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The 10 Most Stylish Movies Of All Time

January 26th, 2024

Style Inspiration From The Silver Screen

Films are amazing, aren’t they? Time machines. Style books. Escape pods. We draw a lot of our style inspiration from the characters we see in films. For many, a classic film may be the first introduction to the world of menswear and style. A well tailored suit, a leather jacket, a plain white t-shirt – any of these may adorn a character in a movie and stick with us. It becomes an obsession. We want to look like that.

Here are our picks for 10 of the most stylish movies of all time. They have certainly helped shape the opinions of style for decades.


The Thin Man (1934)

Nick and Nora Charles are the heroic style couple we need more of in our lives. William Powell’s dashing retired – but somewhat un-retired – private detective is featured in this 1934 Oscar-nominated film which was so well received that it spawned five follow-up features.

“The Thin Man” is a master class in 1930’s style and high living as it follows Powell’s character through luxury cross-country trains and holiday parties wearing immaculately tailored suits, tuxedos, classy two-piece pajama sets, and formal top hats.

An interesting note is that Powell supplied his own suits for the film which was not uncommon in Hollywood at the time. This leaves little room for doubt that Powell was every bit as stylish and dashing in real life as his sartorially superlative detective persona was on film.

Nick Charles exemplified the idea of the gentleman in the 1930s: Classic style featuring sharp lines and flattering cuts paired with conservative accessories. Nick was always dressed for the occasion.


Wall Street

Gordon Gekko. The name itself is enough to conjure up images of sharp tailoring lines, high contrast color combinations, and precious metal cufflinks and watches. Oliver Stone’s ruthless Wall Street pirates almost cartoonish style soon became synonymous with 1980s menswear and strayed away from caricature into aspirational.

Much of the film, set in New York, features stylishly dressed professionals but Gekko casts a long sartorial shadow over everyone else. His contrast shirt collars and braces are arguably the most memorable features of his style. So much so, that it is likely impossible to wear those items in public without at least one person referencing the films antagonist.

“Wall Street” left an indelible mark on the 1980s. It is not only a well-made film that has stood the test of time, but it thrust tailored menswear right into the center of the public consciousness again. In fact, it’s not a stretch to say that a generation of men who came of age when this film was released probably view business dress through the lens of Gordon Gekko.


Reservoir Dogs

The black suit is a divisive topic in menswear these days. Is it too stark? The right or wrong choice for a first suit? For an only suit? Questions abound and debates continue but one thing that absolutely cannot be denied: Quentin Tarantino certainly made them look cool in his debut film “Reservoir Dogs.”

The well-dressed gangster and master heist man is a trope that never gets old and the crew in “Reservoir Dogs” plays it up as iconically as possible. Slim lapels, skinny ties, and dark shades evoke an almost 1960s dangerous spy vibe that works well in the realm of of diamond thieves.

In this film, the black suit lends a lot of gravity to the gangsters living in them. There is an effortless cool combined with a seriousness that they embody while wearing something as stark as a black suit. “Reservoir Dogs” took suits out of the exclusive domain of law offices and boardrooms and put them in the closet of sharp witted and violent diamond thieves in the L.A. underworld.


North by Northwest

Alfred Hitchcock’s late-1950s spy thriller may be the peak of gentleman style. Cary Grant epitomizes looking cool and feeling comfortable in a suit. His class just jumps off the screen. If anyone was ever born to wear a well-tailored suit, it was almost certainly Cary Grant.

Grant’s Roger Thornhill is Don Draper meets James Bond. He’s a Madison Avenue executive who is mistaken as a spy. Thornhill could be seen as the sartorial template for both Don and 007 as in nearly the entire film, he is seen wearing a flawless gray Glen plaid single breasted suit, a crisp white dress shirt, gold cuff links, oxblood cap-toe oxfords, a dark tie, and a covetable Cartier Tank. In short, the perfect recipe.

Grant’s witty dialogue and deadpan delivery add to the overwhelming style of the film. Nearly every aspect of “North By Northwest” has aged well from the plot, to the dialogue, to the stunning menswear. It is truly a timeless cinematic achievement.


The Thomas Crown Affair (1968)

I’m fairly confident that Steve McQueen’s middle name was “cool” but please don’t fact check me on that. McQueen’s cool credentials are on full display in 1968’s “The Thomas Crown Affair” where he plays an impossibly stylish millionaire businessman who is also a criminal mastermind that executes the perfect heist.

Mr. Crown’s exploits are all accomplished in style. We see him in expertly tailored three-piece suits, casual Harrington jackets, Persol 714s with blue lenses, and an iconic blue windbreaker that, quite honestly, maybe only McQueen himself can pull off.

The casual elegance that McQueen sells in “The Thomas Crown Affair” is set against the backdrop of a jazz-infused late 1960s score, intrigue, and subterfuge. This is another the example of a film where the anti-hero is so stylish, you might think you missed your calling as a dapper, wealthy, suave businessman who masquerades as a bank robber.


The Talented Mr. Ripley

Being transported to 1950s Italy to experience a rich night life and outdoor cafes in fine Italian-designed tailoring isn’t something that current time and space technology will allow. However, the 1999 film “The Talented Mr. Ripley” gives us a glimpse into what we might have to look forward to (or back to?) once time machines are available for purchase.

The titular character, Matt Damon’s Tom Ripley, is somewhat conservatively dressed with heavy, boxier cuts associated with Ivy League uniforms of the time. The true style star of the movie is his foil, Dickie Greenleaf. The American ex-pat hiding out in Italy is played to perfection by Jude Law and he exudes the very essence of 1950s Italian style.

Summer ready peak collar short-sleeved shirts in beautiful knits are the iconic looks from the film and this is part of Dickie’s personal uniform. He excels in the causal department which plays into his character’s desire to absolve himself of any real responsibility and enjoy the laidback Riviera lifestyle.

Particular attention was paid to the clothing to ensure it was time-period correct. So if you’re looking for some late-1950s Riviera style inspiration, give “The Talented Mr. Ripley” a viewing. It’s the closet thing we have to a time-machine.


American Gigolo

In 1980, Armani made a film called “American Gigolo.”

Okay, that’s not factually accurate but maybe not too far off. Richard Gere’s character in this classic film is seen almost exclusively in tailored Armani clothing and it shows. His character has influenced men’s style from the moment the film hit theaters.

The classic “men want to be him and women want to be with him” certainly applies here. The look that is perhaps most associated with the film is Gere in shirt and tie with a camel overcoat. The image graced film posters and promotional materials and no doubt caused a worldwide shortage of the garment. All of a sudden men who never even considered a dressy overcoat couldn’t imagine navigating a conversation with the opposite sex without one.



It’s no accident that the impossibly cool Steve McQueen would be mentioned on this list a second time. This film has so much style, it is frankly impressive that director Peter Yates was able to fit it all into a single movie. Iconic car chase? Check. King of Cool? Check. A Lalo Schifrin score? Double check. The cool doesn’t end there.

The iconic car chase scene from “Bullitt.”

If we are being honest with ourselves, at no point in history has a navy turtle-neck sweater looked as great as it does on Steve McQueen in this movie. He wears this sweater with charcoal pants and a brown tweed sport coat that creates a color palette of somber but pleasing combinations. Without the jacket, we see the absolutely iconic image of McQueen’s Frank Bullitt with a gun-holster over the sweater – an image so striking that it may or may not have been emulated by one Roger Moore several years later in “Live and Let Die.”

Frank Bullitt has become a style icon over the years for a single outfit that is casual, well thought out, and versatile. In short, he’s achieved peak style.


The Great Gatsby (1974)

The Roaring 20s is a time lauded for its glamour, style, and unique attire that has influenced nearly everything that came after it. We associate it with grand parties, formal wear, and carefree lifestyle. While that certainly was the extent of the decade, we owe our associations of this time in large part to the stories written by one of the greatest American authors of all-time – F. Scott Fitzgerald.

The 1974 film adaptation of his best-selling novel is a tour-de-force of 1920s style. Scenes taking place during the summer days feature light and brightly colored three-piece suits in lightweight fabrics such as linen while evening scenes at the glamorous Gatsby estate parties are filled with tailored evening wear.

The film harkens back to a time when men seemed to take their clothing a bit more seriously. Attire was more thought out and intentional for each specific occasion. Gatsby and his guests put on their modern-day suits of armor when mingling with each other. Jay Gatsby – portrayed expertly by Robert Redford – was always put together without a hair out of place. “The Great Gatsby” is a remarkable look at 1920s New England summer style.


Three Days of the Condor

If you weren’t expecting a second Robert Redford film right after the previous, well, shame on you. Redford is a style icon and his follow up to 1974’s “The Great Gatsby” was the espionage thriller “Three Days of the Condor.”

Similar to other films on this list, the film features an on-the-run protagonist who sports an iconic outfit for the bulk of the film. Robert Redford’s CIA-agent, code named “Condor”, is easily the most casually dressed character in this list however his outfit is every bit as iconic.

The film follows Condor on his chase through Washington D.C. after his office mates in his CIA research team are eliminated. While we most think of CIA agents in stark, dark suits, Condor’s team is undercover and dressed as such. He sports slim-fitting jeans, a blue Oxford shirt, a sharp navy sweater, and an all-purpose gray herringbone sport coat. He looks like an average guy in Washington D.C. – except he’s Robert Redford, so that’s really not fair.

The casual style he portrays is perhaps one of the most approachable looks on this list and that is certainly part of why this look has been imitated for decades after the films release.

Stylishly Yours,

Logan Morford

Logan Morford is a Communications Director in Lexington, Kentucky. His interest in menswear really took off in his late 20s as his career necessitated a more polished look for meetings and travel. His work, combined with a healthy love of James Bond and the idea of the gentleman spy, serves as the inspiration. He lives with his beautiful wife who instilled the idea of fashion being able to evoke emotion when she gifted him with a vintage engraved OMEGA. They both love getting dressed up for date nights to remind them of when they were first dating, and hope to instill this love of classic fashion and civility into their young daughter.

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Edited by Rachel Butler

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