45 Famous Tomboy Icons In Hollywood

45 Famous Tomboy Icons In Hollywood

Actually, boy-meets-girl dressing is big news – so take your style inspiration from the tomboy. There are famous tomboy icons in Hollywood

Ruby Rose keeps it casual in LA. The Orange is the New Black star wowed us with her perfect tomboy style, and gave us perfect androgynous summer inspo.

Kristen Stewart is fast becoming the new Queen of androgyny, subjecting her sharp, delicate features to cigarette trousers and oversized suit jackets. She can even take it one step further, scrape her hair back and wear clumpy loafers – her beauty only fuels the irony.

Not one to be outdone by her man, Angelina turned up at the BAFTAs in a matching tux; and totally stole his style thunder.



Quite possibly the nicest example we’ve had of flawless tomboy style in recent times comes in the form of Emma Watson in a Saint Laurent Le Smoking ensemble. Finished off with a pristine white shirt, silver box clutch and black heels, it’s faultless.

Too-cool-to-care Cara looks stunning in her blue Mulberry tux at the launch of her named line of bags for the brand.

Monochrome and tuxedo suits sum up singer Janelle Monae’s unique style – it’s a polished take on tomboy that’s refreshing on the red carpet.

Rita Ora can often be found wearing flirty, feminine combinations or sports luxe separates, so it came as a little bit of a surprise to see her kitted out in this boyish yet impeccably tailored trouser suit in April. Teaming the all-white look with a fitted blouse, a clutch of gold rings, a red lip and a slicked back ‘do, Rita nails the sexy androgynous look with ease.

Back in No Doubt, Gwen Stefani was the quintessential 90s tomboy, hanging out with an all-male band and wearing low-slung jeans with vintage t-shirts ripped into crop tops, topped off with braces and some seriously experimental hairstyles. While she might have glammed up a bit since her No Doubt days, Gwen is still a huge fan of menswear-influenced style, and says she feels like a tomboy in a sea of other girlier pop singers: “I usually put pants on… I see these girls as more going for the sex-symbol thing…I was more, in the band, like a tomboy”

For a private screening of her new movie Love, Rosie, Suki Waterhouse chose a cool cream trouser suit which she paired with box fresh Superga platform trainers. This tomboy style ensemble is a fun change of style direction from the star who normally favours a girly dress and heels combo.

Ellen Page kept it classic and cool on the red carpet in a suit, white shirt and tie.

Who wore the trousers during the Golden Age of Hollywood? Katherine Hepburn did. Daring to wear pants when her colleagues would stick to dresses with cinched in silhouettes, Hepburn marked herself out as a fierce leading lady with her wardrobe of loafers and wide-legged slacks.

Emily Blunt looked incredible in a black suit and sheer blouse at a Vanity Fair event.

Hanging out at the NYC premiere of While We’re Young, Dree Hemingway looked every inch the tomboy style icon – she’s even pulling off a pipe tie for goodness sake.

Swapping her usual girly get up for a tailored trouser suit, we think Bella Thorne needs to channel androgynous more often. Take notes on accessories: stacked rings, open toe stilettos and a swipe of rose lippy will add a welcome softer edge.

Arguably the tomboy style icon of the noughties, Alexa Chung pretty much kick-started countless trends that sprung from menswear (and her personal tomboy style icons like Jane Birkin and Francoise Hardy) – from brogues and satchels and Breton tops, to dungarees and navy peacoats. In fact, the reason Mulberry created a bag in her honour was because she was wearing a men’s satchel by the brand on the red carpet.

Elizabeth Olsen, who also attended the event, looked great in some black straight-leg trousers and a navy trench.

Working off-duty tomboy well, Annie Lennox’s daughter – Tali Lennox shows how good pairing a feminine beauty look with a androgynous outfit can look. Where can we get her dungarees, please?

Singer Charlie XCX rocked a trouser suit and hence became one of our tomboy style icons!

Fearne Cotton isn’t a woman who shies away from switching up her style. One day it’s pretty sun dresses, the next it’s dark and edgy separates. Her latest home-to-work style is definitely more in the vein of the tomboy; long-length black blazer, buttoned-to-the-neck shirt, skinny jeans and tough-talking boots. It works perfectly.

We love this fussy bow and tux look on Ashley Benson. Whilst it’s very wintery and dramatic, this is one way to ramp up the glam factor on the red carpet.

Carly Rae Jepsen, where have you been and where have you been hiding these great dungarees? Nailing tomboy with her outfit and those brogues, the singer should style this look more often.

Touching down at LAX, Kate Upton had eschewed her usual form-fitting looks in favour of this formal tailored look. We’re loving those plush printed trousers.

Diane Kruger absolutely bossed the feminine tomboy look at a Ralph Lauren event in New York. We LOVE the braces and high-waisted suit trousers paired with her feline eyes and flowing locks.

For the 2015 Golden Globe Awards, Lorde opted for a Narciso Rodriguez suit, which she teamed with a crop top, slicked back hair, and diamonds. We’re loving your look, Lorde!

British beauty Felicity Jones is renowned for her retro elegance when it comes to dressing for the red carpet, but she was clearly in the mood for something completely different for her appearance on The Jimmy Fallon Show in November. The actress switched up her girly style in favour of this slick androgynous trouser suit, complete with tie. Proof that ornate dresses are not Felicity’s only fashion win.

We love the sleek androgynous vibe and model Coco Rocha completely nailed it at New York Fashion Week in September in this luxe pink trouser suit laden with glitter. The sharp blunt bob and dark make-up tones added extra punchy drama to the look.

Oscar winner Anne Hathaway often presents a very feminine fashion aesthetic for public appearances, but her latest outing marks a notable change in direction. For a charity event in LA, the 31-year-old teamed moody separates with an embellished slim-fit blazer, which worked in perfect harmony with her choppy cropped hair. Is this the start of a new style chapter for Anne now that she and her stylist of ten years Rachel Zoe have reportedly parted ways? Either way, it’s working.

It’s no surprise that Lou Doillon, the daughter of Jane Birkin, has nailed tomboy style, albeit with a more rock and roll take on the look than her mother. Lou’s staples are fedora hats, skinny jeans and ankle boots, with a mussed up ‘do and leather jackets thrown in for good measure.

Anyone who has seen Annie Hall will tell you Diane Keaton was the quintessential tomboy in the 1970s – her love of menswear (think wide-legged trousers, waistcoats and hats) in the iconic Woody Allen film made her a byword for borrowed-from-the-boys style.



Ask any girl with a pixie crop who inspired her to go for the chop, and she’ll probably reference Jean Seberg at least once. The American-born actress was the queen of the French New Wave films in the 1960s, and her style – slouchy, rolled up denim, striped t-shirts and over-sized knits – was the perfect partner to her boyish crop.

Just as we’re about to embrace our inner spring girl, Emma Stone steps out wearing this. The actress, who is in London to promote her new movie, The Amazing Spider-Man 2, looked incredible as she took to the streets of the capital in a mannish tweed suit and heels and a buttoned white shirt. A look we’ll be copying pronto, spring or otherwise.

OK, you might be thinking “How can a woman known for her bum selfies be considered a tomboy”, but Rihanna is the quintessential urban tomboy, switching from baggy baseball shirts to a slouchy menswear-inspired suit in the flash of an Instagram snap – and her collections for River Island have always featured boyish camouflage

Regularly cited by Alexa Chung as a style icon, the singer, model and 1960s muse Francoise Hardy was the queen of Parisian chic, friends with Yves Saint Laurent and Paco Rabanne and described by Mick Jagger as “his ideal woman” – and she did it all with a dash of tomboy style. Her love of Breton t-shirts and winged eyeliner was coupled with mod caps, slouchy trousers and oversized overcoats.

Combining androgyny with glamour, Marlene Dietrich wore masculine three-piece suits and an impressive array of hats, from fedoras to berets.

Salma Hayek‘s signature style normally consists of ultra feminine body-con dresses that accentuate her enviable curves. For the Yves Saint Laurent men’s collection show in Paris in January, she switched things up with a striking navy suit and tie, complete with a smart up-do and silver clutch. Suits you, Salma.

Ellie Goulding has often described her style as “tomboy” in spirit – and whilst she does wear the odd sexy showstopper like Roberto Cavalli or Julien Macdonald, it’s her love of denim shorts, cool slogan tees and grungy touches like pink hair and holey knits that her fans love.

Charlotte Gainsbourg

Tomboy style really DOES run in the family – because Jane’s other daughter (and Lou’s half sister) also makes our list for her casual cool wardrobe and tendency to go more off-duty than uber-glam on the red carpet.

Debbie Harry’s kick-ass punk style made her queen of the New York scene in the 1970s – vintage t-shirts and leggings, beanie hats and double denim were her takes on tomboy style.

“As far as I’m concerned, being any gender is a drag” said style icon and 1970s punk rocker Patti Smith. This pretty much summed up her androgynous approach to fashion –she would swap clothes with the artist Robert Mapplethorpe, and became known for her love of loose neckties, shirts and blazers.

Freja Beha Erichsen is the Danish model with the enviable off-duty style, adored by designers from Alexander Wang to Karl Lagerfeld. Her signature aesthetic consists of black skinny jeans, slouchy t-shirts, hoodies, leather jackets, and a growing collection of tattoos.



Isabel Marant‘s own brand of Parisian chic has definite tomboy credentials – it’s the effortless, slightly rock’n’roll styling of her leather trousers, sporty separates and bohemian pieces made for casual dressers.

The queen of 1960s free-spirited style, Jane Birkin inspired a Hermes bag now coveted by the A-list – but her REAL fashion legacy was her bohemian attitude to getting dressed in the morning. From shirts and ties, to boyish jeans and caps accessorized with a straw basket, Jane has said of her look: “Everything I wear doesn’t put me in the league of women. If I were a boy, I could look a lot prettier than a lot of boys I know”

A huge fan of Doc Martens and androgyny, when Agyness Deyn burst onto the fashion scene with BFF Henry Holland, we were at once fascinated by the Brit it model’s wardrobe – especially when she fully embraced menswear on the red carpet.

THE face of the 1960s, supermodel Jean “The Shrimp” Shrimpton may have often gone for a ladylike look, but she could also play the tomboy, as seen in many of her off-duty looks, including this corduroy suit worn with a tie and boots, worn in front of a stable on her farm in England.

Jenna Lyons

The woman behind J Crew has made us want to wear men’s striped shirts, boldly coloured trousers and knits, and suits all the time.

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