To celebrate the Hollywood heartthrob's milestone birthday, we take a look at some of his most iconic looks of all time ...

Since starring opposite Robert De Niro in 1993's This Boy's Life, Leonardo DiCaprio has truly been king of the Hollywood ... arms outstretched Jack Dawson-style? Which he more or less checked off the ...

Picture this: Hollywood in the ’90s, a time of flannel shirts, hair gel, and a duel of heartthrobs. Enter Johnny Depp and Leonardo DiCaprio, who could be the best of buds. But oh, how ...

The reality is Leonardo DiCaprio is part of that generation that gained notoriety in the '90s and perhaps, for the last time ...

When talking about Leonardo DiCaprio, many, besides recognizing the career of one of the most acclaimed actors of the last 30 ...

Will Leonardo DiCaprio be feeling like the King of the World when ... DiCaprio (pictured with Johnny Depp) sporting classic 90s boyband-style curtains Credit: Getty Leo was critically acclaimed for ...

Hollywood star Leonardo DiCaprio got an early start on his 50th birthday celebrations with a grand bash on Saturday.

In the court of public opinion, anyone who attended Sean “Diddy” Combs’ infamous gatherings, including his 90’s white parties ...

Over two years after her divorce from Tom Brady, Gisele Bündchen is charting a new path for herself in both her professional ...

Gigi Hadid Hits Tom Ford Runway After Seen Getting Close with Leonardo DiCaprio at NYFW Party Tom ... Tom Ford Stella McCartney Leads Tributes as Fashion Industry Mourns Tom Ford's Late Husband ...

Style a black corset top with black skinny ... An impressive Jay Gatsby (Leonardo DiCaprio) costume inspired by the 2013 film adaptation The Great Gatsby consists of a suit (white, tan or black ...

As part of this year's TODAY Halloween Theme, "VHS Rewind," Hoda dressed up as DiCaprio’s Jack Dawson and Jenna transformed ...