The men who get it just right
Messrs Sam Lambert and Shaka Maidoh
If their job description is hard to define (try reading Mr Maidoh's entry in our Style Council directory), the dress sense of the Art Comes First duo is equally hard to pin down. It's a very contemporary take on menswear informed by every genre of black music from the last hundred years, from the suits of blues musician Mr Robert Johnson to the punk-reggae look of Bad Brains. Jazz, however, seems to be the dominant influence when Messrs Lambert and Maidoh create their clothes (they are essentially designers and stylists), which is why we refer to their style as 21st-century hard bop.
Monsieur Yves Saint Laurent
Now that the late French designer's brand is under the direction of Mr Hedi Slimane, and going from strength to strength in a quite different guise, it's easier to judge Monsieur Saint Laurent's enviable personal style. It's also intriguing, given that our era is dominated by Italian influences, to look back to a time when France was responsible for the last word in relaxed elegance. The enduring influence of Monsieur Saint Laurent, who died in 2008, is such that his rumpled cotton double-breasted suit, with its patch hip pockets and wide lapels, would have wowed the street-style photographers at the Pitti Uomo fashion fair this summer, and any summer.
Mr William Faulkner
The author of 20th-century classics The Sound and the Fury and As I Lay Dying wasn't just notable for his stream-of-consciousness literary style. His neat snow-white hair, salt-and-pepper Donegal tweeds and extravagant moustache epitomise the look of mid-century men of letters. Sadly his heavy drinking also corresponded to type. Aside from the pipe, the thing that most obviously dates the shot is the evident weight of Mr Faulkner's tweed suit, which looks to be radically thicker than anything made today. We also admire the formal, double cuffs on his shirt and the pocket square that echoes the colour of his hair, although the thought that misguided hipsters will feel emboldened to affect pipe-smoking is a worry. Better to interpret Mr Faulkner's look in a more casual way by wearing unstructured tweed jackets this winter.
Signor Walter Bonatti
These days Italian style broadly breaks down into two parts - either flashy designer chic or the elaborately tailored look of the Pitti peacocks. So the image of the late author and explorer Signor Walter Bonatti, shot in Cormayeur after his 1964 attempt to scale Mont Blanc, is a revelation. Tanned and slightly unkempt, his appearance is refreshingly simple thanks to the rugged plaid shirt and the canvas straps of his backpack. Signor Bonatti didn't just look the part, he was a serious climber and made the first wintertime solo climb of the north face of the Matterhorn. He was also a romantic and a purist in his approach to mountaineering, which he defined as "victory over your own human frailty". One could say much the same thing about dressing well.
Mr Leroy "Satchel" Paige
What does it say about the peerless elegance of the 1930s that baseball player Mr Satchel Paige looks more like a hip jazz musician than an athlete? The spear-point collar on his shirt and the loosely cut sleeves on the suit might give away the fact that Mr Paige was a follower of fashion, but the appeal of his clothes has endured even longer than his 40-year career as a pitcher, first in the Negro Leagues and then in MLB. He was famously cocky and charismatic - qualities that his outfit seems to eloquently project. A man's clothes should tell his story, and be relatively honest about it.
Mr Leonard Cohen
No, it's not the star of The Graduate. It's the Canadian singer-songwriter best known for "Hallelujah", a song that's been much covered, most notably by Mr Jeff Buckley. In recent years Mr Cohen has been quietly competing with Rolling Stones drummer Mr Charlie Watts for the title of the best-dressed gentleman in rock; he told his biographer, Ms Sylvie Simmons, "I was born in a suit." While Mr Cohen now does seem to live in a suit, in this shot from the early 1970s he's sporting a casual outfit that would still be ideal for a stroll in the park. The chunky rollneck is as relevant today as it was back in 1972, while the trench coat is worn casually in a way that's now unusual, but which relates closely to the garment's military heritage and informal origins.
Count Simone Rucellai
No one likes to be put in a box, but if a man must submit to a label then Tuscan aristocrat is surely one of the best. In the 30 years since this shot was taken, Count Rucellai has had to sell his mansion, Villa Triboli, so let's remember him as a young man proud to be the owner of a powerful BMW motorbike. The subtle appeal of his perfectly cut tan suit contrasts with the eye-catching helmet which, given the care that's gone into the count's hairstyle, seems unlikely to make it onto his head. We like the way that Mr Slim Aarons framed the shot with the building's three arches, but we admire the dark shade of the count's brown shoes even more.
Mr Aristotle Onassis
The late Greek shipping tycoon demonstrated that the combination of good taste and a great tailor (in his case the legendary Caraceni of Milan) are sufficient to overcome any physical imperfections that God bestows upon a man. Mr Onassis' elegance should bury forever the old myth that big men should avoid double-breasted suits, something that undoubtedly relates to his jacket's low buttoning point and the four-by-two or Kent button stance. It's said that the tycoon always wore a black tie because he believed the consistency ensured his clothes gave away nothing about his mood. Whatever the reason, the result is admirably simple - neo-dandies should take note. NB: this shot was taken in Paris, where Mr Onassis bought his famous statement spectacles from Bonnard and from François Pinton.
Mr Lucien Freud
Given their visual facility, it's unsurprising that many painters are snappy dressers. Mr Freud, one of the greatest British artists of the past 60 years, was no exception. In later years he wore a grey scarf so frequently it become something of a trademark, and he's also said to have had a penchant for extraordinarily expensive leather jackets from French luxury brand Zilli, but this shot from the 1950s speaks more directly to modern tastes - not least because of the way photographer Mr Cecil Beaton faithfully recorded the peeling paint on the wall in the background. Mr Freud's slim sweater and the sporty stripe on the side of his trousers lend his outfit a very contemporary air. While his style is worth emulating, his intensity is surely unrepeatable.
Mr Mark Ronson
This deejay, musician and record producer, best known for his work with the late Ms Amy Winehouse, has long been interested in clothes, but as he matures he's looking increasing well put together and less obviously showbiz. Perhaps it's the influence of his French wife, Ms Joséphine de la Baume, but the neat haircut, tailored trousers and simple blue blazer worn casually with a T-shirt are really working for him. They certainly beat the self-consciously youthful look he used to sport. Mr Ronson, like many men, looks his best when he's wearing tailored clothes in a way that makes it entirely clear he's not going to be spending the day in an office. Look no further for inspiration if you're dressing for a night out.
The Kennedy brothers
Their style legacy may not be as important as their political legacy but President John F Kennedy, Senator Robert F Kennedy and Senator Edward Kennedy remain the poster boys for sophisticated East Coast Ivy style. Their soft-shouldered suits are an inspiration for office wear, their tweed jackets an inspiration for weekend wear, and their swim shorts set the pace for beachwear.
Mr Dave Brubeck
The late Mr Dave Brubeck is a jazz icon, and the man behind Time Out, the genre's first million-selling album. As a star of the genre with the best-dressed musicians, Mr Brubeck needed to look good, something he initially achieved in soft-shouldered suits and skinny ties. However, and perhaps as a result of his Californian upbringing, he also had an affection for more casual styles, such as this vividly printed shirt.
Mr Dennis Hopper
The actor and photographer appeared in, and in some cases directed, the films that defined the cinematic image of the 1950s, 1960s, 1970s and 1980s. As you'd expect from a man who appeared in Rebel Without a Cause, Easy Rider, Apocalypse Now and Blue Velvet, Mr Dennis Hopper was keenly aware of the importance of creating the right look, whether with the perfect olive bomber jacket, or a great convertible.
Mr George Hamilton
These days Mr George Hamilton is best known for the depth of his perma-tan, but look beyond the teak-oil façade and you'll see a man with an unswerving devotion to dressing well. He was a customer of London's late celebrity tailor Mr Douglas Hayward, and still retains the firm grip on classic style that he's been demonstrating for more than 50 years.
Mr Howard Hughes
Fearless and pioneering aviator, engineer of genius, film producer and lover of beautiful women including Mses Katharine Hepburn, Bette Davis, Ava Gardner, Ginger Rogers and Gene Tierney, the vastly rich Mr Howard Hughes had it all. And to top if off he also had an excellent sense of style, and looked as suave in softly tailored jackets and suits as he did purposeful in leather flying jackets and fedora hats.
Mr Alex Turner
The singer from Arctic Monkeys has come a long way from the 20-year-old who collected the 2006 Mercury Music Prize in a charcoal long-sleeve T-shirt and jeans. His current 1950s-inspired image (part biker, part teddy boy, part Elvis) became apparent at his band's appearance at the opening ceremony for the 2012 Olympic Games, and the result is as successful as their superb 2013 album, AM. He also knows how to smarten up when the occasion demands it.
Mr Johnny Carson
The idea that a chat show host could offer sartorial inspiration seems outlandish in 2014, but US television legend Mr Johnny Carson knew how to dress, and showed this over the 30 years he anchored The Tonight Show. Nearly half a century after he made a habit of wearing odd jackets with dark trousers it once again looks very relevant.
Mr Vittorio De Sica
Born in the Lazio region of Italy, Mr Vittorio De Sica grew up poor, in Naples, and remains a poster boy for the city's distinctive tailoring. Although he's best known for the neorealism of films such as Bicycle Thieves, he dressed like a gentleman in suits cut for him by Mr Vincenzo Attolini, the tailor at Mr Gennaro Rubinacci's shop London House. While his clothes were faultlessly formal, they also ensured that he looked entirely at ease, a combination that was, and remains, powerful.
Mr Warren Beatty
The Hollywood actor and director has combined a commercially and artistically successful career in the movies with five decades of political activism, and, at least until his 1992 marriage to actress Ms Annette Bening, a reputation as a prolific lover of beautiful women. Whether long-haired in a denim jacket or, as here, clean-cut in a sports jacket, he's always known how to dress with relaxed sophistication.
Mr Jamie Hince
The British guitarist, whose biography is curiously obscure given that he's married to one of the most beautiful women in the world, has been making records, first with Scarfo and now with The Kills, for the past 20 years. His dedication to rock'n'roll has never been in doubt, and his style reflects this. With his skinny jeans, winkle-picker boots, striped T-shirts and black leather biker jackets he reminds us that rebellion can be chic.
Mr Aaron Young
Born in San Francisco, but now based in New York, Mr Young is an artist who is represented by the Gagosian Gallery, and has shown at New York's PS1 and Whitney galleries, as well as the Serpentine and Saatchi galleries in London. His style varies between an exemplary take on classic Americana, in the form of work boots and well-worn double denim, and more dapper ensembles involving well-tailored black tuxedo jackets. What doesn't vary is his enviable (and presumably carefully cultivated) hairstyle.
Mr Peter Beard
This highborn New Yorker is the art world's answer to Mr Ernest Hemingway, having been inspired by Ms Karen Blixen's book Out of Africa to dedicate much of his career to recording his travels of the continent in the 1960s and 1970s. Dapper when out and about in New York, Mr Beard's style really clicks when he's in Africa, and dresses with a Bohemian air, mixing Western clothes with native Kenyan dress. In this photograph we admire how his attitude takes all the formality out of a military coat.
Mr Serge Gainsbourg
This late French singer was a man who seemed to sum up the notion of roguish Gallic charm. His good living - he smoked, drank and behaved with abandon - was legendary, and his sense of style correspondingly louche. As such he set a fine example for men who want to make tailoring their own, as he demonstrates here in a three-piece pinstripe suit worn without a tie or socks, but with his favourite white Repetto dancing shoes.
Mr George Lowe
A member of the famous 1953 British Mount Everest Expedition, which saw Sir Edmund Hillary and Mr Tenzing Norgay reach the summit of the mountain, Mr Lowe was a New Zealander whose role in the expedition was to direct the documentary films. While archive shots of Mr Lowe in a suit reveal he knew very well how to dimple his tie, he looks far more at ease reminding us that men started to wear goose-down jackets in order to be able to conquer the planet's most inhospitable terrain.
Mr Bobby Gillespie
The lead singer of British rock and dance band Primal Scream has maintained an admirably consistent approach to style over the 30 years since he first stepped on stage in Glasgow, Scotland. Inspired by the classic rock look of The Velvet Underground, Mr Gillespie continues to wear slim jeans, Chelsea boots and long hair even now that he's celebrated his 50th birthday. In this shot he also wears an eye-catching printed shirt with aplomb.
Mr Johnny Hodges
This Bostonian saxophonist was called "The greatest man on alto sax I ever heard" by legendary bandleader Mr Benny Goodman. And like many jazz musicians Mr Hodges had a talent for dressing that rivalled his talent for playing. His look varied from the generously cut suits of the 1940s to more Bohemian styles in later decades, but he was never better dressed than when in this textured double-breasted suit. The way he wears it with patterned socks, braces, an open-neck shirt and a cocked fedora is exemplary.
Mr Marlon Brando
In the 1950s, a decade that saw him nominated five times for the Best Actor Oscar, Mr Brando redefined the craft of acting, and what it meant to be a star. While his performance in 1953's The Wild One was arguably his most influential from a style perspective, creating the enduring biker look, it's his blue-collar clothes in On the Waterfront that really chime with this season's rugged, workwear-inspired outerwear. Mr Brando's casual style has things to teach men even if the closest they'll get to the waterfront is stepping onto their yacht.
Mr Robert Rabensteiner
Rarely do men in the fashion business transcend their role behind the scenes to become icons in their own right, but L'Uomo Vogue's editor in chief Mr Rabensteiner is increasingly in demand in front of the camera. He's renowned for mixing sophisticated soft tailoring with casual jeans, and introducing bold solid colours to his outfits. With these techniques he brings a modern attitude to fairly classic forms, something he deftly achieves with this three-piece midnight-blue dinner jacket.
Mr Humphrey Bogart
He might be best known for the white tuxedo he wore in Casablanca, or Sam Spade's rumpled suits in The Maltese Falcon, but in Tokyo Joe Mr Bogart played an ex-serviceman who returns to the Japanese capital after WWII in search of his wife, and his old businesses. The drapey suits Mr Bogart wears in the film now look rather dated, but the way that he wears his relaxed-fitting flight jacket is anything but.
Mr Jefferson Hack
The British journalist co-founded the magazines Dazed & Confused, Another Magazine and Another Man, oversees the hip website Nowness, designs the Tod's No_Code range of shoes and is a fixture at the menswear collections in Milan, Paris and London. His presence at the shows is as reliable as his taste for woollen overcoats, understated tailoring, scarves, super-slim jeans and leather boots. It's a look that has impressed supermodels Mses Kate Moss and Anouck Lepère over the years, and which makes us wonder how long it's been since Mr Hack last enjoyed pudding.
Mr Richard Avedon
One of the foremost fashion photographers of the second half of the 20th century, Mr Avedon, a New Yorker, enjoyed prodigious success under the mentorship of legendary art director Mr Alexey Brodovitch. As an expert in the image business, Mr Avedon knew that simplicity in dress is often the best option, particularly on formal occasions.
Captain Jacques Cousteau
The world's most famous diver, who was a sort of marine-oriented, Gallic version of the BBC's Sir David Attenborough, combined elegant bearing with an enviable line in casual wear. We admire his habit of wearing a signature red beanie, but his button-down chambray shirts are genuinely inspirational.
Mr Alain Delon
The French-Swiss movie star may be known for wearing elegant tailored clothes, not least his incomparable trench coat and trilby outfit in the 1967 movie Le Samouraï, but in 1966's Lost Command he demonstrated how to look just as stylish dressed down in army fatigues. We're also impressed by the modern look of his cropped haircut.
Mr Porfirio Rubirosa
As a faithful servant of Dominican dictator Rafael Trujillo, and the unfaithful husband to five wives, two of who were enormously rich American heiresses, Mr Rubirosa was no role model. However, with a lifestyle that included playing polo, racing at Le Mans, and driving Ferraris, he has something to teach us about good living.
Mr Chet Baker
The US west coast jazz maestro, whose beautiful playing contrasted so strongly with his self-destructive lifestyle, wore simple clothes well. Back in 1961, playing his horn in Lucca, Italy, his long-sleeve polo shirt smartens up a pair of jeans. Fifty-two years later and this classic garment performs the exact same function.
Mr Errol Flynn
The Australian-born actor Mr Errol Flynn, whose 63-year-old outfit is only dated by the appearance of his pipe, was most often photographed in a jacket and tie. However, he looks far more at ease in this superb brown leather jacket, which reminds us that we've long promised ourselves a classic flight jacket.
Mr Arthur Miller
The New York playwright may not have enjoyed matinée-idol looks but, encouragingly, he still married Ms Marilyn Monroe. Here he sports a contemporary looking printed shirt, and a great pair of glasses, while maintaining a literary intensity. We like to think that it would still be a mixture potent enough to win the heart of a blonde bombshell.
Mr James Coburn
That this Hollywood tough guy had good taste is made clear by the cars he drove, which included a Ferrari Lusso and, famously, a 250 GT Spyder. It's hard to think of a better outfit in which to pilot a classic Italian sports car than a soft seersucker jacket, white shirt, slim tie and wrap-around shades.
Mr James Dean
The original teenage idol breathed style magic on most things he wore, from red bomber jackets to white T-shirts. Here Mr Dean lends some of his famous cool to a nautically inspired polo shirt, while demonstrating that the faff of blow-drying one's hair is repaid by the result.
Mr Phil Edwards
Mr Edwards, a legendary Californian surfer who'll be 75 this summer, surfed his first wave at nine, shaped his first surfboard at 13 and was surfing Hawaii's North Shore at 15. We're as impressed by the way his shorts balance style and athleticism as we are by the physical balance he demonstrates in this picture, taken at Virginia Beach in 1966.
Mr Edward Fox
The fact that the Duke of Windsor and The Jackal, two of the characters for which this British actor is best known, were beautifully dressed on screen is due in part to Mr Fox's interest in clothes. He remains impeccably turned out in Savile Row suits and handmade shoes, and only lets his sartorial guard down when he pulls on the worn corduroys in which he gardens.
Mr Neil "Bunny" Roger
Aside from his eye-catching Edwardian style this British dandy was also notable for being a WWII combat hero, and a dress designer. He ordered 15 suits a year from his Mayfair tailor, Watson, Fagerstrom & Hughes, and is said to have had four pairs of shoes made for every one. He rigorously maintained his slim figure (he had a 29" waist), the better to show off his unusual four-button suits.
Mr Tahar Rahim
This 31-year-old French actor, from Belfort on the country's eastern border, came to international attention in the 2009 film The Prophet, a tense prison drama directed by Mr Jacques Audiard. Although in the 2011 film The Eagle he wore an extraordinary camouflage suit made of animal skin we're more interested in Mr Rahim's ability to look both chic and relaxed, in an inimitably Gallic way.
Sir Mark Palmer
This British aristocrat now spends most of his time in rural Gloucestershire, but he was once a fixture on the London fashion scene. This was partly because he ran a model agency called English Boy, the USP of which was that the models looked like poets, but it was also down to the easy elegance with which he wore his velvet suits.
Mr David Beckham
The British football star has grown up in public, and part of that progression has been his developing sense of style. As he moves from the sports field to a more ambassadorial role his look is becoming increasingly formal, and he's frequently seen in slim tailoring that's entirely contemporary and entirely correct. His casual clothes are also becoming more stylish, and this combination is a masterclass in smart weekend wear.
Mr River Phoenix
The tragically early death of Mr Phoenix, who died aged 23 in October 1993, deprived us of both a great actor and a future style icon. In photographs he emerges as a man of grace and elegance. The image of him in a dinner jacket is a reminder of the spirit in which the tuxedo, the quintessence of male elegance, should be worn.
Mr Ludwig Mies van der Rohe
One of the preeminent modernist architects, Mr Mies van der Rohe was born in Germany, but left for Chicago in 1937. In his architecture he used the finest materials to create some of the 20th century's most beautiful buildings. He was no less exacting in his choice of clothes, as demonstrated by his exquisitely cut suits, at least some of which came from Viennese tailors Knize.
It's a testament to Lord Byron's 19th-century romantic poetry that, despite his extraordinary life story, he remains best known for his literary talents. Although described in 1812 by Lady Caroline Lamb as "mad, bad, and dangerous to know" we retain a guilty admiration for his romantic exploits, as well as for the claret shade of his velvet robes.
Sir Jocelyn Stevens
In between buying and reviving Queen, a British society magazine that catalogued the rise of swinging London, helping to finance the landmark pirate station Radio Caroline, running a couple of daily newspapers and later English Heritage, Sir Jocelyn Stevens found time to hone a fine taste in floral ties and relaxed tailoring - it's a look that wouldn't be out of place in an ad agency today.
Mr Sidney Poitier
In 1963 Mr Poitier became the first black man to win the Oscar for Best Actor, for his performance in Lilies of the Field. It came at a time when Mr Poitier was politically active in the Civil Rights movement, and photographs of the period show him on marches impeccably dressed in a slim black suit, white shirt and black tie. However, he was no less elegant off-duty, as this relaxed outfit demonstrates.
Mr Joseph Gordon-Levitt
This Californian actor first won attention in 3rd Rock from the Sun, and is now best known for his supporting role in Inception. However, it's Mr Joseph Gordon-Levitt's natural, unflashy style that sets him apart from the vast majority of young Hollywood actors, as demonstrated by this exemplary weekend look.
Mr Pablo Picasso
As one of the greatest artists of the 20th century, Mr Pablo Picasso knew a thing or two about making a visual impact. Born in Málaga in Spain, and buried in France's Aix-en-Provence, he embodied a now-vanished Bohemian Mediterranean lifestyle, never more so than when sporting a hoop-striped T-shirt.
Sir Michael Caine
One of the sharpest dressers in 1960s London, Sir Michael Caine eschewed (perhaps as a result of his humble background) the era's peacock style in favour of the kind of restrained but energetic tailoring that's entirely relevant today. Sir Michael relied on the late tailor Mr Douglas Hayward, but thankfully suits in cuts such as the one above are now more readily available.
Mr Paul Simonon
Somewhere between the rock'n'roll excesses of The Clash (he played bass guitar and frequently wore sleeveless denim jackets with nothing underneath them) and the sartorial excesses of his present pinstripe gangster look, Mr Paul Simonon hit a style sweet spot - here setting a fine example in a denim jacket.
MR Jean-Luc Godard
Not only was film director Mr Jean-Luc Godard able to create a vision of timeless cool when he made À Bout de Souffle (who wouldn't want to be Mr Jean-Paul Belmondo with Ms Jean Seberg at his side?) but he has exhibited a very modern style throughout his career. No man ever lost his hair with such nonchalance.
Mr Waris Ahluwalia
Born in India, Mr Waris Ahluwalia emigrated to America as a child. Some years later and his jewellery line has gained as much attention as his acting career, the highlights of the latter being roles in two films by Mr Wes Anderson. But it's the ease with which Mr Ahluwalia wears clothes that inspires our greatest admiration, as he demonstrates here with a casual deployment of a blue trench coat.
Mr LOUIS GARREL
The 28-year-old Mr Louis Garrel comes from a cinematic family of film-makers and actors. He achieved worldwide recognition with Mr Bernardo Bertolucci's 2004 film The Dreamers and has been providing a masterclass in louche Gallic style ever since, something reinforced by his relationship with Ms Carla Bruni's older sister Ms Valeria Bruni Tedeschi.
Mr RYAN GOSLING
The obvious reason to deny that Mr Ryan Gosling is currently the most stylish man in Hollywood is jealousy, brought on by the look women get in their eyes when his name is mentioned. From the tuxedos he wears on the catwalk to the scorpion bomber jacket from Drive and the navy shirt he wore at Cannes last year, Mr Gosling is currently setting the sartorial pace.
Mr TRUMAN CAPOTE
The American author, most famous for writing literary classic Breakfast at Tiffany's, was a dandy whose frivolous image belied the gravity of his dedication to his occupation. His personal style was exuberant, and chimes with the prints available this season from Burberry Prorsum, among other labels.
MR JEAN COCTEAU
The French artist, writer and intellectual was a man whose boldly creative spirit was always apparent, and entirely uncompromised by his fondness for suits and ties. The lean proportions of this soft-shouldered white suit wouldn't look out of place today. Although Mr Jean Cocteau once said, "Style is a simple way to say complicated things", we know looking this sharp isn't easy.
Mr Stefan Winkelmann
For an industry that is predicated on the idea of image, the auto world is surprisingly badly dressed. One of the very few exceptions is Mr Stefan Winkelmann, the German-born, Italian-bred CEO of Lamborghini. He is distinguished by his slim bespoke suits, spread-collar shirts, artfully dimpled Neapolitan ties and a penchant for brown suede shoes.
Mr JOE FRAZIER
The great boxer, who was narrowly defeated by Mr Muhammad Ali in the classic "Thrilla in Manila" bout in October 1975, enthusiastically embraced the fashions of the 1970s (including foot-wide lapels and platform shoes), but occasionally created a clothing ensemble every bit as devastating as the combinations he threw at his opponents in the ring.
Mr Clint Eastwood
When we're feeling lucky we aspire to look this good in a tweed jacket; Mr Clint Eastwood is simultaneously masculine and nonchalant in his semi-formal outfit. He demonstrates that tweed jackets work as outerwear, that there's no substitute for decent cloth and that an attitude is the ultimate accessory.
Mr Jean-Paul Belmondo
Mr Jean-Paul Belmondo was a leading light in French New Wave cinema and was acclaimed for his roles in Mr Jean-Luc Godard's Breathless (1960) and Mr Alain Resnais' 1974 film Stavisky. His style is anchored by two factors: his exemplary choice of clothes and the palpable sense that he doesn't give a damn. It's a potent combination.
Mr Robert Redford
Very cool in its own right, Mr Robert Redford's style really comes alive when he's in character, and never more so than when he was dressed by Mr Ralph Lauren for 1974's The Great Gatsby. Between the sumptuous suits and Mr Redford's aristocratic bearing, the film is a masterclass in how to dress up; the fully accessorised look is back in vogue this season.
Mr Gary Cooper
Born Mr Frank Cooper in the rugged state of Montana, this Hollywood star would have celebrated his 110th birthday this year. During his heyday, Mr Cooper's reputation as a snappy dresser was such that he was name checked in Mr Irving Berlin's 1930 song "Puttin' on the Ritz". His appeal lay not just in his enviable machismo, but in how he dressed appropriately for every occasion, from hunting with Mr Ernest Hemingway to lounging on a yacht.
Mr Clark Gable
The star of Gone With the Wind is remembered as an impeccably groomed smoothie, which conceals the fact that his studio, MGM, initially promoted his unpolished masculinity. Despite these origins few men have ever worn clothes as well as Mr Gable, whose appearance in his publicity photographs probably explains why the co-stars he enjoyed romantic success with included Ms Grace Kelly and Ms Joan Crawford.
Mr Ryan O'Neal
The star of the 1970 film Love Story, in which he appeared alongside the beautiful Ms Ali MacGraw, is a style icon whose look was particularly on-trend last season. The traditional collegiate clothes he wore in the film seemed to strongly influence the collections, which picked up on his character's taste for corduroy, tweed, sheepskin and chunky Aran sweaters.
Mr Gore Vidal
One of America's grand old men of letters, Mr Vidal made his mark in 1948 with his third book The City and the Pillar. A fine example of his ability to martial the English language was when, having been dropped by a punch from a famously pugnacious author, he quipped from the floor, "Words fail Norman Mailer yet again". It's somehow appropriate that this freethinker favours a relaxed soft-shouldered jacket.
Mr David Bowie
Sartorial chameleon Mr David Bowie could easily be five different style icons, but to our eyes his best-dressed era was the late 1970s and early 1980s, when he mined a seam of fashionable tailoring that demonstrates that it's possible to wear the traditional elements of menswear but make them entirely your own. Although few other men could carry off this sage-green suit, many could take a leaf out of his book with regards to the bow tie and plaid shirt combination.
The Duke of Windsor
Although the list of his other virtues is short the duke is widely considered to be the best-dressed man of the 20th century and his clothes were exemplary in many ways. He was best known for the suits that were superbly tailored for him, primarily by Mr Frederick Scholte on Savile Row.
Mr Gregory Peck
The Californian actor Mr Gregory Peck made his first film, Days of Glory, in 1944, and by 1949 he'd been Oscar-nominated for four different movies. Among his famous roles he played Atticus Finch in the film version of To Kill a Mockingbird, in which he set the bar high for men aspiring to wear off-white, three-piece suits, and Joe Bradley in Roman Holiday, in which he was sufficiently stylish to capture the heart of Ms Audrey Hepburn.
Mr Tom Waits
Mr Tom Waits' voice has been described by rock critic Mr Daniel Durchholz as "like it was soaked in Bourbon, left hanging in the smokehouse for a few months, and then taken outside and run over with a car". And the singer's style is correspondingly rugged, whether he's dressed in a suit or, as here, in classic workwear.
Mr Rupert Brooke
The floppy haired English poet behind The Soldier ("If I should die, think only this of me/ That there's some corner of a foreign field that is forever England") was a very modern character despite being born in the 19th century. In 1915 he died of a septic mosquito bite on his way to Gallipoli, but he found time before then to embrace a romantic vision of elegance that has a very contemporary appeal.
Mr Steve McQueen
Mr Steve McQueen is a style icon regular. And, to avoid being predictable, we really did try to leave him out of this one. But it just felt wrong. Come on, the guy starred in The Great Escape, Bullitt and The Thomas Crown Affair, loved racing motorbikes, married Ms Ali MacGraw, and wore chinos and Persols like no one else.
His Imperial Majesty Haile Selassie
His Imperial Majesty Haile Selassie was the Emperor of Ethiopia from 1930 to 1974. In fact, his full title was: His Imperial Majesty Haile Selassie I, King of Kings, Lord of Lords, Conquering Lion of the Tribe of Judah, and Elect of God. He was also, at the time of his reign, the most bemedalled ruler in the world. Befitting for someone who could trace his ancestry back to King Solomon and the Queen of Sheba, Selassie could certainly rock up a regal look or two.
Mr Gianni Agnelli
Mr Giovanni "Gianni" Agnelli was an Italian industrialist, president of Fiat and, according to many at the time, the true king of Italy. While he ruled over the Italian economy and European high society during the 1960s, 1970s and 1980s, he was admired as much for his dress sense as he was for his business acumen. He mastered the art of sprezzatura - making the difficult look easy. His style trademarks included wearing a watch over his shirt sleeve (saves time) and leaving his tie slightly askew, or hanging over his sweater. It may have looked accidental, but Mr Agnelli wasn't a man to leave anything to chance.
Mr Cristóbal Balenciaga
Mr Cristóbal Balenciaga was the Spanish designer who, in 1937, founded his world-famous eponymous fashion house in Paris. He was responsible for dressing some of the most powerful women of his generation (the Queen of Spain, the Queen of Belgium, the Duchess of Windsor and Princess Grace of Monaco) and regarded as "the master" by many, including Mr Christian Dior and Ms Coco Chanel. A devotee to monochrome tailoring, Mr Balenciaga became synonymous with the sharp double-breasted suit.
Sir Mick Jagger
Admittedly, it shouldn't be too hard for a skinny, long-haired rock star to figure out how to work a look. Especially in the 1960s. But this Rolling Stone, along with drummer Mr Charlie Watts, nailed it immediately. And Sir Mick Jagger has continued to do so ever since. Admirably, he has happily shown that colour, pattern and a good fit can work for even the most red-blooded of us.
Mr Johnny Depp
Mr Johnny Depp exhibits a distinctive and eclectic personal style that's not easy to find among his generation of actors. His love of worn-in clothing, oversized dress shirts and heavy accessorising gives him a look that's part grunge, part Bohemian and part eccentric millionaire. Hats off.
Mr Marcello Mastroianni
Mr Marcello Mastroianni, the suave Italian actor, became synonymous with style after his role as the playboy journalist in Mr Federico Fellini's La Dolce Vita, alongside Ms Anita Ekberg and Ms Anouk Aimée. There was substance to the man, too: he is one of only three actors in history to win Best Actor twice at Cannes. And he fathered a child with Ms Catherine Deneuve. Respect.
Colin Tennant, Third Baron Glenconner, was famous for having fun. And who can criticise a guy for that? He bought the West Indian island of Mustique - most of us make do with just booking a hotel - and transformed it into a multimillionaire's playground in the late 1960s. A gregarious host, and close friend of Princess Margaret, Lord Glenconner dressed like the quintessential tropical patriarch, peppering his wardrobe with bright colours, tunics and wide-brimmed hats. And it somehow worked.
Mr Bob Dylan
Mr Bob Dylan has undergone many musical and aesthetic changes during his 50-year career. But there is no denying his genius and the way he can carry a tune and, more impressively, a lyric. There aren't many songwriters whose words have become anthems for civil rights and anti-war movements. One of the most influential cultural figures of the 20th century, we're going to be very superficial and just point out how good a man can look when he finds the right black leather jacket.
Mr Lapo Elkann
Mr Lapo Elkann, the manager of brand promotion at Fiat - a company once led by his highly stylish grandfather, Mr Gianni Agnelli - is by no means your typical Italian scion. His personal life has been as playful as his dress sense. A regular at all the best parties - as well as on Vanity Fair's annual Best-Dressed List - we love the way he takes all the menswear rules and throws them artfully in the air.
Mr Jean-Michel Basquiat
Mr Jean-Michel Basquiat was a graffiti artist on the 1980s New York art scene, legendary for wearing high-priced designer suits to paint in. In his short 27-year life he modelled for Comme des Garçons, starred in a Blondie music video, dated Madonna and collaborated with Mr Andy Warhol.
Mr Terence Stamp
Mr Terence Stamp is one of the best-dressed men in London. He was an early client of legendary Mayfair tailor Mr Douglas Hayward, lived at Albany, the prestigious bachelor apartments in Piccadilly (never call it The Albany), and starred in genius movies such as Billy Budd, Far From The Madding Crowd and The Limey. We won't dwell on his role as General Zod in the original Superman movies, but on the fact that the man is a legend who, along with his former girlfriends, Ms Julie Christie, Ms Brigitte Bardot and Ms Jean Shrimpton, embodied all that was good about the swinging 1960s.