Best-dressed lists have a tendency of being predictable affairs.. The same chisel-jawed models and Hollywood actors are proffered up as arbiters of good taste, all because they wore what their personal stylists picked out for them on the way to the latest red carpet.
As much as we love them, this list is a little different. This is our homage to the men who are more than just handsome clothes horses – though handsome many of them indeed are (never hurts, does it?). Men who dress to their own beat. Men who are the picture of elegance, insouciance and – occasionally – courage, all embodying Orson Welles assertion that “style is knowing who you are, what you want to say, and not giving a damn.”
From designers to artists, entrepreneurs to business leaders, to – yes – one footballer (no, not that one), this is a list of the real best-dressed men in the world right now – and what we can all learn from them.
Edited by Teo van den Broeke. Words by Teo van den Broeke, Sam Parker, Charlie Teasdale and Emie James-Crook.
1Alessandro Squarzi, entrepreneur
The Italian fashion entrepreneur and street style icon is the real star of the Pitti Imaginaire ‘Peacocks’. Where others preen and posture in their fussy, over-tailored outfits on the benches outside the Florence trade show, Squarzi is the master of understated Italian cool, but with a more American leaning (see his impressive arsenal of field jackets and military shirts). If you’ve ever wondered how to wear white trousers with ease, see Squarzi, and emulate.
2Alex Turner, musician
The Arctic Monkeys frontman is but a shadow (puppets; last of) of his former self, a million miles from the indie rock scruff that emerged back in 2006. As the command of his on-stage persona has developed, so too has his style, and it’s admirable. Few men can pull off the full greaser look, and even fewer can maintain respect when whipping out a comb and seeing that all upstairs is in order, but he does it.
3 Alexandre Mattuisi, fashion designer
Despite his success with almost-eponymous brand AMI, Mattuissi is clearly a man that doesn’t take clothes too seriously, or at least not those he wears on his own back. Mirroring the aesthetic of AMI, we could describe his wardrobe as ‘prep 2.0’. That is to say; oxford shirts, cardigans, simple knitwear, soft-shouldered overcoats, occasional loud trainers and inevitable beanie hats. As if a Silicon Valley tech kid took up residence in Montmartre for a year or two.
4Alasdhair Willis, brand director
As the former publisher of Wallpaper magazine, current creative director of Hunter and long-time husband of fashion designer Stella McCartney, it’s hardly surprising that Alasdhair Willis has, over the years, developed an enviable signature style. His mane of salt and pepper hair and impressive beard aside, Willis’s wardrobe of beautifully cut suits (the man knows how to go double breasted), slick roll necks and chic field jackets is an enviable one.
Perhaps it’s the flowing locks, perhaps it’s annoyingly good hipster beard, perhaps it’s the ability to pinpoint a pass with the precision of a Swiss watchmaker – whatever it is, it’s hard to think of a more stylish footballer alive today than Milan and Juventus legend Andrea Pirlo. Like all members of his tribe the 37-year-old is often spotted in casual sportswear – something he manages to look far better than it should – but when he’s not on duty, Pirlo’s Italian heritage shows with impeccably tailored suits, generally worn with lightly disheveled shirts and casual boat shoes.
6Ben Cobb, editor
Hailed by The New York Times as ‘wonderfully sleazy’, Ben Cobb – the editor of biannual style title Another Man – is the embodiment of sexed up Seventies style. With a wardrobe chockablock full with wide lapel double-breasted jackets, jewel-toned flared trousers and open necked silk shirts with slick spread collars, Cobb has a look all his own – and it’s not one you see very often. “Louche is the word most often used by people to describe my style.” Says Cobb. “I suppose it is. My look is heavily rooted in the 1970s – unbuttoned shirts, jewelry, tailoring, flared trousers and always with a well-heeled boot. For me, that decade is still the chicest moment in masculine style.”
From busking barefoot on the streets of Paris to brightening up the Burberry catwalk with his soulful voice, Mercury prize-winning musician, artist and poet Benjamin Clementine is a true Renaissance man with a unique style all his own. Having once said he would prefer to perform totally naked, Clementine often swaps shirts for a bare chest under a suit. In winter Clementine cuts a fine silhouette in long structured coats teamed with dark roll necks. The finished look treads an elegant line between sharpness and ease.
8Bill Nighy, actor
Once, talking to Mr. Porter, Bill Nighy described his perfect navy suit – the outfit that is very much his adopted uniform. “Very simple, lightweight, two-piece, two-button,” he said. “And it’d be single vent, two buttons on the sleeve, not a particularly wide lapel, not particularly styled, not a waisted jacket. It would have a single pleat, relatively narrow trousers, which you’d wear reasonably short, so they hit the shoe correctly”. Thus the actor summed up perfectly why he is Britain’s best-dressed thespian: simple but precise, understated but elegant, and always, always fit for the occasion.
9Brunello Cucinelli, fashion designer
Founded 37 years ago, Brunello Cucinelli’s eponymous company – which is based in Solemeo, a hilltop village in Umbria– produces some of the most beautiful menswear known to, well, man. Advocating comfort, softness and an easy approach to the Italian concept of sprezzatura, Cucinelli is the embodiment of his brand. Most often found wearing a navy cashmere blazer, a swiftly knotted tie with a button down Oxford and a pair of perfectly tapered charcoal trousers (which probably cost the same as a second hand car).
A man with that most enviable of sartorial abilities – to make any outfit, not matter how formal or flamboyant, look raffish and unaffected – the Roxy Music front man embodies Hardy Amies’ maxim that a man should “look as if he has bought his clothes with intelligence, put them on with care and then forgotten all about them”. Whether it’s a battered approach to black tie, somehow making tennis whites seem rock and roll or turning up at Buckingham Palace in a tailcoat and matching black and grey striped trews, he’s a man to whom only one fashion rule seems to apply: be the best-dressed in any room, without seeming to try.
11Charlie Casely-Hayford, fashion designer
In a recent panel discussion at the Esquire Townhouse, Casely-Hayford explained the pleasure he takes in the ease of dressing each morning. “I like the idea of having a uniform,” said the designer, “the permanence of knowing I can wear the same thing every day. I can wake up in the morning and know my wardrobe is very simple. I have 100 pairs of red socks; six pairs of military boots; black t-shirts and navy tailoring. That’s it, really.” Moreover, we can all learn something from Charlie’s stoic standpoint: when you find something that works for you, stick with it.
With his landmark 2012 show ‘A Bigger Picture’ Hockney took the quaint British countryside and invigorated it with vivid colour and unusual perspectives. The 79-year-old approaches his wardrobe with similar verve. Bright accessories and pastel shades make his fondness for preppy sportswear and – in later years – soft tailoring look somehow new. Then of course there are his signatures – the circular specs, the sweep of blonde hair (well, white now), the ever-present cigarette – that help make Hockney not just our greatest living painter, but our best-dressed one too.
13David Adjaye, architect
If you’re giving man a load of money to design you a building, you’d want him to dress like David Adjaye. Simple, unstructured tailoring, soft shirts and crew necks, and when the time calls, a few well-chosen layers. He said of his work that “the business of being an architect is not about perfecting one’s style”, however it would seem he has done just that with his wardrobe.
14Eugene Tong, stylist
Few stylists have as good a handle on the mix of proportion, fit and palette that goes into making men look good. A street style stalwart, Tong fuses tailoring, essentials and street wear – if you don’t believe in the simple power of a white T-shirt or that running shoes can be worn with suit separates, prepare to be convinced – and demonstrates perfectly that ‘men’s style’ is about more than just three-piece tailoring. “Dress for your body type, don’t jump on every trend and view fashion as an investment.” Some sage advice there.
Look around Henderson’s restaurant St John in Smithfield, London and you’ll see the place perfectly mirrors the founder’s sense of (life)style. The space is sparse, but comfortable and moreover, logical – a place you go to eat good, simple food, not marvel at art or gawp and the carefully curated gladioli. This sense of function can be seen in Henderson’s wardrobe. You’ll rarely see him out of a royal blue work shirt and a pair of sturdy brogues – with an oxford, sleeves rolled to the bicep, all so he can better wrestle a pig of its innards, one might imagine – and those little round spectacles, which tie it all together.
16G Bruce Boyer, writer
A former fashion editor of Esquire, septuagenarian Boyer has previously spoken about his willing to sacrifice comfort in the cause of style, which is perhaps why you never see him out of a shirt, tie and bench made shoes. His understanding of colour and texture, however, is second to none, and we’d go so far as to say that he’d easily give Ralph Lauren a run for his all-American (with classic English lilt) money.
17Gordon Richardson, fashion designer
“I tend to wear simple pieces in a subdued palette of grey, navy and black that focus on subtle details inherent in the cut, proportion and fabric.” Says creative director of Topman, Gordon Richardson. Always elegant with a functional edge, Richardson demonstrates – with aplomb – how to dress well as an older man. “Trends are something I have to subtly navigate around dropping in and out where applicable.” He says. “I style and mix these pieces depending on mood and circumstance throwing in a neckerchief or skater sweat. I favour these in white as they are good freshening up pieces that compliment my grey hair.”
One of the most versatile men in front of the camera is also one of the most straightforward off it, which is to say Gary Oldman has found a winning look and stuck with it. His hair is just the right side of curtains, his beard the right side of thesp-goatee, and his chunky glasses the right side of haughty graphic designer. Add the above to a penchant for dark suits and impeccable tuxedos (both most likely by Prada, for whom Oldman has recently modeled), and you’ve got a recipe for the most simplistically stylish actor of his generation.
19Giorgio Armani, fashion designer
Last year Giorgio Armani celebrated the 40th anniversary of his eponymous brand with a suitably decadent party in Milan. While guests such as Leonardo di Caprio and Robert de Niro dressed up for the occasion in Armani’s classically sharp evening wear, Mr Armani kept it simple in his uniform of deconstructed single-breasted navy blue jacket and slightly contrasting wide legged pants. It’s this unerring dedication to a unifying aesthetic that has seen Armani become arguably the most successful Italian fashion designer in history. Famous for introducing the deconstructed suit to the world, by way of Richard Gere in American Gigolo, Mr Armani’s personal style is understated, simple and effortlessly chic – confined as it is to a palette of dark blue and grey with a consistently soft silhouette. Belissimo.
Since 2001, Columbian designer Haider Ackerman has been producing androgynous menswear with a multicultural flavour for his eponymous label. As of Autumn Winter ’17, however, Ackerman will be ensconced in a new role as creative director of key LVMH pillar, Berluti. As much as we’re taken with the designer’s professional output, it’s Ackermann’s personal style that has most caught our attention. A fan of oversized scarves, perfectly cut silk trousers, drapey deconstructed tailoring and clever colour combinations; Ackermann’s approach to dressing is stealthily sexy. “Clothes should never be decoration”, says the designer. “When someone feels at piece with their clothes, they feel more seductive, more desirable, more sensual, more everything.”
21Jarvis Cocker, musician
Most of us cringe remembering what we wore as a 20-something in the 90s. Not so the great survivor of Britpop Jarvis Cocker, who does now exactly what he did then by eschewing trends completely in favour of a look that is entirely his own. Although elements of Cocker’s style – the drain pipe trousers, the horn-rimmed glasses, the second-hand suits – have since been appropriated by a certain strain of wannabe-bohemian hipsters, with him it’s the real deal, somehow convincing us all that the best clothes aren’t to be found on Bond Street or Lamb’s Conduit but tucked away in your local Oxfam.
Hack has been a fixture of the ‘scene’ for over 25 years, so after all the deadlines, parties and fashion weeks (we can only imagine), you’d expect him to show signs of wear, but he doesn’t. As youthful as ever, he has managed to defy the odds and stay cool. Against further odds he still looks good in skinny jeans, leather jackets and printed shirts, and few of fashion’s high society can layer up a blazer with such aplomb.
23Jeremy King, restaurateur
As one half of the duo behind some of London’s most stylish restaurants (The Wolseley, The Delauney etc.), it goes without saying that King is rarely seen out of a perfectly cut suit and tie. The latter is often boldly coloured or printed, which we normally wouldn’t be so keen on, but it tends to work. Perhaps they’re offset by the ever-present peak lapels, or softened by the ubiquitous double-breasted cut of his jackets. Either way, he clearly knows what he likes, and you’ve got to respect that.
24Luciano Barbera, tailor
“I do not believe in stiff shoulder pads. That is vanity, not style. And do not wear your jacket too tight. If it’s too tight, you will look like a matador.” Says tailor and street style star Luciano Barbera. The son of a fabric Magnate, Barbera has been making his own clothes since 1971. Focused on fabric and cut, Barbera is a also master of unexpected cloth combinations – think grey window pane check cashmere with jumbo caramel cord – his style philosophy is as follows: “it is not enough to have beautiful clothes. Lots of people have beautiful clothes. In fact some people have too many. What is important is what you do with them.”
Spanish Shoe designer Manolo Blahnik has been making slippers and stilettos for the well-heeled men and women of the world for the past forty years. Famous for his flamboyant designs (your girlfriend probably has a hankering for his be-jeweled Hangisi pumps), Blahnik’s penchant for peackockery extends from his atelier to his wardrobe. A fan of pastel suits from Savile Row tailor Anderson & Sheppard, bright bow ties from Parisian shirt maker Charvet and foppish loafers from his own collection, Blahnik’s style is nothing if not specific. “I like men with a touch of femininity” he told Esquire last year. “I like things that aren’t too serious.”
26Oliver Spencer, fashion designer
Self-taught tailor and shopkeeper Oliver Spencer’s runway collections are as relaxed and modern as his approach to his own wardrobe. Since founding his eponymous brand in 2002, Spencer has maintained a ‘casual needn’t mean careless’ philosophy. Pairing muted roll necks and loosely fitted layers with unstructured tailoring. He explained his understated approach to his clothes at the Esquire Townhouse last year, when he said: “In my opinion, to be seen and not heard is the best thing.”
“Style is something assembled over time. As we pass through life we collect the building blocks of our style, from people, from books, from films, from everywhere. Our style is built not just of clothes but of manners and mannerisms.” Says Patrick Grant, owner of Savile Row brands E Tautz and Norton & Sons, general man about town, and handsome fan of wide legged trousers and billowing work shirts. “Once we’ve built our style we tend to like to stick to it, which is why I like brands that do one thing, do it consistently, and do it best.”
28Prince Michael of Kent, royal
There had to be one royal in the mix – they do well out of the multitude of Savile Row warrants, after all – but it isn’t Charles, it isn’t William and sadly, it isn’t little George. The ruler in the style stakes is Prince Michael of Kent, cousin of the queen and a deft hand with a beard trimmer. For a man that typifies quintessential British style (tweeds, country brogues, navy melton wool and the like), he has an Italian inspired way of dressing that no other high-born aesthete can match: wide peak lapels, contrast collar shirts and fat, skewiff knot on every tie. Molto bene.
29Ralph Lauren, fashion designer
“Style is very personal. It has nothing to do with fashion. Fashion is over quickly. Style is forever,” Ralph Lauren once said. And while fashion may be his business – he remains at the head of one of the most recognisable and revered labels in the world – a personal sense of style is very much part of why the 77-year-old still inspires such respect. No one makes the denim and checked shirts of his American heritage look better – certainly not when paired with a double-breasted jacket and worn on a ranch.
Potentially the most photographed man on the menswear circuit, stylist Robert Rabensteiner has become as well known for the world-class outfits he wears as for the work he produces for the pages of L’Uomo Vogue, Purple Fashion and The Wall Street Journal. As partial to a sharply cut suit jacket with a popped collar as he is to a bow tie and teddy bear coat combo, Rabensteiner is a true original, and helpfully handsome with it.
31Stefano Pilati, fashion designer
The former creative director of Yves Saint Laurent (as it was then known) and Ermenegildo Zegna, Stefano Pilati is one of menswear’s great contemporary visionaries. Famous for producing richly textured collections with a focus on impeccable cut, Pilati himself is a shop window for his work – he’s mentioned in several interviews that he only designs clothes for himself. A master of proportion, Pilati’s wardrobe is a slouchy symphony of wide-cut pleated trousers, smart penny loafers and perfectly cut double-breasted jackets. “I have a big and very colourful wardrobe.” Pilati told the Wall Street Journal in 2012. “From this I can put together many looks in different ways.”
A dandy in his younger days, the British actor’s style has mellowed over the years, although the odd jaunty paisley neckerchief remains. Today, he is an exponent of the simple virtues of the suit (more often than not, three-piece), and those virtues go beyond aesthetics, as he wrote in the A/W’13 issue of Esquire‘s Big Black Book. “You’ve got to have a suit that you feel good in,” said Stamp, “and you might get lucky, so you’ve always got to wear a suit that you feel good taking off. You must be able to get out of a suit if you get into mischief.”
33Tom Ford, fashion designer and film maker
The Lone Star State’s most stylish son was a natural addition to this list. Like many of his more stylish fashion designer contemporaries, Tom Ford generally sticks to a uniform, which in his case consists of a slim cut single breasted black suit, a white spread collar shirt and a slightly wider than fashionable tie (and let’s not forget those degrade aviators). The thing with Ford is that whatever he wears he always looks impeccable, much like the work he produces – be it a film or a fashion collection. “I probably do have an obsessive personality.” Says Ford. “But striving for perfection has served me well.”
50 year-old New York Artist Tom Sachs – who is best known for producing work challenges the boundaries between fashion and art (he made a Prada-branded toilet and an Hermes-branded happy meal in 1997) – wears the same outfit day in, day out. Consisting of a white button down shirt from J Crew (complete with a pocket full of colourful pens), a plastic G-Shock watch, a pair of aviator style spectacles and a three-pocket chore coat, Sachs has embraced the power of the uniform to prodigious effect.
35Tremaine Emory, brand consultant
Part club promoter, part fashion consultant and part curator, hulking New Yorker Tremaine Emory cut his teeth working for Marc Jacobs in London. One half of the duo responsible for nomadic club night No Vacancy Inn – which regularly hosts achingly cool parties on both sides of the Atlantic – Emory also spends much of his time working with Kanye West on his clothing line. Emory’s personal style is a heady mix of 80s New York hip-hop influences, high fashion and modern street wear. As likely to be sporting the latest runway creations from Prada and Gucci as he is wearing neo-street pieces from Off White and Hood By Air, Emory’s aesthetic fizzes with irreverent creativity ” My style is a conglomeration of all the books, movies, music and art I’m into.” Says Emory. “It’s also very influenced by growing up in New York (Jamaica, Queens) and spending loads of summers in Harlem, Georgia.”
Creative director of cult street label Off-White, close collaborator of Kanye West and erstwhile furniture designer, Virgil Abloh is one of the coolest men in the world right now. Combining a street wear aesthetic with a more polished sartorial sensibility (think skater hoodies teamed with slim white jeans and beautifully cut cashmere overcoats), there’s an intriguing incongruity to the way Abloh dresses, and it’s a look he owns.
37Vladimir Restoin Roitfeld, art dealer
The son of womenswear doyen Carine Roitfeld, Vladimir Restoin Roitfeld was always destined to dress well, but the art dealer has made his look his own by channeling a gothic vibe. He likes structure in his shoulders and a big collar, which would look silly on a shorter, stockier man, but it lends VRR a slightly vampyric edge. Impossibly tall, annoyingly thin – his very body was created for the sole purpose of wearing Saint Laurent suits.
38Warris Ahluwalia, actor and designer
American auteur Ahluwalia has only appeared in a few films, but stylistically, he hasn’t gone far wrong, seeing as they’re nearly all directed by Wes Anderson. When he isn’t acting, he’s designing under the moniker of House of Warris, a brand that has collaborated with the likes of APC, Pringle of Scotland, Colette and the Kooples. His style is simple but smart – lots of slim tailoring, and shirts open to the chest, but that’s what you would do if you were as lithe, tall and bearded as he, right?
Friend of Esquire and elusive man about town, Gilchrist is one of the most sought after stylists in modern publishing. A man with natural cool, you’ll occasionally see him on a fold up bike whizzing through traffic, cigarette in hand and scarf blowing in the wind. In terms of actual clothing, he’s not often out of an impeccably cut double-breasted jacket, and has taken up the mantle of Number One Safari Jacket Wearer in Yves Saint Laurent’s absence. He once told us that he machine washes the fabric of his chino suits before having them made to ensure that he can wash them with ease after every wear. Now if that’s not dedication to the cause, we don’t know what is.
40Posthumous mention | AA Gill, writer
When we first began compiling this list last year, Esquire‘s then-columnist AA Gill was one of the first names we wrote down. Sadly, Adrian died in December 2016 before we had the chance to publish.
In a profession increasingly run by 20-somethings in hoodies, Gill was perhaps the last of a great breed: a journalist with a true sense of individual style, both on the page and off. Gill’s prose was playful, provocative and occasionally flamboyant and his dress sense was the same. Classic English tailoring, a fondness for bow ties and the occasional peacocking cravat were all part of his arsenal. On dressing well, then, we’ll give him the final word:
“There are only two words you need to remember. They are ‘nonchalance’ and ‘elan’. The problem is they are usually mutally exclusive, but you need to dress with elan and wear your clothes with nonchalance. The worst-dressed man in any room is the one who won’t order spaghetti because he’s got a Hermès tie on.”