How do you pin the definition of an icon down? Well, one place to start is timelessness, as it’s virtually impossible to go wrong with keeping things orthodox. Having said that, though, another branch of the tree of iconism would have to be a willingness to step outside the box, managing to stretch its parameters entirely, and setting a new standard. This notion applies to all practices, be it sports, singing, or, in this instance, fashion.
No matter what counter-culture you fall under, it’s hard to argue against the people who lent a hand in shaping the template for menswear — as well as those who continue to bend rules and push the envelope en route to making it all the more open. From traditional tailored formalwear to the patchworked jeans that took the nineties by storm, there is likely someone to thank for making every popular form of attire look cooler than anyone else while setting the standard for what we all want to wear. And in our humble opinion, the 25 men listed below have had a greater impact on shaping classic men’s style than anyone else over the last century or so.
Alain Delon
We’re heading overseas to kick this list off with an extremely appropriate choice. Delon’s blend of upscale taste and sticking to the script is notable in and of itself, the latter of which applies to his archetypal sartorialism as much as it does his acting ability. Keeping things traditional right down to the monkstraps, the French screen legend’s get-up often consisted of oxford shirts, tapered trousers, and a handsome wool coat. His minimalist looks also applied to his casual attire, consisting of plain polos and the occasional chunky sweater. It’s also worth mentioning that he was no stranger to dressing up his wrist, having been seen donning a Cartier Tank time and time again.
Bob Dylan
While the world-renowned artist’s writing style is practically inimitable, the same can not be said regarding his somewhat accessible brand of personal chic. As the same notion may apply to many artists who will appear on this list, Dylan’s wardrobe shifted with age, which is no surprise considering the singer’s eponymous debut was released when he was 21 years old and donning shearling coats. Sure, this may have remained a closet mainstay for Mr. Zimmerman, but what truly comes to mind with the thought of the “Tangled Up in Blue” singer is often a pair of black shades and a leather jacket to match. That said, though, the beauty of it all is his confidence in always wearing whatever he wanted, like effortlessly pairing t-shirts with a blazer.
Brad Pitt
Having served as the epitome of cool for well over three decades at this point, we had no choice but to include the “Once Upon a Time in… Hollywood” star on here. The Oscar-winning actor hones an ability to adapt from one look to another with nothing short of ease, pulling off anything from slouching suits with straightened hair to vintage jackets and making them look ageless. Whether these outfits and accessories appear on the big screen or the red carpet, he’s proven to us just how eclectic his wardrobe can be, right down to Tyler Durden’s unmistakable red shades.
Cary Grant
Whether you’ve seen North by Northwest or not, chances are you’ve seen the outfit in this photo somewhere. Nevertheless, Cary Grant makes an appearance here for far more than his almighty gray flannel suit and legendary sunglasses worn throughout the film. Believe it or not, the actor once came out and said he never considered himself to be much of a style mogul, but his abiding passion for bespoke tailoring and classed-up formalwear refutes that entirely, as the constant Hitchcock collaborator earns this spot for much more than his modesty.
Clint Eastwood
If the thought of versatility was a person, Clint Eastwood would debatably serve as the living embodiment. Actor, director, composer, former mayor, and, last but not least, an unflinching Western shirt lover. There are a variety of distinct looks that you could pinpoint as “classic,” and the Dirty Harry star has managed to pull them off with a staunch sense of unmatched masculinity. Be it a conventional suit and tie or an all-out western get-up, his ability to make the traditional look extraordinary was beyond impressive, right down to his collection of sharp fedoras.
Dapper Dan
Daniel Day’s influence has had a major impact on the consistent logo-plastering we see in the modern age, as he is arguably one of the first people credited for lending a hand to the dawn of streetwear. Aside from his close-knit affiliation with hip-hop pioneers like LL Cool J and Salt-N-Pepa, the informally-dubbed “king of knock-offs” worked his way up the fashion leaderboard upon setting up shop in 1982, years removed from shoplifting garments and selling them for profit. Ultimately, he’s gone from tossing knock-off Gucci logos on his clothing to having a Harlem-based luxury boutique in conjunction with the major label.
David Bowie
In a similar vein to his musicianship, Bowie’s chic was the sheer embodiment of evolution. Based on a sense of unabashed flair and androgyny, the late legend’s gender-fluid wear was emblematic and tone-setting, especially throughout his glamorous Ziggy Stardust era. Managing to impact pop culture from every angle is no easy feat, and the way the shape-shifting singer managed to do so was unlike what few others could even dream of. While many have attempted to channel the openness that Bowie lent a hand in turning normal, no one had the same je ne sais quoi, and it’s safe to say that no one ever will.
Frank Sinatra
As the Rat Pack’s unofficial ring leader, the Chairman of the Board was never afraid to get all dressed up — in fact, he, Dean Martin, and Bing Crosby even have a song called “Style,” so that should say something about how much he cared about staying sharp. From his ubiquitous fedora to his carefree orange knitwear, Frank Sinatra was a man composed of elegance and an added touch of cool, right down to the unfiltered Lucky Strikes that often appeared in his fanciful coats’ pockets.
Gianni Agnelli
Gianni Agnelli’s affinity for looking good was on par with his passion for Italian sports cars, ultimately making him the snazziest person in almost any room. The former Fiat president was often seen dressed in his Sunday best every day of the week, usually wearing the likes of tailored suits crafted by Caraceni, who also made suits for one Mr. Enzo Ferrari himself. In addition to these exorbitant looks, Agnelli’s brand of effortlessness even seeps over to how he wore his tie, tending to keep it off-center as if to show off that he didn’t care about it looked, but he wasn’t fooling anyone.
Gregory Peck
Starring parallel to a female fashion figure like Audrey Hepburn has two results: being entirely overshadowed and being a bit less overshadowed. To the benefit of Gregory Peck and his dashingly well-dressed ways, his role of Joe Bradley in Roman Holiday pulled off the latter with ease. Even more notable than his suit from the 1953 comedy are the round specs he wore as Atticus Finch in To Kill a Mockingbird. As a result, Oliver Peoples recently dedicated a distinct line of sunglasses to them, going to show that his sophisticated style remains as relevant as ever.
James Dean
Serving as a cultural icon has its perks, as the Rebel Without a Cause actor’s unmistakable red blouson speaks for itself in most instances that he, or it, is brought up. With that said, to tie the late talent’s career and sense of style to one single piece would be asinine, in a similar vein to that of Grant and his North by Northwest suit. For his time, Dean’s fashion sense was remarkably trail-blazing, as he managed to set a new standard for teenagers who were tired of looking prim and proper and aimed for a more authentic, rugged look.
Kurt Cobain
Kurt Cobain serves as the archetypal element of the unapologetic grunge trend that primarily ruled the ’90s, and that stands whether the lionized Nirvana frontman would have approved or not. Managing to set the status quo without even trying to do so speaks volumes about how vital he was to the era. However, labeling this a trend would imply that patchworked jeans, band tees, and loose-knit sweaters have gone out of style — believe it or not, this is what makes up a solid chunk of countless contemporary fashion houses’ seasonal collections. Standing the test of time from a music perspective is already impressive as it is, but the need to perform it in front of a massive crowd of people trying to mirror your look makes it all the more unfathomable.
Marlon Brando
What a surprise — another Hollywood star best known for keeping things simple. With Brando’s casual blend of loose-fitting trousers and luxurious leather belts, his look falls in line with many of the minimalist icons who appear on this list, too. As far as his impact is concerned, the literal Godfather had a prominent impact on just how essential the plain white tee has become to one’s wardrobe, managing to prove that nothing is cooler than keeping comfortable. However, his jacket from The Wild One remains one of the more elemental pieces of his on-screen attire, as it’s credited with popularizing the classic leather motorcycle jacket.
Michael Caine
Whether you know him as the one-and-only Jack Carter or as Austin Powers’ father, Michael Caine has unflinchingly maintained his debonair know-how through the years. In the knighted actor’s heyday, he was often seen in double-breasted suits, flashy ties, oversized square-shaped glasses, and even a touch of jewelry. Of all the members you’ll find on this list, you’ll likely find something special that you can notice sooner rather than later, but Caine’s sense of coolness is a bit more difficult to pin down, making him all the more worthy of a spot here.
Muhammad Ali
While you may be more accustomed to seeing the greatest when he was in the ring, Muhammad Ali’s fashion sense outside of it is arguably unmatched. Whether he was wearing a bowler hat to accentuate his pinstripe suit or a silk tie to finish off a twill blazer, he made everything look remarkably effortless, which says a lot about someone who did the very same in his all-timer boxing career.
The Rolling Stones
As masters of debauchery and unabashed decadence, The Stones were as fancifully dressed as they were world-famous, which is baffling to imagine at the peak of their powers. We could sit here all day and talk about how Keith made leopard-clad blazers and silk bow-ties work like no other, or how Mick made ruffled shirts and pink trousers look as manly as anything in the world, but the band’s two mainstays garner enough spotlight as it is. Sticking out like a sore thumb, however, was late drummer Charlie Watts, whose sartorial prowess brought a touch of class to the group that was much-needed through and through. Each respective member’s sprawling wardrobe proves that the Stones truly are men of wealth and taste.
Miles Davis
While his musical style was certainly more unique than his overall look, that shouldn’t diminish the latter in the slightest. With the majority of mid-century musicians tending to keep things traditional from both a sonic and style standpoint, Davis took it upon himself to differentiate himself in both distinct circles, straying away from the plain old black and white tuxedos as he aimed for slim-fitting, Italian-made pinstripe suits. And although the chameleon-like trumpeter had an eye for the avant-garde, he still managed to up the ante on more orthodox wardrobe elements, like high tab collared-shirts and high-top pants — sure, these elements may seem commonplace now, but that is thanks to trailblazers like Davis.
Paul Newman
Paul Newman could just about do it all: act in timeless movies, drive race cars, plaster his face on pasta sauce jars, and, above all else, dress with the best of them. Far from flashy, he stuck to his roots and kept things traditional with a much-needed touch of prep, bringing the two together to provide a hallmark brand of style that has been emulated for years. As a major proponent of penny loafers, single-breasted blazers, and high-waisted trousers, the entrepreneurial legend looked just as fortified in a suit as he did on the track.
Robert Redford
At this point in the list, it’s clear that many elemental members of classic Hollywood had a great eye for sartorial perfection, and Robert Redford is another name that fits the bill better than most. Sure, you may be more familiar with his casual blend of denim jackets and aviator frames, but his devil-may-care elegance sits in the pantheon of fashionable composure, along with major players in the field like the Newman and Brando. Whether preppy, Western, or suited from head-to-toe, there was nothing the Sundance Kid didn’t make look like it was made personally for him, be it mid-filming or off-camera.
Sammy Davis Jr.
As the first Black man to don the cover of GQ back in 1967, Sammy Davis Jr.‘s keen sense of style has never gone unnoticed. While he would tend to stick to the Rat Pack’s typical sharkskin suit when seen on stage, his off-duty attire was just as cool. Primarily composed of button-down shirts and standard-fitting V-necks, the revered performer’s it-factor was noticeable in all circumstances, as he managed to keep things conventional and progressive all at the same time.
Sean Connery
Sure, we could have tossed any Bond actor in here and called it a day, as even the likes of Pierce Brosnan’s Brioni-crafted suits deserve some solid recognition. Be that as it may, none of them boast the same level of unadulterated class, poise, and overall sex appeal as the first 007 to hit the big screen. Sean Connery’s passion for Savile Row-crafted attire remains the standard for all portrayals that have followed suit, and we’d be remiss to not give credit where it is due by acknowledging the initial actor’s luxurious accessories, from his cufflinks to his NATO-strapped Rolex Submariner.
Sidney Poitier
The late, glass ceiling-shattering actor managed to be insanely nonchalant about what he wore consistently, all the while arguably being the most stylish person in any room he appeared in thanks to what we presume were closets filled to the brim with shearling coats and cashmere sweaters. While he was well-kept in a formal scenario, that man also looked great in island-appropriate wear, which comes as no surprise accounting for his Bahamian roots. The ability to pull off a floral button-down and some shades is not something many men would try in his day and age, but he just happened to have the self-assuredness to do so.
Steve McQueen
We could go on and on about the King of Cool, which is why we’ve done so before. Timelessness is the main name of McQueen’s game, having worn some of the modern era’s more quintessential pieces and giving them life quite like few have. Whether it’s the iconic Persol folding sunglasses, the shawl-collared cardigans, or his closet presumably overflowing with Baracuta Harrington jackets, there was virtually no article of clothing he couldn’t pull off with carefree grace.
Tom Ford
As we steer the focus from celebrities and shed a light on the fashion world’s more legitimate moguls, Tom Ford’s work with Gucci, YSL, and his eponymous label is enough to fill up a book — two of them, in fact. The Texas native has described the average Tom Ford customer as “cultured, well-traveled, and possessing disposable income,” and this has been wholeheartedly proven since the luxury label’s conception. From Daniel Craig to Tom Hanks to Jay-Z, countless household names have been seen rocking Tom Ford, serving as a mere showcase of his prominence. But perhaps none have been more impactful than Ford himself, who manages to wear his wares perhaps better than anyone.
Yves Saint Laurent
Rounding this list out is another quintessential name in the world of menswear. The famed French designer has been heralded as one of the most prominent in all of history and managed to do just as much for women as he did for men, having been credited for pioneering the Le Smoking tuxedo suit, which pieced together elements of men’s formalwear and women’s blouses to make for a now-commonplace fashion element. Decades removed from designing the crocodile-embossed leather jacket that hit the runway in 1965, Saint Laurent’s eponymous fashion house remains one of the world’s largest long after his passing, crafting some of the more emblematic pieces in all of men’s fashion and having an outsize influence on the contemporary streetwear scene thanks to the ubiquitous “YSL Aesthetic.”
How to Dress Like Steve McQueen
While every man in this guide has had a tremendous impact on men’s style, arguably no one has had a bigger influence than Steve McQueen. For a detailed breakdown on how to get the late menswear icon’s signature look, have a look at our guide on how to dress like the King of Cool.
