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100 Most Stylish People of the Last 100 Years

 

Whenever any of your so called ‘style’ journals create a list of the world's most stylish, most usually include people who are, for the most part, included purely because of their sartorial façade, as judged by contemporary mores. But style is a little bit more than just that. It is not restricted to just mere apparel (even though it is a manifestation of other stylish attributes), but is, if nothing else, a state of mind. It is what this formidable index of style-monger - both male and female - concentrates on. Einstein was stylish enough to have a wardrobe full of clothes that were identical, because in his view, outward appearance was immaterial. Frank Sinatra owned a different suit for every day of the year, because to him it mattered. Both had the style to flaunt convention, and more importantly, both had the chutzpah and confidence to pull it off with ease. Those included below are not just those who present-day arbitrators of style consider worthwhile but those, who in their day, were the proverbial cats amongst the pigeons. We have, for the sake of convention, kowtowed to include folk that are predominantly well-known, so what follows is a list of those who resisted the saccharine lure of trends or fashion and were, in effect, themselves, which is what true style is all about. In the words of the late Quentin Crisp: "style is freedom. It is freedom from the need to be competitive, from the need to be fashionable, from the need for "success, from the need for approval. But it is more than simply freedom from".

Such an inventory may well be considered rather trivial and I realize that I am not curing cancer, not feeding the world, not ending world strife. We are, however, providing a smidgen of light relief, alongside a soupcon of postprandial conversation for those that find such tidbits interesting and please remember that this is just my personal opinion and not in any order of preference.

 

Words by Chris Sullivan, images: fameworldface.ru

 
 

 
 

Harry Crosby

The son of one of the richest banking families in New England and the nephew of J.P. Morgan Jr., he’d been an ambulance driver in WW1, saw more death than any 18-year-old should, and was thus, the youngest recipient of the Croix de Guerre in 1919. The undisputed king of excessive American expats in Twenties Paris, Harry, stunningly handsome in that clean-cut, all-American-Brad-Pitt-sense, carried a mop of blonde greased-back hair, sported black suits, black-painted fingernails and a black flower in his buttonhole, while he and his wife, Caresse - a rather well-endowed beauty, who would make today's brightest young reprobates feel distinctly pedestrian. They indulged in spectacular bacchanals, open marriage, seven-in-a-bed-orgies, ominous tattoos, airplane joy-rides, gambling sprees, opiates, cocaine and hashish. But it wasn’t all party-hearty. His Black Sun Press was instrumental in getting the likes of James Joyce, Hemingway and T.S. Eliot to print and he was an avid arts patron. He sadly committed suicide aged 30, in 1929. His final entry in his journal was: "There is only one happiness, it is to love and to be loved”. Progressively stylish.

Sitting Bull

Not only did he lead the Lakota Sioux to defeat and completely obliterate, racist, belligerent warmonger Custer’s Seventh Cavalry, he, so appalled by the squalor of New York and London whilst traveling with Buffalo Bill's Wild West Show, gave away his not inconsiderable earnings to street urchins and the homeless. Stylishly generous. 

Anna Piaggi

The Grand Dame of Italian Fashion, Miss Piaggi, nurtured young talent, influenced the established and always had an irreverent take on style and fashion. Creatively stylish.

 

Jackie Kennedy Onassis

One of the few first ladies to be a downright fashion plate, she popularized big glasses and Hermès headscarves, pillbox hats, low heel pumps, which became known as 'The Jackie Look'. She also campaigned relentlessly to save historic buildings from the bulldozer, such as New York’s incredible Grand Central Terminal and Lafayette Square in Washington, and encouraged Afro-American writers, such as Dorothy West. Influentially stylish.

David Byrne

Born in Scotland in 1952, Byrne married funk with punk, embraced world music, wore huge suits. He has now turned his attention to art, some of which are anonymous public art installations, writing (his latest book is the 'Bicycle Dairies'), and his own internet radio show, Radio David Byrne. He also plays about 14 different musical instruments. Prodigiously stylish.

 
 
 

Rita Hayworth

She began as a dancer, was Astaire’s favourite partner and married Orson Welles and Prince Aly Khan. Always faultlessly dressed, her performance in 'Gilda' is beyond reproach. Dazzlingly stylish.

Frank Sinatra

He sang with style, pulled with style and had his suits made to include miniature pockets - one for his mints to freshen his breath and another for dollar bills to tip the help. Style personified.

John Lennon

When asked if he was a Mod or a Rocker, he replied: "A Mocker!”. Without him, The Beatles proved to be nothing more than sidemen. Frighteningly stylish. 

Cary Grant

Grant couldn't be bothered milking his fame. He liked a nice suit, a cup of cocoa and an early night but still imbibed MDMA and LSD in the Fifties. Stylishly adverse.

 

Tommy Cooper

Apart from popularising the fez, the aesthetically challenged Cooper took the corn out of magic and made it surreal. Stylishly inventive.

 Sugar Ray Robinson

Regarded as the finest ever professional boxer pound-for-pound, he was flawlessly dressed, renowned for his exquisite manners and a great icon for abused Afro-Americans. Massively stylish.

Malcolm Allison

The grooviest football manager ever, he put panache, cigars and big fedoras into the game when it was all sausage sarnies and cups of Bovril. Stylishly large.

Brian Eno

A man who has oozed savoir-faire for years. He influenced a generation of style-mongers and musicians while being both socially and politically intact. Unreasonably stylish. 

David Bowie

A cultural gannet, who has continually polarised trends throughout his career, while evolving artistically. He grew into a cultural giant, a hero to outsiders everywhere. Otherworldly stylish.

 
 

 

Elvis

So iconic he needs only one name. He went from being the sharpest cat on the planet to looking like a fat member of Earth, Wind and Fire, because his tailor in Memphis specialised in clothes for black musicians. Puzzlingly stylish.

Picasso

The man who deconstructed art to just a few lines, was politically correct, casually chic and created a body of work that few have equalled. Stylishly linear.

James Brown

The funkiest man of the last century and not afraid to say so, Brown led the way for black music, in later years had the worst dress sense known to man, but was still rightly known as 'The Godfather of Soul'. Stylishly egotistical.

David Niven

The archetypal suave Englishman abroad, he acted well, wrote two rather amazing autobiographies and managed to don the cravat and not look at all suspect. Stylishly English.

 

DUKE OF WALES/EDWARD VIII

Turn-ups, Aran jumpers, creased trousers, Prince of Wales check, the Windsor knot - the list of his style innovations is endless and to top that, he jacked in his crown. His hobby was to embroider his wife’s underwear. Stylishly regal.

Run DMC

They broke the boundaries of hip hop by bigging up both a style of music and a totally fresh dress sense. Stylishly innovative. 

Alfred Hitchcock

Always wore the same suit, always appeared in his own movies and redefined the thriller. Stylishly perverse.

Bryan Ferry

A debonair, whose suave suits influenced generations and with his unflappably cool Roxy Music said it like it is. Unreasonably stylish.

Lee Marvin

Outshone Brando in 'The Wild One', Glenn Ford in 'The Big Heat', and in 'Point Blank' outclassed the whole acting fraternity. An ex-bomb-disposal-expert, he never took his job seriously and who can blame him. Stylishly unsurpassable.

Fred Astaire

A bit more than a dancer, he was always the picture of elegance, no matter what the occasion - all despite, early in his career, being reportedly described as "not great looking, can’t sing, can dance a bit" by a Hollywood exec. Stylishly reserved.   

Anjelica Huston

Daughter of the mighty John Huston, she was Jack Nicholson’s other half for decades, was a fave model of Helmut Newton and is hep enough never to look a chump at Oscar time. Stylishly aquiline.

 
 

Diana Vreeland

The Grand Dame of international fashion, Vreeland created the fashion shoot, as we now know it, employed great photographers such as Man Ray and Lee Miller, dressed in black and was at times rather reminiscent of a goth even though she was in her eighties. Stylishly severe.

Ava Gardner

Born in a Southern backwater, she started as a model, broke Sinatra’s heart and could out-swear and out-drink most men. As former hubby, Mickey Rooney, said she was "a lady of strong passions, one of them rage”. Stylishly outspoken.

Audrey Hepburn

Born in Belgium of Irish and Dutch parents, Hepburn became a massive Hollywood star known for her impeccable style and manners. Not a great actor, she was the universal epitome of style over content. Stylishly gamine.

Jean Paul Belmondo  

Oozed charisma in 'Á Bout De Souffle', outdid Alain Delon in 'Borsalino', and was magnificent in Claude Lelouche’s 'Les Misérables', YET regarded himself as less than handsome. “Hell, everybody knows that an ugly guy with a good line gets the chicks”, he said. Stylishly Gallic.

Louise Brooks

Starred in some of the Twenties' most daring, erotic, controversial and stylish movies such as G.W. Pabst’s 'Pandora’s Box'. She vogued the ‘bob’ and, at the height of her massive fame, gave it all up, claiming she was bored. Phenomenally stylish.

Marlene Dietrich

Emigrated from Germany to Hollywood, openly criticized Hitler, made the trouser suit fashionable for women and was openly lesbian. Controversially stylish.

Josephine Baker

She danced at the Cotton Club clad only in bananas, walked the Champs-Élysées witha leopard on a lead, and was an active member of the French Resistance and won the Légion d’honneur. Stylishly feline.

 

Edith Piaf

‘The Little Sparrow’ worked her way up from urchin, beggar, prostitute and then street performer to become the greatest chanteuse that France ever produced, always appearing in the same little black slip dress, right up until her premature demise. Stylishly ephemeral.

Billy Holiday

Exuding cool, she was the voice that launched a thousand copycats. She was also an ex-prostitute, a heroin addict and physically abused by her husband. But, still managed to create the most sublime music, retain her dignity and wear orchids in her hair. Languidly stylish. 

Buster Keaton

Trained as a child in vaudeville, whereupon his father would literally throw him across the stage, 'The Great Stone Face' was the ace card in the silent pack, who brought the pork pie hat into vogue. Stylishly brave.

Miles Davis

Limited in range, Miles, still changed the face of jazz. He was stylish to the last, in his three-button Italian-style mohair suits, narrow ties and cropped hair. Epitomizing the cool school of jazz, he thus launched the Mod silhouette. Not an easy man, more an acclaimed genius. Stylishly confrontational.

 

Read more about Stylish People of the Last 100 Years in our 7th printed issue! 

 

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