Fashion inspiration is everywhere, as long as you’re looking. Sometimes you don’t even have to look too hard, because it’s projected 30 feet high on the cinema screen. Though you may have missed your chance to see these in the theatre, the 15 Most Stylish Movies Of Modern Time are still just as fashionable on the small screen. Special thanks to the D’Marge Facebook community for their help in compiling this list.
Stylish Movie #1 – A Single Man (2009)
Easily the most voted for by the D’Marge community was A Single Man. Tom Ford stepped behind the camera for the first time to direct A Single Man. While some doubted his directorial chops, no one doubted that his characters would be well dressed. The film turned out to be a visual masterpiece, owed in large part to Ford’s simple, refined, cool costume choices.
Stylish Movie #2 – The Untouchables (1987)
This is the flick that made Armani. The Untouchables stars Kevin Costner, Robert De Niro, and Sean Connery, so you already know it’s going to be awesome. Add in Giorgio Armani’s incredible period costumes and you’ve got a fashionable film that’s become the stuff of legends.
Stylish Movie #3 – Crazy, Stupid, Love. (2011)
If nothing else, Crazy, Stupid, Love. deserves credit for making green suits and talking with your mouth full look cool. Ryan Gosling is pretty much the epitome of big screen style these days, and this film does not disappoint. Fun fact: many of his suits were designed by The Strokes guitarist Albert Hammond Jr. for L.A. boutique Confederacy.
Stylish Movie #4 – Skyfall (2012)
Any list about fashionable modern movies would be incomplete without James Bond. Skyfall saw Daniel Craig looking his Bond-y best in custom Tom Ford. Costume designer Jany Temime meticulously designed the suits, then sent them to Ford who dispatched Italian tailors to make each piece by hand. It’s good to be Bond.
Stylish Movie #5 – The Talented Mr. Ripley (1999)
The fashions of The Talented Mr. Ripley were inspired by the Italian seaside and classic preppyness. The doubleheader of Matt Damon and Jude Law makes for one of the most stylish casts of all time, inspiring wardrobe envy across the world. We certainly don’t blame Tom Ripley for wanting a piece of Dickie Greenleaf’s life and the wardrobe that comes with it.
Stylish Movie #6 – Ocean’s Eleven (2001)
Ocean’s Eleven famously served up some of the best dressed criminals around. Brad Pitt’s suits alone would be enough to earn the movie a spot on this list, but he’s far from the only stylish man in the film. It’s definitely not every day that a bunch of crooks look this good when they’re up to no good.
Stylish Movie #7 – Alfie (2004)
Jude Law makes another appearance on the list, this time for teaching us that buying well-made clothes on the cheap can be a good thing. In the remake of the Michael Caine classic Alfie, Law plays a dapper specimen with a fondness for scarves, blazers, Vespa scooters, and beautiful women.
Stylish Movie #8 – American Psycho (2000)
American Psycho is the film that reminded us how cool the 80s were (and changed the way we listened to Huey Lewis and the News for evermore). Patrick Bateman’s killer style (oh yeah, I went there) has become legendary. It also seems to be the inspiration for the vast majority of Scott Disick’s wardrobe.
Stylish Movie #9 – Casino (1995)
Casino is badass Las Vegas gangsters at their best, including their best dressed. They say that clothes make the man…in this case, clothes make the mob. De Niro and the rest of the cast looked flawless from start to finish, in costumes that were mostly built from scratch with a few vintage pieces thrown in.
Stylish Movie #10 – Drive (2011)
The Gos delivers again with Drive, in which he single handedly brought back the parachute jacket and driving gloves. There aren’t a lot of different looks in Drive, but it doesn’t matter. The iconic scorpion jacket, inspired by a Kenneth Anger video and made custom by Richard Lim of High Society, is now a part film fashion history.
Stylish Movie #11 – American Gigolo (1980)
Armani did it again in American Gigolo, this time with Dickie Gere. The film put Armani and Italian fashion on the map in the 80s, and word has it Gere was so taken with his sharp American Gigolo wardrobe that he has worn almost exclusively Armani designs onscreen ever since.
Stylish Movie #12 – The Business (2005)
Starring Danny Dyer, Tamer Hassan, and Roland Manookian , The Business follows the rise and fall of a young man’s drug importing career on the coast of the Costa del Sol in Spain. Epic Sergio Tacchini tracksuits and old Porsche 928s made this film a standout. It should also be noted that female lead, Georgina Chapman, is now one of the hottest women’s fashion designers.
Stylish Movie #13 – Blow (2001)
This is a movie about Johnny Depp and Pee Wee Herman making the most of drug money by buying up a killer collection of luxury houses, cars, and women…what’s not to love? Of course, there’s also the wardrobe of leisure suits and long-collared shirts, which only a man with the swag of Depp could possibly make so cool.
Stylish Movie #14 – Layer Cake (2004)
If you like your mercenaries badass but well dressed, and have a soft spot for the Audi RS6 Wagon, Layer Cake is the film for you. Daniel Craig rocked his looks in this movie from start to finish, but the most coveted are his leather jacket and impeccable off-white suit.
Stylish Movie #15 – The Great Gatsby (2013)
Ok, so technically this one isn’t out yet, but by all accounts it promises to be one of the most fashionable flicks of the year. The soon to be released Baz Luhrmann take on The Great Gatsby, starring Tobey Maguire and Leonardo DiCaprio, promises to be uber stylish – just check out the trailer!