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Frank Sinatra – Infamously irreverent, the black and white images of Sinatra do no justice to the rich colour palette of his wardrobe which included pink, lavender, and particularly orange. But when the sun went down, it was only ever black tie - or midnight blue, at a stretch. -
Bryan Ferry – As the singer for new wave band Roxy Music and later as a solo musician, Ferry’s personal style mimicked his career’s evolution. Sequins, satin and animal prints were left behind for the smooth perfection of three-piece suits in Ferry’s signature blue. -
Yves Saint Laurent – As a designer, Saint Laurent broke many of fashion’s long-held rules, an attitude that was reflected in his personal style. The iconic glasses, the hair and foppish elegance created the look of a legend. -
George Clooney – Clooney’s old Hollywood sense of style belies his affable nature. A gentleman to the end, Clooney is evidence that great style is achievable at any age. -
James Dean – The rebellious actor had a reputation for pushing boundaries, both on screen and in style. His defiantly urban style paved the way for the likes of Brad Pitt and Ryan Gosling. -
Steve McQueen – The epitome of laid-back cool, McQueen was a pioneer when it came to mixing high-end clothing with casual details. A fan of Persol eyewear, the actor even had a range sunglasses named after him. -
Sidney Poitier – Sir Sidney’s aesthetic can be summed up in one word: dignified. During the Civil Rights movements, Poitier could be easily spotted in the crowd with his slim-cut tailored black suits and black tie. -
Nick Wooster – Stylist and photographer’s favourite at Pitti Uomo, Wooster has been praised for reinvigorating modern menswear. Shorts suits, luxury sneakers and heritage brands, Wooster perfectly mixes street cred with high end tailoring. -
Cary Grant – One of Hollywood’s definitive leading men, Grant was as famous for his award-winning roles as he was his classic, relaxed aesthetic. A fan of English tailoring, Grant described his style as that of a "well-dressed, sophisticated chap". -
Jared Leto – Leading the way for modern men, Leto’s experiments with style have ranged from grooming to suiting. Not one to shy away from sartorial risks, Leto has that inner confidence to make even the most outlandish outfit look cool. -
Errol Flynn – Despite a lifestyle that suggested the contrary, Flynn’s personal style favoured reserve. The Australian-born actor was also very aware of the importance of good grooming. -
Robert Rabensteiner – L’Uomo Vogue’s fashion editor has become a fixture in best dressed lists for his eye-catching sense of style. The heavy beard, layered draping and preference for broad-rimmed hats are instantly recognisable. -
Fred Astaire – Tiepins deliberately worn askew, slim-cut sleeves on his suit jacket and a tie worn as a belt, Fred Astaire was the master of subtle quirks. Despite the physicality of his performances, Astaire was never anything less than pure sartorial perfection. -
Warren Beatty – Infamously assumed to be the subject of Carly Simon’s hit, You’re So Vain, Beatty had good reason to be so. Whether it was silk scarves and suede jackets or clean-cut in a blazer, Beatty was the right mix of Ivy League and international lothario. -
Alain Delon – French actor Delon was considered such a quintessential representative of refined Gallic style that he was made the face for French label Christian Dior’s iconic cologne, Eau Sauvage. -
Omar Sharif – The late Egyptian-born Sharif had a cosmopolitan sense of style. His saturnine looks were in stark contrast to the Hollywood standard of the times. -
Michael Caine – Part cad, all gentleman, Sir Michael was rarely seen in anything but the finest suits. A fan of British tailor Douglas Hayward, Caine embodied refined good taste even during the flashy 60s. -
Gianni Agnelli – Dubbed the Godfather of Style, the former head of Fiat was infamous for his subtle nuances such as watches worn over the shirt cuff and hiking boots with bespoke Caraceni suits. -
Jean-Michel Basquiat – Known for wearing Armani suits splattered with the paint from his work, American artist Basquiat’s personal style was as brash as his paintings: slightly eccentric, yet with an acute eye for detail and texture. -
David Gandy – The Scottish male supermodel is known for his combinations of statement pieces and old-school suits. Signature looks include belted cardigans, a fondness for hats and mismatched suiting. -
Mick Jagger – The Stones front man has been a pioneer when it comes to pushing the boundaries of menswear. Skinny jeans, androgyny – you name it, Jagger’s done it. -
Andre Benjamin – Better known as Andre 3000, Andre Benjamin knew the importance of a scene-stealing look. Despite some early mishaps, his interpretation of Ivy League prep made suspenders cool again. -
Serge Gainsbourg – In every way a libertine, Gainsbourg’s rakish sense of style was only every outdone by his reputation as a scallywag. Never one to follow rules, the singer was infamous for eschewing socks and ties with his three-piece suits. -
Pep Guardiola – While soccer fans might disagree on Guardiola’s success as coach at Bayern Munich, the Spanish-born footballer is known as the most stylish bloke on the sidelines. Photo: Getty Images -
Hunter S. Thompson – There’s no mistaking the fact that gonzo journalist and author Thompson had a unique sense of style. The combination of bucket hat, Hawaiian shirts, Converse sneakers and Aviator shades were the cornerstone of his wardrobe. Photo: Supplied. -
George Best – Before David Beckham there was George Best, an English footballer whose off-field style was as famous as his ball skills. The Northern Irish native embodied the experimental hedonism of the '60s with a working class charisma. -
Tinie Tempah – Nigerian-born rapper Tempah has mastered the panache required for winning red-carpet looks and sophisticated street-style. Tempah’s secret? Offset bolder statement pieces with classic staples. -
David Hockney – The man thought to have brought the English Dandy aesthetic to the US, Hockney’s sense of style is as timeless as his art. In his later years, he became infamous for his deliberate clashing of colours and prints. -
James Coburn – A career built playing the archetypal tough-guy, Coburn’s off-screen style was more nuanced, and what he dubbed as 'elegant wolf' attire consisting of blazers teamed with silk polka dot handkerchiefs. -
Javier Bardem – While Bardem may not be as groundbreaking as others on this list, the Spanish actor is testament to the truth that classic staples can never go out of style. -
Tom Ford – Consistently voted the most stylish man in the world, the very name Tom Ford has become synonymous with luxury. Stubble with velvet smoking jackets, black tie without the actual tie – Ford has not so much broken style rules as as he has rewritten them. -
Malcolm McLaren – The father of punk, McLaren revolutionised Britain’s fashion and music scenes. The driving force behind turning street wear into a political statement, McLaren’s own style was an eclectic mix of traditional tailoring and avant garde. -
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What makes a stylish man? Is it the immaculate cut of his suit on the red carpet, or the way he carries off sharp fashion on the street?
Gore Vidal once said that great style is an attitude; about knowing who you are and what you want. Or, in other words, not giving a damn.
This kind of chutzpah explains why men such as Jared Leto, Nickelson Wooster and Fred Astaire are placed near the top of the list whenever the question of style is floated.
Mitchell Oakley-Smith, editor at menswear magazine Manuscript, says the most stylish man in the room is often the one who is the most simply dressed.
"Sometimes there's nothing more stylish than a navy blazer or a white button-down shirt or a grey suit," Oakley-Smith says.
"But putting it together well, having it well cut and made and pressed – those sorts of details elevate a fairly traditional and common garment to something innately stylish."
All about attitude
You see, whether it was Astaire's off-beat accessories, Wooster's penchant for tailored jackets with shorts, or Leto's ambiguous androgyny, what makes these men stand out is not so much what they wore but rather how they wore it.
So with that in mind, we've created what we believe is a definitive list of the most stylish men from the past 70 years.
While some have made a name for themselves thanks to their reputation for the unconventional (think Andre 3000), others (like Javier Bardem and George Clooney) make the cut thanks to their unwavering good taste.
From the timeless taste of Cary Grant to the novel prints favoured by Hunter S. Thompson, these men have led the way when it comes to sartorial expression.
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