Leonardo DiCaprio's Most Stylish Roles

25.

Leonardo DiCaprio has a history of picking out some well-dressed roles. From men like Howard Hughes in The Aviator to his turn as "Jay Gatsby" in The Great Gatsby, he's played some parts that require some serious dressing up. Being the avid cinephiles that we are, we sifted through his oeuvre (including obscure flicks like Don's Plum and The Foot Shooting Party, you film snobs) to find the parts with the freshest kits. And then we ranked them, because we're crazy. So sit back (consider pouring a stiff drink to get in the mood) and take a look through Leonardo DiCaprio's Most Stylish Roles.

24.Richard

Film: The Beach

Year: 2000

Signature Look: Stranded Gnarbro

With his frosted tips, tribal T-shirt, beaded necklace, and penchant for shirtlessness, Richard embodied the archetype of "boy band cool." Granted, he was a college bro on vacation, and his "eternal tourist" look captures that perfectly. This is the clueless bro who goes to exotic places like Borneo to "find himself" when really he just wants to find some "croosh waves" and smash some totally foreign babes. Ugh. This guy sucked in college.

23.William "Billy" Costigan Jr.

Film: The Departed

Year: 2006

Signature Look: Hard-Boiled Boston Cop

South Boston cop Billy Costigan dresses like he's from Boston-tough as hell, and with a Red Sox cap. His loose-fitting workwear make him look like a low-level thug, which works well with his undercover steez, but he gets extra points for that black washed Levi's Trucker Jacket and the hardy leather Belstaff coat he layers over a hoodie in one of the film's pivotal scenes. He's not your typical action hero, he's dressed like the anti-James Bond-not suave, but pragmatic and ready to get his hands dirty.

22.Hank

Film: Marvin's Room

Year: 1996

Signature "look": "I Listen to Grunge, Dude"

Trooubled teen Hank has a style with a similar appeal to Shawn Hunter from Boy Meets World, it paints him as the rebellious type, without going too overboard. Hands down his best outfit is when he's rocking those cool shades with the indigo polo shirt, but he manages to wear a cool tonal navy-on-navy look and also pulls off a ringer tee. And of course, the film shares a title with acertain Drake song.

21.Brandon Darrow

Film: Celebrity

Year: 1998

Signature Look: A Living, Breathing Calvin Klein Ad

Brandon Darrow is a very meta character, and sort of a parody on DiCaprio himself. A popular young actor with enjoying the status of a hearthrob, the Marlon Brando to thank for it.

20.Arnie Grape

Film: What's Eating Gilbert Grape?

Year: 1993

Signature Look: "Derelicte"

True, Arnie Grape's state of uncouthness is explained by a fear of water he develops in the course of the film, but aside from that, he has some truly stylish moments. The yellow button-down with the red hat and tie works without making him look like a McDonald's employee, while the camo T-shirt, hoodie, and washed denim is an outfit you'd still see on dudes running around the streets today.

19.Jim Carroll

Film: The Basketball Diaries

Year: 1995

Signature Look: Heroin Chic, obviously

Jim Carroll starts off as a respectably preppy dude until he falls harder into drugs and begins to resemble a shell-shocked Vietnam Veteran. His cut-off basketball shirts, worn-in fatigue jacket, and ripped-knee jeans might have been grunge style staples, but here they perfectly show his descent into darkness... but is it super messed up for us to admit that he kind of looks cool that way?

18.Teddy Daniels

Film: Shutter Island

Year: 2010

Signature Look: Noir Detective (On Vacation?)

From the get-go Teddy Daniels' Hawaiian floral tie is a tip-off that either something's amiss, or these U.S. Marshals have one hell of a lax dress code. The noir look suits this character extremely well, and given the nature of the film's plot, Daniels' layered look is indicative of the levels in the film's story.

17.Josh

Film: Critters 3

Year: 1991

Signature Look: Wavy T-shirts

DiCaprio's first role made him an instant style icon. Just look at those amazing T-shirts! If they came out today from a streetwear brand, we'd line up for them. Plus he really knows how to accessorize: with a Game Boy, duh.

16.Roger Ferris

Film: Body of Lies

Year: 2008

Signature Look: Hypebeast of Arabia (technically Iraq, but whatever)

Leo had been running around Africa in Blood Diamond decked in ho-hum safari gear, but in Body of Lies CIA agent Roger Ferris pops up in Iraq wearing this amazingly streetwear-appropriate ensemble. The chambray bucket hat, navy vest with corduroy yoke, and numbered long sleeve shirt look like they came out of a street style post. The graphic placement on that shirt wouldn't seem out of place if say, Hood By Air printed a similar version. And the sunglasses? Those totally give him a Hunter S. Thompson vibe. Ferris' streetwear moment take an otherwise tepid film and make it a little more awesome.

15.Dominic Cobb

Film: Inception

Year: 2010

Signature Look: Ambiguous Futuristic Mastermind

Dom Cobb is one of DiCaprio's most awesome roles, but it's a far cry from one of his most stylish. While he holds his own in leather jackets and slim suits, he's easily outshined on the screen next to dudes like Joseph Gordon-Levitt (who kills in in a perfect brown leather jacket and expertly-tailored three-piece suit) and Cillian Murphy, whose double-breasted suit blows away DiCaprio's peak-lapeled, single-breasted suit. Well, you know what they say... haters gonna hate.

14.Calvin J. Candie

Film: Django Unchained

Year: 2012

Signature Look: Filthy Rich, Filthy Racist Slave Owner

Meet the original well-dressed douchebag. Calvin Candie shows how evil can come in many forms, and that plenty of times, monsters are much uglier on the inside than the outside. While the despicable villain doesn't hesitate to dress to the elevens, his clothes are a symbol power, they're bright, expensive as hell, and meant to remind everyone around him that he's better than them.

13.Frank Wheeler

Film: Revolutionary Road

Year: 2008

Signature Look: American Dream Aspirant

Ironic that this character is named "Frank Wheeler," as his goal in life is to be a cog in the American machine. As such, he wears a lot of drab colors and suits with patterned ties that hint at the dreams he has underneath. When he's at home or dressed casually, his short-sleeve buttondowns convey his carefree attitude and the newfound "leisure time" that many Americans were starting to enjoy post-WWII. He'd be higher on this list if his style was meant to signify who he actually was, rather than sheep's clothing he put on because he thought that was expected of him.

12.King Louis XIV/Philippe

Film: The Man in the Iron Mask

Year: 1998

Signature Look: #KINGSHIT

Sorry Joffrey Baratheon, King Louis XIV has you beat for most stylish king and most annoying prick. Although his twin Philippe was pretty much the original Iron Man (what with that mask and all), King Louis' royal garb is straight lavish. The intricate patterns and regal fabrics remind peasants of their own poverty just by looking at them.

11.Amsterdam Vallon

Film: Gangs of New York

Year: 2002

Signature Look: Street Rat Sprezzatura

Amsterdam has that "unstructured but dressed up" look down centuries before #menswear did. Plus, we don't think anyone else wears the cabbie-style cap better. He proveshimself a style icon when, in true punk fashion, he dip-dyes his shirt in rabbit's blood, no doubt creating the DIY movement and inventing colorblocking at the same time. Today's gangsters... they have it so easy with their bandanas and colors.

10.Fee "The Kid" Herod

Film: The Quick and the Dead

Year: 1995

Signature Look: Red DiCaprio Redemption

This young gunslinger is literally dressed to kill. From brown three-piece suits to sharp cowhide jackets with coordinating bandanas, the rugged clothing provides a sharp contrast to the otherwise youthful face wearing it. They're clothes that are meant to show the Wild West is a place where you grow up fast, or else you may not get the chance to grow up at all.

9.Arthur Rimbaud

Film: Total Eclipse

Year: 1995

Signature Look: Suuuuper Wasted Pirate

Poet Arthur Rimbaud has a penchat for club collars, cravats, smoking, and going totally apeshit. Essentially, he's the gay artistic dude you meet at every other party who has probably tried every drug under the sun, which is pretty much what Arthur Rimbaud does throughout the film. His rakish look and pleated, band collar shirts will live on forever.

8.Jack Dawson

Film: Titanic

Year: 1997

Signature Look: Ashy to Classy

It's no wonder that Jack Dawson is the crush of so many teenage girls. His style embodies how most women would want a man to dress: comfortable most of the time, but cleans up really well. His workwear-inspired, rough-around-the-edges style works for him, pulling off tab collar shirts and corduroy pants with ease, stuff you could easily find at a J. Crew store today. But his sudden transformation from intriguing bad boy to dapper gent really seals the deal. He's like the guy that knows everything about style, but doesn't want to go all-out unless he has to.

7.J. Edgar Hoover

Film: J. Edgar

Year: 2011

Signature Look: Conservative Hard-Ass

J. Edgar's style is dictated by the time, but that doesn't mean he doesn't look awesome in it. This movie is a visual love letter to the peak lapel, with the titular character wearing it proudly on most of his suits. Even his tuxedo has an impressive double-breasted peak lapel blazer. When's not wearing that, he switches it up for an attractive brown tweed three-piece suit, and a couple of warm-looking brown tweed topcoats that would get him street styled in an instant if he wore them today.

6.Tobias "Toby" Wolff

Film: This Boy's Life

Year: 1993

Signature Look: 50s Americana

Toby went from striped graphic tees to a killer haircut pretty fast. His slicked-back 'do was a staple of Greaser style, and while he never donned a motorcycle jacket, his sweater and outerwear game was on point. From argyle cardigans with repp stripe neckties to dotted and fair isle crewneck sweaters, his knit game was enough to probably make Drake jealous.

5.Jordan Belfort

Film: The Wolf of Wall Street

Year: 2013

Signature Look: Quaalude Cozy Boy

You're probably expecting this to be a profile of DiCaprio's wild, '80s-era suiting, and of course, that's an important part of his portrayal of the slick Wall Street tycoon Jordan Belfort. From Belfort's Armani-esque suits during those penny stock beginnings, to the pinstriped, shoulder-padded jackets that symbolized his later Wall Street successes, Belfort's business attire was the perfect, clean-cut contrast to his sinister moral interior.

But without a doubt, the most flexworthy fit in this entire movie has to be Beflort's off-duty, Quaaludes-influenced sweatsuit. The Wolf of Wall Street may chronicle of the debauchery of 1980's financial district bros, but this fit is anything but inaccessible. The combination of gray sweatpants, a denim shirt, and white Nike Cortez is so timeless, you've probably worn a fit almost exactly like it sometime in the last week. It just goes to show, it doesn't matter how much money you make, sometimes, you just need to be a cozy boy.

4.Romeo Montague

Film: Romeo + Juliet

Year: 1996

Signature Look: Angst, Personified

Kym Barrett 100% bodied the costume design on this modern reinterpetation of Shakespeare. For centuries, dudes have rolled their eyes in English class thinking Romeo was some punk bitch with a corny hat and stupid tights trying to bang this Capulet chick, then Baz Luhrmann comes along and adds guns, explosions, and John Leguizamo, and all of a sudden Shakespeare becomes awesome. Romeo goes from a pre-LiveJournal sad sack to a troubled gangbanger with a penchant for floral patterns and chain smoking. It was a very visceral way of telling kids "hey, Romeo was like 'Drake' before 'Drake' existed," and the outfits complemented it perfectly.

3.Howard Hughes

Film: The Aviator

Year: 2004

Signature Look: DEFINITELY NOT a Guy Who Pisses In Jars

DiCaprio's Howard Hughes wears the leather flight jacket extremely well, and stands out as one of his best roles ever. He looks stunning in a tux and wore double-breasted suits with pure aplomb. It's no surprise that designers like N. Hoolywood's Daisuke Obana channel him in aviation-inspired fashion collections. In fact, his great style makes his fall from grace more tragic, while his Indiana Jones-esque attire in the film's ending shows that even the most well-dressed man can still be fighting demons underneath his tweed jacket.

2.Jay Gatsby

Film: The Great Gatsby

Year: 2013

Signature Look: The Original New York City Cool Guy

Jay Gatsby predates what Ralph Lauren became. In the same way fashion transformed Ralph Lifschitz to Ralph Lauren, Gatsby uses wealth and style to become his own version of the American Dream. His personal style exhibits his nouveau riche luxe attitude and lifestyle, only wanting the best of the best, whether it came to shirts, cars, or suits. It's no surprise that Brooks Brothers took the helm of the beautifully-crafted menswear in the film, poring through their own archives for the costumes. Author F. Scott Fitzgerald even wore the brand himself. Gatsby's evolution from midwestern farmboy to self-made millionaire is a very hip-hop story that encapsulates just how clothes can really make the man.

1.Frank William Abagnale Jr.

Film: Catch Me If You Can

Year: 2002

Signature Look: Don Draper Plays Dress-Up

Catch Me If You Can's protagonist is a testament to the saying "fake it 'til you make it." Granted, you can probably "fake it" better than others if you're a young white male who looks like Leonardo DiCaprio, as seen in this film. We saw Frank Jr. go from emblem-blazered schoolboy to dapper airline pilot thanks to the help of a peak-lapeled navy blazer and tie bar. He also makes a case for short-sleeve button-down shirts, tortoiseshell eyeglasses, and white pants. That asymmetrical orange cardigan he pairs with tobacco brown loafers? Straight fire. Frank Jr., catch his style if you can.