In 2016, an Internet meme died. After five nominations, Leonardo DiCaprio finally won the Oscar for Best Actor for The Revenant. This was after years of an amazing career that had started off as a last-season star of Growing Pains. That led to roles that played on his good looks before the mega-success of Titanic launched him into the stratosphere. But DiCaprio didn’t play the game as expected, foregoing blockbuster movies for the most part to take on roles he found more challenging. It earned him respect, showing he wasn’t just handsome, but also a truly talented actor who shined well in any part. The Oscar was the topper, his turn as a man surviving the elements of the 19th century forest a huge success that deserved the Oscar.
Through his career, DiCaprio has played nearly every role, many of them taking place in the past. Thus, a lot of outfits can’t be worn today (no one in their right mind goes around with the clothing of The Man in the Iron Mask). But DiCaprio has a unique quality that manages to make any outfit he’s in look like he just stepped out of GQ magazine. Even stuff that’s supposed to be stuck in a period piece could be successful worn today by the actor thanks to how he gets so well into each character he plays. While some costumes are better off left in the film, there are others that DiCaprio can keep in his closet to use. Here are 15 outfits DiCaprio can wear in real life, showcasing his amazing range of films.
15 Body Shades
Ridley Scott is well known for major epics like Gladiator and Blade Runner. But he can also do a surprisingly conventional spy thriller such as Body of Lies. DiCaprio played a CIA operative in the Middle East who soon gets involved in a highly complex investigation. As he digs deeper, aided by an elder agent Russell Crowe, he realizes the whole thing is a mess of politics, and that he can't really trust anyone.
DiCaprio looks dashing as expected in the role, dressed not too classy in order to become the spy he needs to be. What really stands out are the awesome sunglasses which are clearly top of the line. This is a realistic movie, so no fancy James Bond-style gadgets, just regular shades. But somehow, DiCaprio makes them look cool as hell as he goes through these assignments. It takes a lot to look steamy when you’re in the desert, but DiCaprio managed to elevate the movie with his style and looking cool in the sun.
14 Young Hoover
Casting DiCaprio as J. Edgar Hoover seemed an odd choice. The FBI boss is infamous for his temper, his lust for power and control, often spying on prominent Americans and the rumours of dressing in women’s clothing. Clint Eastwood’s movie was chastised for trying to make Hoover more heroic, ignoring the man’s dark side at times and not good in story. But DiCaprio did win raves for his performance going from the young and eager Hoover to an aged man crushed by his own power.
Most of the role has him in suits, and it’s impressive seeing the younger DiCaprio pulling these styles off. A few of the tweed outfits could still work today, an old style but a classic one that still looks terrific. True, DiCaprio goes for more of a “everyday” style in clothing, but this suit allows him to look more than desirable.
13 Court Shirt
In 1995, DiCaprio was coming off his star-making, Oscar-nominated turn in What’s Eating Gilbert Grape but still getting a lot of “teen heartthrob” roles. But he wanted to show he was a serious actor, and that's how he landed a role within The Basketball Diaries. The story was about Jim Carroll, a high school basketball star who soon fell deep into drug use. DiCaprio wowed critics by showing his character going from a clean-cut young kid to a darker mess and showing his great talent off.
He did his own playing on the court with a muscle shirt showing a build that was thin but still not bad. Much of the movie is focused on his collapse into heroin addiction and crawling his way out, the first true sign of the amazing actor DiCaprio was. He might not fit into the same shirt today but given he’s more athletic, DiCaprio can wear such a top now and still sink a few baskets to remember a groundbreaking part.
12 Gang Leader
Delayed for a year, Martin Scorsese’s epic Gangs of New York opened in 2002 to some rough times. Not as successful at the box office as hoped, it also failed to be the major Oscar contender fans wanted. DiCaprio was a young man whose father had been killed by the brutal “Bill the Butcher”played by Daniel Day-Lewis, and grows up lusting for revenge. He joins Bill’s gang to get closer to him but soon realizes the man has the power to truly rule New York. Gripping and powerful, the film got attention for DiCaprio dirtying it up, many of the fashions too old-school to work.
However, one outfit that would work today is his nice dark shirt and pants that he uses in a barroom brawl scene. It’s a nice outfit that can look stylish by today’s standards (and in fact might be criticized for looking too good for the period). While the movie is rather gritty, DiCaprio makes it look terrific.
11 Gatsby Class
There have been a lot of versions of F. Scott Fitzgerald’s classic novel. But the 2013 one was wild thanks to Baz Luhrmann directing it in 3-D with a unique touch. DiCaprio was the man himself, Jay Gatsby, a rich man in the 1920s who loves a party life. But behind it is a deep secret that he tries to hide behind his flash and sizzle. The movie was polarizing with critics praising the performances and direction but criticized for modern music and some feeling it was more style than substance.
DiCaprio was clearly in command as Gatsby, showing off in a variety of great suits. This party tuxedo is amazing, just the sort of thing you’d see DiCaprio wearing at an awards ceremony. The image of him in the movie holding up a champagne glass has become a highly popular meme used for various “toasts” and that’s a testament to DiCaprio’s charisma to make a century old outfit hotter than anything today.
10 Road Outfits
In 2008, a decade after Titanic, DiCaprio and Kate Winslet finally reunited on screen. Revolutionary Road tracked the lives of a couple from meeting, falling in love, a hot early relationship, starting a family and then slowly coming apart. As before, the chemistry between the two was fantastic to sell the story and boosted them up further. The film is a bit famous for how Winslet won practically every Best Actress award there was for it…only to win the Oscar for The Reader instead. The two delivered an intense and wonderful performance.
DiCaprio fit the 1950s fashions and as he often does, made them look as stylish as they could be today. The two of them together made such an aesthetically pleasing couple, that really, it didn't matter what they were wearing.
9 High Flier
A highly complex man, Howard Hughes was a genius inventor and ace pilot who built up an industrial empire to be one of the richest men in America. He was also saddled with massive mental issues of compulsive behavior and his genius often overreaching his grasp. The Aviator has DiCaprio as Hughes in his prime, showing his daring and how his demons pushed him to success but undermined it as well. The film is best known for Cate Blanchett in her Oscar-winning turn as Katherine Hepburn (one of Hughes’ many loves), but DiCaprio turned in a fine performance capturing the complex figure well.
This outfit is well put together; the bomber jacket that DiCaprio confessed to taking from set, as he enjoyed it, and the old-styled fedora still looking stylish today. DiCaprio has a great knack for making “older” outfits look terrific and this is a fine example of how Hughes was so ahead of his time. This clothing would do well today.
8 Wolf Partier
The last try at an Oscar before his eventual win, The Wolf of Wall Street had DiCaprio doing a great job. He was Jordan Belfout, the real-life man who rose from a stockbroker to one of the richest men on Wall Street. But the same drive and ego that led to his success also caused him to shatter rules that led to his downfall with his firm taken down.
DiCaprio threw himself into replicating the money-mad man of the 1980s with both suits and parties. This is one such outfit; the nice polo shirt and light pants a good combo, flaunting his wealthy style, but making it casual enough that he is not totally intimidating. The movie is probably best known for Margot Robbie’s scene-stealing, star-making nude turn and her romps in the sack with DiCaprio. However, it’s one of his better roles and can party in this outfit anytime he wants.
7 The Beach Trunks
After the monster success of Titanic, DiCaprio took a bit of a break to get his next project. He made an offbeat choice with this story of a group of young folk exploring a remote island. Naturally, the idea of DiCaprio going mostly shirtless was a thrill to female fans but the movie itself was deep if sometimes bizarre. One sequence has him marching through the jungle like a video game and there’s his dark romance with the island tribe’s boss played by Tilda Swinton. The movie was a bit of a disappointment with many feeling DiCaprio could have gone for something more commercial. But he defends it as a choice in the role and that played a part in his later success.
The trunks he wears are comfortable, stylish but not flashy, just the sort of thing you’d see folks wearing at the beach anywhere. Given how many times he’s been photographed at the beach with a variety of gorgeous women, it says a lot these look better than of DiCaprio’s other beach wear.
6 Romeo’s Street Style
It could have been a disaster but instead worked out. In 1996, Baz Luhrmann gave the Shakespeare masterpiece a modern twist. He relocated the story to modern Los Angeles with the Montagues and Capulets rival gangs but retaining the classic language. DiCaprio was Romeo with Claire Danes as Juliet and the two had wonderful chemistry (despite reports of not getting along well behind the scenes).
While the “armor” he wore for the costume party where they meet was good, Romeo’s “street style” was better. He wore dark shorts with a Hawaiian t-shirt, mostly open to show his pecs off. Seeing a guy dressed like that, while spouting Shakespearean talk was a little strange, but he pulled it off and got the praise he deserved. Not only did it show his talents, but we learned that Leo is one of the few who could pull off such a busy, colorful shirt.
5 Catch Me Pajamas
In 2002, DiCaprio finally got the chance to work with Steven Spielberg. The acclaimed director chose DiCaprio for the role of Frank Abagnale, one of the most famous con artists of all time. Looking older than his years, the man, by just 19, had scammed millions out of cons posing as anything from a doctor to a Pan Am pilot in the 1960s. The movie focuses on his cat-and-mouse game with Tom Hanks as the FBI agent trying to bust him. DiCaprio is fun as this overgrown kid who sees the whole thing as a game, the money less important than the thrill of it all.
The sight of him in a pilot’s uniform is good but a more likely outfit for him are the pyjamas he wears in bed. They’re an old style, but classic and look comfortable enough for him to wear in the film with his latest female conquest. It was a role that showed his great charm off, and how even an old-styled outfit can fit him well today.
4 Blood Diamond Khakis
When DiCaprio was nominated for Best Actor in 2007, it wasn’t a surprise. What was however, was that rather than being nominated for The Departed, it was for Blood Diamond. The movie had been mostly forgotten and thus DiCaprio was honoured by the Academy for giving it a nomination. DiCaprio got a chance to take on an accent, playing a South African mercenary locked in jail with a fisherman played by Dijmon Hounsou. Escaping, they strike a bargain as DiCaprio will help Hounsou rescue his family from a warlord in exchange for a priceless diamond the fisherman hid. The movie was criticized for going too much in the politics of the region.
Leo however, looked good in the jungle wear of khakis. It was a cool and comfortable look that blended in well with the setting. DiCaprio is active in environmental efforts so this could be an outfit he’d wear for real while traveling and look good doing it. The role itself may not be his best but DiCaprio can live the jungle life well.
3 Inception Style
Christopher Nolan’s mind-bending movie has DiCaprio as the leader of a team who enters people’s dreams in order to steal secrets. That’s the basic plot but trying to actually understand the film takes a lot more time and effort. That includes the ending which remains massively debated today.
DiCaprio does look great in it, with a variety of cool suits, selling himself as a tough guy who can get down and dirty if he has to in fights. He can move from a gun battle to working as a complex con and handling the loss of a love in the past. As this is mostly a dream world, he can justify being dressed in stylish clothing, all of which makes him look very dashing and sleek. The movie is known for its stunning visuals and wild story but DiCaprio grounds it with his performance. His outfits and general way of being handsome makes you wish that those dreams were real.
2 The Departed Cap
One person who can sympathize with DiCaprio’s lack of Oscar luck would be Martin Scorsese. Despite being acclaimed as one of the finest directors ever, he kept coming up short at the Oscars even with classics like Taxi Driver, Raging Bull and Goodfellas. In 2007, Scorsese finally got the gold as The Departed won Oscars for Best Picture and Director. The gripping crime drama had DiCaprio as a cop who goes undercover in a mafia family run by Jack Nicholson. Matt Damon is a gangster going undercover as a cop as the two clash.
DiCaprio had a good vibe in the role, selling a tough Boston accent and a disguise that includes a Red Sox cap. DiCaprio could wear that well in Boston, looking perfect in the outfit of jeans and dark shirt, like any other guy going to a ball game. It was a great flick, and this outfit is one that shows DiCaprio looks good dressed in street clothes.
1 The Titanic Tux
It’s the movie that elevated him to mega-stardom. It’s hilarious looking back 20 years to everyone convinced James Cameron’s $200 million film (an absolutely unheard of amount back then) which was going to flop badly. Instead, to the shock of Hollywood, the movie dominated the top of the box office for fifteen straight weeks, becoming the highest grossing film ever and winning eleven Oscars. DiCaprio was the highlight as Jack, the young gambler who wins a place on the ship and falls madly in love with socialite Rose (Kate Winslet). Invited to dinner, Jack is totally out of place but Molly Brown (Kathy Bates) loans him one of her son’s tuxedoes.
DiCaprio just looks quite dapper in it, with the fun touch of how people literally don’t recognize him at first. He’s charming over dinner, fiddling a bit with the suit, and it’s no wonder Rose swoons for him. He later takes the coat off to treat Rose to a fun party with the third class passengers but this tux remains a great outfit. We can see DiCaprio easily wearing one like it to give a nod to his most famous role.
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