10 Most Stylish Movies

If you haven’t noticed yet, I love movies, and I love fashion. This week I went ahead and combined the two. Take this as your list of the next ten movies to watch, or take this as where to get your style suggestions. Go crazy. Happy #MillenialFriday folks. Love you.


1. Ocean’s Eleven (2001)

It’s George Clooney and Brad Pitt in suits. What more do you want? And remember buzz cut Brad Pitt? He rocks. A few standout notes come to mind. Pitt’s character wears these disgusting silk shirts all the time, and they are perfect. This is wear your personal style becomes a strength. If you can display your personality through your outfit then it’s a good thing to wear. Those silk shirts aren’t something any of us with taste would wear. But a Las Vegas conman? He spends his time in opulent Vegas casinos, only living on cash he scrounges together. That is his idea of wealth. It’s perfect. Also, Clooney is in a suit in the entire trilogy and rarely has a tie on. That became a trend that I’m willing to say he started. The rest of the characters, similar to Pitt, are over the top. They indulge in the Vegas lifestyle. This movie says so much about who the character is using only their clothes. Matt Damon, who is the last to join the gang is much more understated, because he’s new to this Vegas thing. Elliott Gould, who has been there the longest, is literally wearing rose-colored glasses.

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2. To Catch a Thief (1955)

Hitchcock’s crime caper that is set in the French Riviera brings the likes of Cary Grant and Grace Kelly. With two co-stars as beautiful as this, it is difficult not to have them look fashionable regardless of what they are wearing. A good portion of this movie could be considered rich people porn. Nice houses, nice cars, nice clothes all set on the luxurious waterfront of the South of France. Kelly dons the dresses of a socialite and looks stunning. Hitchcock’s nod to the geographic region is what stands out. Grant looks impeccable in his suits throughout, but it’s really his French nautical sweater that stands out and oozes style. Your style is your own, but a "when in Rome" approach can pay dividends.

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3. The Devil Wears Prada (2006)

This may be the most important fashion movie of all time. Based on an intern’s experience working for the most revered name in fashion, the dictator of taste, Anna Wintour, The Devil Wears Prada is a Vogue look book from start to finish. (Stanley Tucci looks great too!) While the movie’s fashion is definitely persuasive, it’s actually Meryl Streep’s speech about fashion that lands it a spot on our list. In a mere monologue, she pinpoints what it is about the fashion industry that values it at well over a billion dollars and how it affects the lives of us all. That speech says more about the movie than I could write. Powerful stuff, check it out: 

‘This… stuff’? Oh. OK. I see. You think this has nothing to do with you. You go to your closet and you select… I don’t know… that lumpy blue sweater, for instance because you’re trying to tell the world that you take yourself too seriously to care about what you put on your back. But what you don’t know is that that sweater is not just blue, it’s not turquoise. It’s not lapis. It’s actually cerulean. And you’re also blithely unaware of the fact that in 2002, Oscar de la Renta did a collection of cerulean gowns. And then I think it was Yves Saint Laurent… wasn’t it who showed cerulean military jackets? I think we need a jacket here. And then cerulean quickly showed up in the collections of eight different designers. And then it, uh, filtered down through the department stores and then trickled on down into some tragic Casual Corner where you, no doubt, fished it out of some clearance bin. However, that blue represents millions of dollars and countless jobs and it’s sort of comical how you think that you’ve made a choice that exempts you from the fashion industry when, in fact, you’re wearing the sweater that was selected for you by the people in this room from a pile of stuff.

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4. Crazy, Stupid, Love (2011)

Another very fashionable movie, but it’s on our list because of its discussion about fashion. Ryan Gosling’s character alone puts this movie in the conversation. He’s in suits and sweaters and tees. He wears everything so well. But he goes above and beyond. He takes Steve Carell under his wing. Clothes make the man is a very harrowing piece of advice. What you choose to wear isn’t only how the world sees you. You are telling the world how you see yourself. Gosling takes Carell and shows him the essentials every man should have in his closet, to demand better. Even more, he shows how to totally revamp a pathetic wardrobe into something respectable all for only roughly one credit card limit. We watch a man who is completely lost in his own billowing khakis begin to dress with intention and getting the respect of others, by first respecting himself.


5. Clueless (1995)

I’ve been talking (and will continue to talk) a lot about menswear and capital “F” fashion a lot. To be completely honest with you, I don’t even remember what the men are wearing in Clueless. I know for sure that Paul Rudd is in it, because he’s Paul Rudd. But every time I watch this movie, I’m captivated by whatever Alicia Silverstone is wearing. The yellow tartan plaid skirt and jacket is a revelation that has been replicated by countless Halloween costumes and a chart-topping music video. Each scene Silverstone’s Cher is wearing something that has had a lasting impression on fashion, especially in the high school demographic. It is a great film with even greater clothes. I mean, I don’t know. Just go watch Clueless.

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6. Lords of Dogtown (2005)

Dare I say, the genesis of street style. In today’s world of fashion, the sidewalk is as influential as the runway. We have brands like Supreme, a skate shop, worth a billion dollars and collaborating with Gucci. This is just a movie about skateboarding and the skaters just look cool. That’s all there is to it. The navy blue Zephyr skate team shirts are some of the coolest tees ever, but beyond that, it’s California guys looking awesome. Heath Ledger gives a sensation performance as a drunken surf hippie, so check the movie out for its acting chops on Ledger’s part. An often-overlooked part of style is grooming. Your hair can play just a big a role on your personal style as your clothes, and Lords of Dogtown is loaded with bleach-blonde Cali surfer dreamboat hair. It’s great. Wear cool clothes and get ya hair right.

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7. Reservoir Dogs (1992)

This is a simple, as bare bones as it gets. It’s five guys in black suits with white shirts and black ties. This is menswear minimalism. If you are a hypebeast that needs something over the top, this movie also has Chris Penn in a velour tracksuit to satisfy your thirst. The lore of the move gives loans itself to its importance. As the story goes, Tarantino didn’t have a costume budget so he had the cast wear the one thing they all already had in their closets, black suits.


8. Drive/The Place Beyond the Pines (2011/2012)

I mentioned Ryan Gosling earlier but this is really, where I get to wax poetic. He wears nice clothes. He’s a movie star, of course he does. But one thing he does better than any of his fellow celebs and display how the fit of clothes matter much more than the amount you spend on them. I don’t know if there has been a piece of costuming in cinema history with more swagger than the jacket in Drive. It’s a white bomber jacket with a scorpion on the back. From here on to forever will there be kids Google-ing that jacket after they watch that movie. Conversely, in The Place Beyond the Pines, Gosling bleaches his hair platinum blonde, dons face tattoos, and wears a cutoff Metallica shirt and looks equally like a model. The over-sized tour merch become a look, perfected by Kanye, but Gosling started it with this movie.


9. Romeo + Juliet (1996)

You can read all the style guides you want. You can follow all the rules laid out for menswear, but style isn’t style until you add your personal affectation. I, personally, dress like a bad Baz Lurhman character. I would fit just as well in The Great Gastby as I would in Romeo + Juliet. That said, my personal style guru is very much, 90’s Leo DiCaprio crying out to the heaven’s in an opened Hawaiian shirt. It’s an iconic scene and an iconic look. Leo has played the gentleman. He has walked the red carpet. Hell, he is J. Gatsby. We know he can wear a suit. He showed his star power when he dressed down and looked just as good.

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10. The Talented Mr. Ripley (1999)

Another one of the most beautiful casts ever assembled, The Talented Mr. Ripley is picturesque with it’ 60’s Italian Riviera backdrop. The characters wear suits, sweaters, loafers, and thick-rimmed glasses. Also, the movie could be mistaken for a sunglass commercial. SO. MANY. SUNGLASSES. This is very traditional and can show you how timeless good style can be. The movie is set 50 years ago and throughout you see oxford blue button ups, navy polos, boat shoes, and other pieces that are just as common today. Fashion fades. Style is forever.


There you have it! Like, comment, share, max your credit card on some new jawnz. I would love to hear your favorite style movies. Or your favorite movies. Or your source for your style. Or questions about mine. Tweet with #MillenialFriday to start the conversation.

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