15 Must-Watch Movies For Menswear Inspiration

Cinema has a larger influence on the way we dress than we may give it credit for. There’s nothing like the big screen to show clothes in the right situations, worn by characters we can look up to. And sometimes, movies that really go the extra mile in the wardrobe department can make a lasting impression on our style.

The following movies are excellent examples of this. Each of them has clearly paid attention to the costume design for its characters, such that the menswear is actually a stand-out component of the film on its own. These movies have dressed their characters so exceptionally that they’re also worth bookmarking as references for style.

The James Bond Franchise
The original menswear icon, and perhaps still the most widely-acknowledged, is James Bond—few would question that. And while Sean Connery’s Bond will always be the most stylish, one can still make a case for each of them. (Even Daniel Craig!) And because the franchise has been consistent with this aspect of the character, Bond is still the first-to-mind well-dressed man in cinema, even after all these decades.



The Kingsman Franchise
Both Kingsman movies are modern riffs on the James Bond franchise that took all the established spy film tropes and turned them on their heads. One way they did that was to project Bond’s iconic stylishness through the lens of modern menswear, which meant that they were able to exaggerate that aspect of the movies: the Kingsman organization’s front is a tailor shop, all the Kingsman spies are suited to perfect measure, and the first movie even made a catchphrase of “Oxfords, not brogues.” Knowing that menswear is a burgeoning mainstream culture that more and more men can relate to, they doubled down on the cool clothes.


The Man From U.N.C.L.E. 
This 2015 reboot of a Bond-era spy series was also a feature-length homage to classic men’s style. The entire movie looks like a series of magazine editorials or an Instagram blog for aspirational men’s lifestyle. Every aspect is covered: crisp outfits, cool vintage cars, expensive hotel rooms, a mustached antagonist, and of course, the beautiful Alicia Vikander. In The Man From U.N.C.L.E., Henry Cavill plays Napoleon Solo, an American spy who must work with Armie Hammer’s Ilya Kuryakin, a Russian spy, to prevent a nuclear war. Throughout the movie, the two also represent different kinds of well-dressed: Solo wears clean, Americana-style suits, while Kuryakin wears more laidback, Euro-chic outfits.

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North By Northwest
One of Alfred Hitchcock’s later works involved Cary Grant wearing a gray suit while on the run from agents of a mysterious organization who mistakenly believe he is someone else. But more importantly, that gray suit. It captured the ideal fit of its time and was of such a perfect monotone gray that it became as iconic as the movie itself.



The Graduate
Despite all the male fantasies that The Graduate indulged its audiences in, the clothes still managed to stand out. Sure, there’s Mrs. Robinson—but also, look at Dustin Hoffman’s white pinstripe blazer, and his perfectly cut slim trousers. Look at how well he pulled off the blazer-and-jeans look. In fact, the main character is never not well-dressed throughout the whole movie—except maybe in that scene with the wetsuit.


Breakfast At Tiffany’s
Audrey Hepburn’s little black dress may be the sartorial star of this movie, but it also made a case for slimmer ties and lapels on casual suits—and, well, casual suits in general. George Peppard’s entire ensemble is full of enviable menswear maneuvers: a simple gray two-piece suit, a cardigan under a tweed jacket, a red striped tie with a navy blazer. Breakfast At Tiffany’s is not just a rom-com; it’s a masterclass in prep dressing.


The Thomas Crown Affair
Steve McQueen is an unimpeachable style icon, and he was hardly ever more stylish in any of his movies than in The Thomas Crown Affair. In it, McQueen plays a millionaire-sportsman-criminal mastermind who clearly has a taste for fine clothes. He makes several cases for the three-piece suit throughout the movie, which also popularized the Persol Model 714, now one of the most iconic sunglasses in modern menswear. Though the 1999 incarnation in Pierce Brosnan—then also James Bond—also played it very, very cool, the original is still the best.



In The Mood For Love
Wong Kar-Wai’s 2000 film is often considered to be the greatest work of Asian cinema to date, cited for its unique aesthetics and incredible cinematography. But the film’s visual mood-setting also lent itself to the stylishness of its lead character, played by Tony Leung, whose sharp suits look even better against the film’s backdrops. In the movie, Leung also rocks a slicked-back hairstyle that’s 15 years ahead of the one you asked the barber for last week.


Get Carter
You may know him as Bat-Bale’s Alfred or Austin Powers’ fah-jah, but in his heyday, Michael Caine played some pretty stylish lead roles. The navy blue three-piece he wore as Newcastle-born gangster Jack Carter in Get Carter is as classic and as timeless as it gets, but the real style move in this film is the shotgun. It just pulls the whole outfit together.


American Gigolo
The clothes in 1980’s American Gigolo may not fit the style standards of today, but at the time, it was the greatest fashion editorial that Giorgio Armani could ask for. Large suits, broad shoulders, wide-legged pants, double-collared polo shirts—these came to define the menswear of the ’80s: Italian tailoring with bombastic American proportions. Another interesting reason to watch this movie: its score was composed by Giorgio Moroder.



A Single Man
Let’s just say Galahad isn’t the most stylish character that Colin Firth has played. Back in 2009, he starred in a movie directed by none other than Tom Ford (yes, that Tom Ford—so you know its characters are well-dressed). Firth plays a depressed gay English professor who struggles with his loneliness, but somehow always looks like he walked straight out of a Saint Laurent runway.


An alarmingly thin Jake Gyllenhaal plays a mean-spirited crime beat journalist in Nightcrawler—the kind of character you’d love to hate as you deconstruct him throughout the film. And while the outfits here seem more incidental, you’d definitely notice the character’s camp collar shirt (which, three years after the movie’s release, is now one of the hottest menswear trends), the Clubmaster-style half-frame sunglasses, and the grey New Balance M996.


This Steve McQueen classic will always be best-known for the dark green Mustang, but the clothes here are also worth remembering. Few other movies have made a better case for wearing brown: the blazer and the trench coat that McQueen wears here are certainly style moves to steal.



Ocean’s Eleven
The Clooney-led reboot doesn’t hold a candle to the original Oceans Eleven, which starred five of the Rat Pack: Peter Lawford, Frank Sinatra, Dean Martin, Sammy Davis, Jr. and Joey Bishop. Seeing these guys in well-tailored suits puts Brad Pitt’s collar-out look to shame. And let’s not even talk about Don Cheadle’s disco-into-the-2000s outfit.


The Talented Mr. Ripley
We talk about Italian style and sprezzatura quite a bit when we talk about menswear, but few films have embodied them better than The Talented Mr. Ripley, in which Matt Damon plays a serial impersonator who’s out to steal another man’s life. The film is shot almost entirely in Italy, and shows incredible Italian coastal style that you’d want to cop for your next vacation (whether or not you’re actually going to Italy).

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Miguel Escobar
Assistant Features Editor for Esquire Philippines
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