Smooth Criminals: The 25 Most Stylish Law-Breakers in Movie History
In honor of the 40th anniversary of A Clockwork Orange, we've rounded up the sharpest-dressed crooks, killers, and authority-defying scoundrels to ever hit the big screen
By Sean Fennessey, Andrew Richdale, and Mark Byrne
Photo: Everett Collection
25. Danny Ocean (George Clooney), Ocean's 11
George Clooney dresses down the Rat Pack look for a new generation by losing the tie, but everything else about his style in this film is pure Hollywood A-list. It's not about a guy named Danny Ocean, just like it wasn't back in the 1960 original with Frank Sinatra; it's about how boss Clooney is. And even when he's unwinding by the craps table, his style nails that.—Mark Byrne
Photo: The Kobal Collection
24. Marcel (Pierre Clémenti) Belle de Jour
In this Luis Buñuel art-house classic, Marcel, a gritty, bullet-popping thug, wins the affections of the most alluring mademoiselle in the brothel, a head-spinningly sexy Catherine Deneuve in her prime. We don't know what Clémenti did after this was filmed. But we can safely say he is the only Frenchman ever to pull off a leather jacket, cane, and gold teeth without a hitch.—Andrew Richdale
Photo: Courtesy of Screen Gems
23. Ghost (T.I.), Takers
Here's the truth: This is not a good movie. But all of the guys in it—Hayden Christensen, Idris Elba, Chris Brown, and especially T.I.—look like they were given full reign to raid the racks at Bergdorf. There is even—we shit you not—a montage scene at a men's store. So, credit where it's due.—M.B.
20. John Dillinger (Johnny Depp), Public Enemies
The real Dillinger, with his mop of thin black hair and smarmy smirk, was not a handsome man. But he was always perfectly dressed, an urbane thug. Depp was too pretty for the role, but just smoldering enough to pull off the look: flat-brimmed fedora, heavy wool overcoat, three-piece suit, and rip-roaring Tommy gun.—Sean Fennessey
22. Sebastian Valmont (Ryan Phillippe) Cruel Intentions
For those of a certain age, this was a defining film—a campy riot about blue-blood problems, getting anything you want, and sex. Phillippe's Sebastian was the head WASP in charge and mastered a specific, hard-to-master art: looking like you deserve to be in the driver's seat of a vintage Jag. Of course it helps having Upper East Side money to blow on those lux-y suits and turtlenecks. In his defense though, he looked just as entitled when he ditched the threads to seduce the unconquered virgin, Reese Witherspoon—who just so happened to be his future off-screen babe. –M.B.
21. Tony Montana (Al Pacino), Scarface
Pacino spends a good deal of Scarface counting cash, snorting coke, and shooting anything he damn well pleases, but his wardrobe is pure class—especially his trim, classic tus. One notable exception we feel compelled to point out: the massive, lapel-swallowing collars so common in the '70s. We consider those a failure of the era though, not Pacino.—M.B.
Photo: Courtesy of Focus Features
19. Jack Twist (Jake Gyllenhaal), Brokeback Mountain
It's Montana in 1963. Shacking up with another cowboy won't be legal for another 34 years. It takes guts, to say the least. In shearling jackets, properly-matched denim, and, of course, a Western hat, Jack Twist dresses the part of a rugged fella willing to break all sorts of social and literal laws. The real style is in the way Twist pulls his clothes on though—consciously. Even self-consciously. His insecurities come out in the way he bundles his hands in pockets and lowers his hat's brim. He makes those tics look covetable though, even if his situation isn't.—A.R.
18. Tyler Durden (Brad Pitt), Fight Club
In Fight Club, Tyler Durden is the narrator's mental projection of perfection—a scheming assailant of consumerism. He's the most badass thing director David Fincher could imagine. To look the part, Durden is dolled up in leather and couldn't-give-a-fook-less tanks; he smokes like a chimney; and the icing on the cake? Blood, buckets of it.—A.R.
17. Arthur (Joseph Gordon-Levitt) Inception
Even though Leo's every bit the leading man in this film, JGL knocks it out of the park in the style department. His principle expertise: dominating a three-piece suit. Breaking one up isn't for the faint of heart. But then neither is zero gravity pistol matches nor incepting a powerful CEO's most well kept secret.—M.B.
16. Tom Ripley (Matt Damon), The Talented Mr. Ripley
Identity theft—ain't it a bitch? Ripley not only tries to steal the life of Dickie Greenleaf (Jude Law), but he also kills his best friend. Strolling the Amalfi coast with bold-framed glasses, throwback suspenders, and loosened oords, he rubs it all in by looking better than his victim, too. —A.R.
14. Frank Abagnale Jr. (Leonardo DiCaprio), Catch Me If You Can
It happens from time to time: You see a guy who is somehow able to crush an otherwise tired uniform. It's tricky, but so is being a con man, like the chameleonic Frank. He pulls it off by taking his undercover costumes to the next level with non-regulation tie bars, tortoiseshell frames, and crisp white pocket squares. Dressed like this, there's not a thing the guy could say we wouldn't believe.—M.B.
15. Michael Corleone (Al Pacino), The Godfather Part II
There's no suit out there more powerful than a double-breasted, and Michael Corleone is sort of the cinematic ambassador of its reputation. Other reminders that you can have someone whacked at the drop of a hat: smooth ascot-sports coat combos that are Early Vegas in just the right way.—M.B.
13. Jules Winnfield (Samuel L. Jackson), Pulp Fiction
The original BAMF. With a straight-up GQ suit and 'fro, Jules' get-up screams, "I'm Not Fucking Around Here." Which is the ideal message to send if your line of work involves pointing a gun and quoting Ezekiel.—M.B.
12. The Devil (John Cassavetes), Rosemary's Baby
There's a rumor about this movie, that the Devil himself cursed it. Why? Because John Cassavetes looked that damn good channeling him. It's quite a feat pissing off the Big Man down under, and he pulls it off with the aid of impeccable khaki suits and turtlenecks that are every bit as evil as they are suave. —A.R.
11. Jesse James (Brad Pitt), _ The Assassination of Jesse James_
Pitt's James is a taciturn character, nearing the edge of his outlaw life with regret and frustration. But after dozens of robbed banks and trains, he's certainly mastered a kind of debonair veteran criminal look: three-piece suit, chained pocket watch, strong braided belt, and no tie. He doesn't need one when he's already got the ultimate accessory: a pair of six-shooters on the waist. –S.F.
10. Danny Ocean and Crew (Peter Lawford, Dean Martin, Sammy Davis Jr., Frank Sinatra), Ocean's 11
Low-buttoned suits, high-banded shirts, ties as skinny as one inch—these are the well-thought touches the original Ocean's gang used to accent to their heist back in 1960. It made their punches look stronger, their frames look taller, and their demeanor tougher than the new guys. Sorry, Clooney. —A.R.
7. Clyde Barrow (Warren Beatty), Bonnie and Clyde
These days, bank robbers really don't put any effort into the art of it all. Sure, a ski-mask is more utilitarian, but look no further than Beatty's Clyde Barrow, playboy extraordinaire and supreme wearer of a fedora, for how it ought to be done: tweedy vests and buttoned high shirts. The tie is optional, stunning arm candy is not.—M.B.
Photo: Courtesy Warner of Bros. Pictures
9. The Joker (Heath Ledger), The Dark Knight
Looking deranged takes no skill. Looking deranged and stylish takes genius. You match your hair to your three-piece suit—your green and purple suit, the one with odd geometric patterns and a sick trim fit. And to edge ahead of the other peacocks strutting their stuff in Gotham, you add a lot carefully smudged make-up. It's the perfect touch of crazy for the Why-So-Serious icon.—A.R.
8. Jack Carter (Michael Caine), Get Carter
The challenge faced by costume designer Evangeline Harrison was contrasting Michael Caine's sophisticated gangster style with the local fashion of Newcastle, the hardscrabble town he arrives in to avenge the murder of his brother. Her solution was to bring Caine to the legendary '60s tailor Dougie Hayward for a fitting. "Dougie's suits were almost '30s in their cuts," says Harrison. "Quite high-waisted. They flared over the hips a little." The suits created a look that was both sophisticated and menacing, perfect for a film whose stark display of sex and violence led one critic to compare it to "a bottle of neat gin swallowed before breakfast."
6. Agent Smith (Hugo Weaving), The Matrix
But this look is so simple, right? True, but how often have you seen a potato sack black suit and fat ole black tie. Nothing wrong with simple when you kill the details. Even doing light-speed backflips, Agent Smith and his carbon copies keep their tie bar perfectly straight and shades in check. If only every robot looked as GQ as Agent Smith.—A.R.
5. Renton (Ewan McGregor), Trainspotting
Before Pete Doherty popularized strung-out chic (again), a Scottish cad did it and did it well. McGregor's Renton makes everything from hooligan sweaters and fake leather jackets to torn jeans and cheap polyester suits look like a loud, resounding statement: I do Heroin.—A.R.
4. Mr. Blonde and co. (Michael Madsen, Tim Roth, Harvey Keitel, and Steve Buscemi), Reservoir Dogs
A great suit is nothing without the right accessories and finesse. This crew knows no wrong though. Mr. Blonde deftly loosens his tie, giving it just the right amount of room. Mr. White keeps his jacket buttoned, no matter what. Mr. Orange kicks his game up a notch with a pair of ass-kicking Clubmasters. And they all carry enough lead to send anyone who questions their decisions six feet under. –M.B.
3. Kit (Martin Sheen), Badlands
Martin Sheen's roaming, murderous outlaw is based on true-life killer Charles Starkweather, who famously resembled James Dean. Sheen told GQ, "James Dean had a profound effect on me when I was a boy, and it's not a bad idea to act like your hero until you become yourself." Thus, the Canadian tudo-ed Sheen, all ambling disaffection and boiling fury, carries a cool all his own.—S.F.
2. Patrick Bateman (Christian Bale), American Psycho
Patrick Bateman operates in a world overrun by douchey power suits and statement ties. It's not saying much to be the best-dressed guy in that crew, but he's more than that. He slays the competition by dressing the part of the finance bro in the best possible way: his contrast collars are crisp, his hair perfectly slicked back, his high-end suits expertly tailored. What's more? The man expertly wields a badass accessory: an a.—M.B.
1. Alex DeLarge (Malcolm McDowell), A Clockwork Orange
Eggiwegs! Look who 'tis up top? Droogmaster Alex DeLarge. He's the leader of a band of rape-friendly, amoral menaces. We shouldn't aspire to look like him. But, 40 years later, we still do, all of it down to the codpieces. (Just not sure where we'd wear all of it.) We wanted some clarity on what the hell it is he's actually sporting—and the story behind it, because looks this maniacally awesome never come with out one—so we talked to McDowell himself. Here's the skinny on one of the most head-scratching get-ups in history:
"I told Stanley [Kubrick]: 'I've got cricket gear in the car.' 'Let's see it,' he said. 'Put it on.' And then he goes. 'What's that?' 'Why that's my cricket protector.' 'Well, wear it on the outside,' he tells me. So the whites were literally my cricket gear. He had been thinking about a codpiece anyway, because he liked the sort of Medieval feel. The costumier brought a large selection of hats and had the bowler in mind for me. It represented the city, the establishment, respectability and all of that. Then, I found a yard of eyelash. I showed it to Stanley as a joke. And he said, 'Great, wear it. But just on one eye, you hear?'"—A.R.
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