Forget what it’s called, menswear hasn’t just been for the men for many decades.
From sleek tuxedos for women to nailing the oversized look for a powerful silhouette, it’s not unusual or unexpected for the traditional glamorous gowns of the red carpet to be replaced by something with more structure and strength.
Revisit some of the best examples of the biggest stars making the case that menswear is for all.
The greatest menswear inspired moments on the red carpet and beyond
Julia Roberts
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Julia Roberts didn’t just have an inspired menswear moment, she might have had *the* menswear moment.
At the 1990 Golden Globes, with Julia’s star on the rapid ascent after starring in hits like Steel Magnolias and Pretty Woman, the icon surprised everyone with her choice of oversized Armani suit.
As she’s told it herself, Julia spotted the Armani suit at the designer’s boutique on Rodeo Drive in Beverly Hills and stopped in to have it tailored. She has described the suit as one of her “all-time favourite outfits”, telling Vogue, “I could not have known that it was going to become this, like, statement outfit. I just thought I looked fabulous, and I still have that suit.”
Gwyneth Paltrow
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Showcasing her forward-thinking style even back in 1996, Gwyneth Paltrow wore what would become one of her all-time greatest looks with this iconic ruby-red suit designed by Tom Ford for Gucci. She later rewore the same suit in 2011, proving we really should keep hold of our clothes.
It was a merging of fashion and Hollywood that wasn’t necessarily the done thing at the time, with the stars of the 90s typically preferring a scaled-back look.
Gwyneth looked chic and relaxed but still sharp thanks to the inspired touches, like the peek of the periwinkle blue cuff and just enough bust on display for a subtle femininity.
Marlene Dietrich
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No list of women wearing menswear would make sense without the screen legend Marlene Dietrich.
Star of classics like Witness for the Prosecution and Morocco, Marlene, the queen of dressing like a king, was one of the pioneers of women embracing menswear as part of her bigger impact in addressing gender stereotypes.
Marlene famously wore a full tuxedo in 1930s Morocco, where she also shared an on-screen kiss with a woman. This was when women and moral codes were much stricter, so Marlene’s tux and tradition-kicking is to be respected.
Nicole Kidman
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A fashion icon who can switch seamlessly between Old Hollywood glamour and on-trend looks, Nicole Kidman put her own flair on menswear at the 2025 premiere of Nine Perfect Strangers.
Nicole proved that menswear doesn’t need to come without panache and glamour, looking striking in a boxy, form-fitting suit that was made from a glittering fabric.
Skipping a shirt for a more flirtatious touch, Nicole also added the fashionable touch of a white floral brooch and white cuffs to enhance her proportions and create some contrast.
Angelina Jolie
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Angelina Jolie didn’t just channel menswear at the 2014 BAFTAs, she evoked the swaggering, suave spirit of the Rat Pack.
Looking like she’d just finished a set with Frank Sinatra, Angelina looked perfectly unkempt with an unfastened bow tie, rolled up sleeves and spread collar. Angelina’s look was a custom Saint Laurent.
Celine Dion
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Celine Dion’s best looks prove that the singer always hits the right notes when it comes to fashion, and in 1999, she showcased that she can even put her own remix on menswear.
An oversized white silk suit (designed by none other than John Galliano) worn back-to-front (and with a matching oversized fedora), Celine’s backwards-suit was universally panned at the time.
However, with time, people have come to appreciate the unique, unforgettable take on glamorous menswear.
Diane Keaton (Annie Hall)
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There’s perhaps no greater example of a woman claiming menswear as her own than Oscar-winning legend Diane Keaton. From her personal red carpet appearances to her everyday wear often shared on her Instagram, Diane’s aesthetic has stayed the same since 1977’s Annie Hall.
In the classic, Diane is credited for creating most of her character’s iconic looks, made up on oversized trousers, waistcoats, oversized ties and other menswear staples.
Kate Winslet
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A suit doesn’t necessarily always have to be menswear – women have tailors too! – but Kate Winslet’s choice of subtly oversized suit to the 2025 Golden Globes was an inspired combination of traditional men’s silhouettes with more flair and design.
The Titanic star’s cream suit popped on the red carpet, thanks to its wide-legged silhouette and black floral illustrations on the blazer.
Blake Lively (A Simple Favour)
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2018’s A Simple Favour and the 2025 sequel, Another Simple Favour, are twisty, stylish thrillers well worth a watch. But even if you’re not interested in the storyline, Blake Lively’s endless parade of inspired, reimagined menswear looks makes it a fashion masterpiece.
From pinstripes to waistcoats, trilby hats, and cummerbunds, Blake’s character makes menswear her staple, and it might just have you wanting to try a look for yourself.
Andie MacDowell
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Four Weddings and a Funeral actress Andie MacDowell shut down the Cannes red carpet in 2025, swapping dresses for a sharp, tailored black tuxedo.
Pairing menswear staples with her own feminine flair, Andie’s suit included intentional touches like a sleek satin collar and an oversized velvet bow tie.
Extra style points for her, she flipped her curls up for a shorter do, complete with a sweeping, floppy fringe.
Madonna
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When it comes to classic menswear and tailoring, men know to turn to Ralph Lauren. And, as it turns out, so do the women.
Queen of Pop Madonna wore a custom three-piece Ralph Lauren tuxedo, complete with a stylish cane and a wide-brimmed hat for added drama.
The chunky tie and the crucifix were classic Madonna touches to switch up a traditional black tie look.
Cynthia Erivo
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Cynthia Erivo added her own flair to a classic pinstripe suit as she shut down the red carpet of the NAACP Image Awards.
Cynthia’s Dolce & Gabbana pinstripe suit was fitted to perfection, with the buttoned jacket cinching in at the waist and the oversized trousers giving more drama and glamour.
Her smattering of brooches on the lapel proves how easy it is to reinvent a classic menswear look.
Ana de Armas
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A three-piece suit worn to perfection, Blonde star Ana de Armas opted for a monochromatic navy look at the premiere of Netflix’s The Gray Man in 2022.
A three-piece suit can sometimes overwhelm if not fitted correctly, but Ana cleverly sidestepped this through her choice of going shirtless and wearing a statement necklace.
America Ferrera
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By 2024, Barbie star America Ferrera might have been tired of all the pink, which could explain her choice of a classic tuxedo for the Academy’s Governors Awards.
Keeping her tuxedo traditional, America’s relaxed, wavy hair added a touch of relaxed cool, and her pop of red nails stood out against the black and white ensemble.
Diane Keaton
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Diane Keaton has worn many menswear looks in many forms, but she showed she still finds new ways to put a spin on it when she attended the 2021 LACMA Art+Film Gala.
Diane wore a dark blue sequined Gucci blazer over a white button-down shirt (with an oversized collar), paired with matching sequined pants and a black beret.
Winona Ryder
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Not all menswear-inspired looks have to be uber formal or reminiscent of James Bond, as Winona Ryder showcased expertly in the 1990s.
The always-chic star of Beetlejuice was snapped making her way to a premiere wearing a louchy, oversized jacket and wide-legged trousers. Underneath, she went with a scoop-necked, sateen-looking shirt tucked into a black belt.
Nicole Kidman
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Proof that styles always come around again, Hollywood icon Nicole Kidman stepped out on the 2025 Critics’ Choice Awards in a look that was reminiscent of Julia Roberts’ oversized suit from 1990.
The Moulin Rouge! star wore an oversized Saint Laurent suit in a neutral cream colour paired with a light blue striped shirt and a wide, navy polka dot tie.
Cate Blanchett
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Oscar-winning actress Cate Blanchett proved that menswear silhouettes don’t have to stick to rigid colours when she walked the carpet of the 2024 Venice Film Festival.
Cate had fun with her boxy, slightly oversized Moschino suit, which featured massive, white polka dot prints.
Blake Lively
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Even the most dapper of men might struggle to pull off a three-piece, white, pinstriped suit, which makes it oh-so impressive that Blake Lively made the look entirely her own.
Underneath her pinstripe waistcoat, Blake swapped the traditional white shirt for one with lacy sleeves and rouched detailing.
Emma Stone
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Emma Stone’s look for the Los Angeles premiere of Cruella in 2021 proved the power of playing with some menswear separates.
Emma paired a dark blueish, oversized blazer with a pair of wide-legged black trousers. Tying the separates together, Emma’s white bow neck shirt added a touch of glamour.
Princess Diana
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The 80s were all about power dressing – big shoulders, big colours, big hair. So it’s no surprise that, when pregnant with Prince Harry in 1984, Princess Diana used the opportunity to swap her ballgowns and form-fitting gowns for a classic white tuxedo, designed by Margaret Howell.
The white jacket offered the pregnant princess a comfortable, stylish silhouette, and the silver lapels and oversized black bow tie allowed for contrasts.
Blake Lively in Versace menswear
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Blake Lively proved that she makes her own fashion rules as she stepped out in New York City wearing a bold, highlighter-green look that wasn’t just inspired by menswear, it was right from the menswear runway.
Blake’s neon green combination – including jacket, trousers and pointelle-knit jumper – was plucked straight from the runway of Versace’s Spring Summer 2019 menswear show.
Sarah Jessica Parker
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When Sarah Jessica Parker returned as the iconic Carrie Bradshaw for And Just Like That, fans were eager to see how Carrie’s unique style would’ve evolved and adapted to her next stage in life. And she didn’t disappoint.
In one episode, Carrie shows how to do stylish and statement-making in a subtle, classic way, going for a matching oversized burgundy suit jacket and wide-legged trousers, paired with a simple black top to not distract from the boxy silhouette.
Monica Bellucci
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Screen legend Monica Bellucci made a case for adding flair – or should that be, flares – to a staple menswear look while attending the 2024 Emmy awards.
Monica, pairing her classic tuxedo suit jacket with a white ruffled shirt, bow tie and cummerbund, finished her Saint Laurent look with the most dramatic bell-bottom flares.
Cara Delevingne
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Cara Delevingne’s unforgettable menswear-inspired look was one of the most talked-about outfits from Princess Eugenie’s 2018 wedding to Jack Brooksbank.
The model-turned-actress chose a perfectly tailored Emporio Armani tuxedo with cummerbund, tails, stilettos and top hat to the ceremony at St. George’s Chapel.
Demi Moore
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Demi Moore is proof that menswear-inspired looks can make relaxed, more laid-back styles look intentional and chic.
Pairing a suede jacket over a bow-neck blouse and with baggy jeans, Demi avoids looking like she’s underdressed thanks to the inspired choice of textures and proportions.
Aubrey Plaza
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Parks and Recreation actress Aubrey Plaza brought elevated menswear to the 2023 Film Independent Spirit Awards, pairing a structured, oversized suit jacket with dramatic, wide shoulders with loose, relaxed trousers.
The contrast of the sharp, square shoulders with the subtlest hint of skin as she skipped a shirt stopped this look from feeling overwhelming or costume-esque.
Bianca Jagger
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Bianca Jagger has been making menswear her own since the days of Studio 54, and she’s still rocking it to this day.
Bianca often relies on suits and chic tailoring for her appearances, and she famously wore a Saint Laurent blazer instead of a white dress on her wedding day in 1973. Radical for the ’70s, and it would still be considered a bold choice by some today.
Kourtney Kardashian
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What’s the best accessory for a menswear-inspired, chic black tux? A husband matching in his tux.
Kourtney Kardashian and Travis Barker twinned on the 2024 Emmys red carpet, both wearing tailored black tuxedo jackets with satin lapels. Kourtney added a touch of glamour to hers by ditching the undershirt and opting for a bralet.
Katharine Hepburn
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She holds the record for the actress with the most Oscar wins of all time – winning four times – but that doesn’t mean Katharine Hepburn bought into the stereotypical idea of Hollywood glamour.
In fact, Katharine was a pioneer for menswear, choosing to wear men’s jackets and trousers at a time when it was, if you can believe this, illegal. Women could be arrested for wearing long trousers in public in the 1930s, but she kept at it.
Grace Jones
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Singer/actress/model/icon Grace Jones has always done things her own way, but her early embracing of menswear and androgynous looks was particularly revolutionary and forward-thinking in the 70s and 80s.
Grace’s uniform often included sharp, tailored suits, oversized blazers (often worn without anything underneath), and structured silhouettes that captured her unique recipe of strength and seduction at the same time.
Janelle Monae
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Singer and actress Janelle Monáe has become something of the Katharine Hepburn/Marlene Dietrich/Grace Jones of her generation, making suits – from the straightforward to the avant-garde – her signature.
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