A List of 25 Men’s Fashion Icons You Would Love to Know

Define an icon. Start with timelessness, as it’s hard to go wrong with tradition. Iconism also requires a willingness to venture outside the box, stretch its parameters, and set a new standard. This applies to athletics, singing, and fashion.

No matter your counter-culture, it’s impossible to argue against those who helped shape menswear and those who continue to bend boundaries and push the edge to make it more open. Someone made every popular kind of apparel look cooler than anybody else, setting the benchmark for what Teeanime all desire to wear. The 25 men below have influenced classic men’s style more than anybody else in the last century.


We start with an appropriate international pick. Delon’s premium taste and script-following are renowned, and the latter extends to his sartorial archetypes as well as his performance. The French screen legend wore oxford shirts, tapered pants, and a wool coat with monkstraps. His casual outfit included basic polos and bulky sweaters. He often wore a Cartier Tank on his wrist.


While the world-famous artist’s writing style is distinctive, his personal chic isn’t. Dylan’s wardrobe changed with age, which isn’t surprising considering his debut album was published when he was 21 and wearing sheepskin coats. The “Tangled Up in Blue” vocalist is generally associated with black sunglasses and a leather jacket. The beauty is his confidence in wearing whatever he chose, like t-shirts with blazers.


The “Once Upon a Time in… Hollywood” star has been the embodiment of cool for nearly three decades. The Oscar-winning actor can switch from slouching suits to antique coats with ease. He’s shown us how diverse his clothing can be, down to Tyler Durden’s crimson shades.


If you’ve seen North by Northwest, you’ve probably seen this outfit. Cary Grant is here for more than his gray flannel suit and sunglasses. The actor recently said he never considered himself a style mogul, but his affinity for bespoke tailoring and formalwear refutes that. The Hitchcock collaborator earned this slot for much more than his modesty.


Clint Eastwood is the personification of flexibility. Former mayor, actor, director, composer, and Western shirt fan. Dirty Harry hero has pulled off several “classic” looks with unequaled machismo. His ability to make the customary look remarkable, down to his collection of snappy fedoras, was beyond impressive.


Daniel Day’s influence has led to the continuous logo-plastering we see today. He is credited with helping to launch streetwear. The “king of knock-offs” made his way up the fashion leaderboard after establishing up shop in 1982, years distant from shoplifting and reselling clothes. He went from wearing knock-off Gucci emblems to opening a Harlem boutique with the company.


Bowie’s chic embodied development, like his music. His gender-fluid attire was iconic and tone-setting, especially during his Ziggy Stardust heyday. The shape-shifting singer’s ability to influence pop culture from every perspective was unmatched. No one has ever had Bowie’s je ne sais quoi, and no one ever will.


As the Rat Pack’s unofficial ringleader, the Chairman of the Board was never afraid to dress up. He, Dean Martin, and Bing Crosby even have a song called “Style,” so that should say something about how much he cared about looking smart. Frank Sinatra was elegant and stylish, down to the unfiltered Lucky Strikes in his coat pockets.


Gianni Agnelli’s love of fashion and Italian sports cars made him the sexiest man in any room. The former Fiat president wore clothes by Caraceni, who also produced suits for Enzo Ferrari. Agnelli’s effortlessness extended to how he wore his tie, which he kept off-center to imply he didn’t care, but no one was fooled.


Paralleling a fashion icon like Audrey Hepburn might make you completely or partially overlooked. Gregory Peck’s portrayal as Joe Bradley in Roman Holiday suited his dashingly well-dressed manner. His big glasses as Atticus Finch in To Kill a Mockingbird are perhaps more memorable than his suit from 1953. Oliver Peoples just dedicated a line of sunglasses to them, proving his subtle style is still relevant.


As a cultural symbol, James Dean’s crimson blouson speaks for itself whenever he, or it, is mentioned. Comparing the late talent’s career and style to Grant’s North by Northwest suit would be absurd. Dean’s fashion style was ahead of its time, setting a new standard for teens who wanted a more real, raw look.


Kurt Cobain represents the uncompromising grunge trend that dominated the ’90s, whether he agreed or not. He was so important to the era that he set the status quo without attempting. Labeling this a trend would imply that patchworked jeans, band shirts, and loose-knit sweaters are out of style. Standing the test of time in music is impressive, but doing it in front of a huge throng of imitators is unimaginable.


Another basic Hollywood star! Brando’s casual mix of loose-fitting trousers and rich leather belts matches many minimalist icons on this list. The actual Godfather made the basic white tee a style staple, proving that comfort is stylish. His jacket from The Wild One popularized the iconic leather motorcycle jacket.


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’s style outside the ring is unparalleled. He made everything look effortless, which says a lot about someone who accomplished the same in his all-timer fighting career.


The Stones were masters of excess and blatant indulgence, which is hard to imagine at their zenith. Keith made leopard-clad jackets and silk bow-ties work like no other, and Mick made ruffled shirts and pink pants seem manly, but the band’s two constants get enough attention. Charlie Watts’ sartorial prowess offered the band much-needed polish. The Stones’ vast wardrobes suggest they’re wealthy and tasteful.


His style was more unique than his look, although that shouldn’t be discounted. Most mid-century musicians kept things traditional from a musical and style standpoint, so Davis sought for slim-fitting, Italian-made pinstripe suits. The chameleon-like trumpeter had an eye for the avant-garde, but he also upped the ante on more conservative clothing pieces, such high tab collared-shirts and high-top slacks.


Paul Newman could act in timeless movies, drive race cars, and dress well. Far from flamboyant, he stayed classic with a hint of prep, creating a signature style that has been copied for years. The entrepreneurial icon favored penny loafers, single-breasted jackets, and high-waisted trousers.


Robert Redford is another iconic Hollywood actor known for his impeccable style. His devil-may-care grace ranks alongside Newman and Brando in the pantheon of fashionable composure. Nothing the Sundance Kid wore didn’t look like it was made for him, on- or off-screen.


As the first Black man to grace the cover of GQ in 1967, Sammy Davis Jr.’s style has been noted. Off-duty, he wore a cool version of the Rat Pack’s sharkskin outfit. The revered performer’s it-factor was obvious in all circumstances, as he managed to maintain things traditional and progressive.


Even Pierce Brosnan’s Brioni-made suits deserve some respect. None of them have the class, poise, and sex appeal of the original 007, however. Sean Connery’s penchant for Savile Row-crafted clothes sets the standard for all representations that have followed suit, and we’d be foolish not to acknowledge his luxury accoutrements, from his cufflinks to his NATO-strapped Rolex Submariner.


The late actor who broke glass ceilings always looked like he didn’t care what he wore, even though he was probably the most stylish person in any room he walked into because his closets were probably full of shearling coats and cashmere sweaters. Even though he was well-dressed for a formal event, that man also looked great in island clothes, which shouldn’t be a surprise given that he was from the Bahamas. In his time and place, not many men would wear a floral button-up shirt and sunglasses, but he was confident enough to do so.


We could talk about the King of Cool for hours, which is why we have. McQueen’s main goal is to make clothes that can be worn at any time. He has worn some of the most iconic pieces of the modern era and given them life in a way that few other people have. Whether it was the famous Persol folding sunglasses, the shawl-collared cardigans, or the Baracuta Harrington jackets that must have filled his closet, there wasn’t much he couldn’t wear with effortless style.


Tom Ford’s career with Gucci, YSL, and his eponymous label could fill two books — and has. The Texas native has defined the normal Tom Ford consumer as “cultured, well-traveled, and wealthy,” and this has been verified since the luxury label’s founding. From Daniel Craig to Tom Hanks to Jay-Z, many celebrities have worn Tom Ford, showcasing his popularity. No one wears Ford’s clothes better than he does.


Another menswear icon completes our list. The famous French designer accomplished just as much for ladies as he did for men, pioneering the Le Smoking tuxedo suit, which combined men’s formalwear and women’s blouses. Saint Laurent’s eponymous fashion brand is one of the world’s largest decades after he designed the crocodile-embossed leather jacket in 1965. It crafts some of the most iconic pieces in men’s fashion and has a huge influence on streetwear thanks to the “YSL Aesthetic.”