man of the people as he took pictures with fans at the world premiere of Shutter Island at the International Film Festival Berlinale in Berlin.
2010
Leonardo played the gentleman and managed to look very suave at the same time during the Inception premiere in London.
2010
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.
2011
Too much sun, or too much foundation? Leo looked a tad orange at the J Edgar premiere in LA.
2012
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.