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The 20 Greatest (Fictional) Style Icons Of All Time

The 20 Greatest (Fictional) Style Icons Of All Time

The 20 Greatest (Fictional) Style Icons Of All Time

Real-life heroes are all well and good, but make-believe ones are better. Our crack team of 13 experts select their fantasy fashion inspirations...

Dennis the Menace

Chosen by Henry Holland

“The original rule-breaker with great knitwear. He looks like he arrived on the pages of The Beano direct from walking for a Saint Laurent collection.” That’s how designer Henry Holland describes comics’ naughtiest kid. Dennis keeps his signature look to just two colours and is so style-focused that he’s matched his hair with his pet. We think Karl Lagerfeld may have snatched a few ideas from Dennis.

James Bond

Chosen by Anthony Horowitz

“Bond applied perfect taste to everything from his clothes and cars, to his drinks, toiletries and cigarettes and who, in From Russia With Love, knew that Grant Donovan was up to no good from the way he tied his tie.” Bond has a classic style, yet each incarnation has his own modern touches.

Doctor Who (Matt Smith)

Chosen by Jonathan Pile

“Only a truly stylish man can make a derided item of clothing covetable. Daytime bow ties were the preserve of history professors and Porky Pig. The Doctor made them work by wearing them in unusual fabrics against clashing patterns.”

Clark Kent

Chosen by Adrian Clark

“The red underpants over blue tights get-up is iconic, but it’s a lot of look. Off-duty, Superman has classic office style: sober suits, neat shirt and tie, neutral Mac and perfect square-framed glasses. His out-of-office outfit may get him noticed, but his day job clothes can take him anywhere.” 

Thin White Duke (Bowie)

Chosen by Oliver Spencer

“Bowie plays with shapes, so while the waistcoat kept the top-half silhouette trim, the trousers might be oversized and the collars enormous. It’s elegant but not remotely dull, kind of androgynous but worn with a masculine confidence.“

Ferris Bueller

Chosen by Kit Neale

Print-loving designer Kit Neale describes his idol as “smart, handsome, witty and with a ridiculously brilliant wardrobe”. In keeping with his character, nothing about Bueller’s clothes is easy. He wears patterns that have no business with each other, and lip-syncs while wearing a geometric vest that your mum would be embarrassed to own, yet on him it is cool. He shows that dressing like a rebel doesn’t have to mean leather biker and a snarl.

Detective James Crockett (Miami Vice)

Chosen by Henry Holland

Even if you didn’t watch the show, your holiday wardrobe probably steals a few ideas from Eighties Don Johnson. “Pastel suits with T-shirts, espadrilles, rolled-up sleeves,” says Henry Holland. “The influence Mr Johnson had on men’s fashion is still clear to see.” 

Tyler Durden

Chosen by Katie Eary

“Tyler loves an all-over print. His Nineties belly tops are super sexy – I don’t know any guy that didn’t want to dress like him,” says Katie Eary of Brad Pitt’s defining role. You need Pitt’s swagger to carry off vintage porn-print T-shirts with cherry-coloured biker jackets, or shirts with huge Seventies collars teamed with rose-tinted shades. But you could steal elements of it. And we did.


Chosen by Tommy Hilfiger

“My brothers and I loved Tintin comics when we were young,” says Tommy Hilfiger. “I will never forget his signature look: chinos, a sweater, trench coat and loafers.” Tintin’s trademark clothing is about practicality. He’s dressing for adventure but never lets his standards slip. That’s an outlook we’d all do well to copy.

Tony Montana (Scarface)

Chosen by Astrid Andersen

“Everything about Pacino’s look says he’s in charge. His suits cost more than most cars, but he wears them lightly, with buttons undone and sleeves rolled up. He’s never sloppy, though; notice that whenever there’s a suit jacket on, there’s a pocket square at his breast – even when he’s covered in blood and coke.”

Marty McFly (Back to the Future)

Chosen by Lou Dalton

The time-hopping teenager looks thrown together, but examine his outfit more closely. He’s toned his T-shirt with his puffa (worn despite the sunny weather), and he’s mixing patterns and denim washes. As Lou Dalton sums it up, “He could give any kid in Shoreditch a run for their money and win hands down.”

Han Solo

Chosen by James Long

Nothing about Solo’s outfit sounds good: a collared T-shirt slashed down to the sternum; a pocketed waistcoat; knee-high boots. You’d get laughed out of even the edgiest parts of east London if you turned up in that combo. Yet, somehow, when it’s all worn together and teamed with some Harrison Ford insouciance, it manages to look practical and elegant. There’s a reason why every Star Wars fan wants to cosplay as Han (unless they’re cross-dressing as Leia in a bikini, but that’s a whole other conversation).

Dickie Greenleaf (The Talented Mr Ripley)

Chosen by Gordon Richardson at Topman

As played by Jude Law, Dickie spends his days on beaches and nights in salubrious bars. His look matches. By day; bold swim shorts and barely buttoned shirts; by night he’s suited, but in laidback fabrics. It’s a style for the genetically and financially blessed.

Sherlock Holmes

Chosen by Tommy Hilfiger

“I love to reinterpret heritage classic in a new way, and often look to English style for inspiration,” says Tommy Hilfiger. “Sherlock Holmes epitomises traditional British fashion.” The Cumberbatch version made men lust after the double-breasted Belstaff coat he wears – it had to be reissued, then sold out again.

Fantastic Mr Fox

Chosen by Lou Dalton

“A feral fellow with a strong will to survive; sensitive and charming” is how Lou Dalton describes the vulpine hero. Yes, he’s a puppet, but – with a wardrobe modelled on the film’s spiffy director, Wes Anderson, with double-breasted corduroy blazers and velour polos – he’s more stylish than most human stars.

Renton (Trainspotting)

Chosen by James Long

For one, Renton, as played by Ewan McGregor, did skinny jeans way before they became ubiquitous, with T-shirts one size too small, unearthed from a charity shop. His look was part mod and part Sid Vicious. Don’t choose his life. Choose his wardrobe.

Maverick (Top Gun)

Chosen by Adrian Clark

“It’s all about those aviator sunglasses and the flight jacket. Just about every man of a certain age has tried out that look, hoping that these things – added to a white T-shirt and a pair of Levi’s – will make them worthy of the name Maverick. And as long as you dial back the badges, it’s a style that works for almost anyone.”

John Steed (The Avengers)

Chosen by Sir Paul Smith

Fighting criminals does not mean one has to wear tights. Unlike the modern Avengers, the hero of the Sixties show dressed like a gentleman, down to his bowler hat. The suits are cut close to the body with some quietly jaunty patterns. From a distance he looks conservative, but up close there’s a touch of rebellion.

Julian Kaye (American Gigolo)

Chosen by Gordon Richardson at Topman

For decades there had been a tradition of fashion designers creating bespoke wardrobes for women in films, but American Gigolo was one of the first films to make the man the style focus. The suits Armani put on Richard Gere, as a louche male escort, established the designer in the US and created a suave look that still crops up on catwalks.

Tony Manero (Saturday Night Fever)

Chosen by Adrian Clark

“John Travolta’s character took dressing for the weekend to its apex. It’s unashamed peacocking. Terrible things have been done by people trying to imitate that white suit, chosen by costume designer Patrizia von Brandenstein to show up the disco lights, but look at the original. Bold? Yes. Cool? Absolutely.”