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1
Prince (musician)
Born
Prince wore heeled boots, ruffled shirts, lace and cropped jackets to awards shows from the 1980s onwards, and his yellow lace trouser suit with cut-out seat at the 1991 MTV Video Music Awards is still one of the most cited menswear moments on any red carpet. Much of his wardrobe was made to order by a small in-house team, and he treated every appearance as a costume decision long before stylists made that standard for men.
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André 3000
André 3000 spent the Outkast years mixing argyle, kilts, platinum wigs, jodhpurs and golf caps at award shows, most memorably across the 2004 Grammys, where Outkast won album of the year. He treated preppy and country-club menswear as raw material for something theatrical, and his later choice of a jumpsuit and a flute on red carpets kept that independence going.
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Pharrell Williams
Born
Pharrell wore an oversized Vivienne Westwood "Mountain" hat to the 2014 Grammys and a tailored shorts suit to the Oscars a few weeks later, and has since worn Chanel tweed, pearls and jewelled sunglasses to formal events. His long run of genre-blending red-carpet choices led directly to a design career, and since 2023 he has been men's creative director at Louis Vuitton.
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Jared Leto
Born
Leto became Alessandro Michele's most visible male ambassador at Gucci, wearing long hair, floral and embroidered suits, capes and pussy-bow blouses to premieres and award shows in the late 2010s. At the 2019 Met Gala, themed on camp, he wore a red Gucci gown hung with crystal chains and carried a replica of his own head, echoing a Gucci runway show; his 2023 appearance dressed as Karl Lagerfeld's cat Choupette shows the same taste for spectacle, which divides opinion but kept pushing what men wear.
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Jaden Smith
Born
Jaden Smith wore skirts and dresses to proms, premieres and public events as a teenager in the mid-2010s, and in 2016 appeared in a Louis Vuitton womenswear campaign for designer Nicolas Ghesquière. At an age when most young actors wore safe suits, he made gender-neutral dressing part of his public image, which pushed fashion media to treat it as more than a stunt.
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Jonathan Van Ness
Born
Van Ness, the grooming expert from "Queer Eye", has worn ball gowns, sequinned dresses and heels to the Emmys and other awards nights since the show's success from 2018. As a non-binary public figure on mainstream television red carpets, they helped make gowns on people expected to wear tuxedos an ordinary sight at events where they had been rare, and they talk openly about those choices in interviews.
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Billy Porter
Born
Porter's black velvet tuxedo gown by Christian Siriano at the 2019 Oscars, styled by Sam Ratelle, is the single most discussed men's red-carpet outfit of the decade. He followed it with a series of planned looks, including being carried into the 2019 Met Gala on a litter in a winged gold outfit by The Blonds, and has been open in interviews about choosing gowns to challenge expectations of how Black gay men can appear in public.
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Harry Styles
Born
Working with stylist Harry Lambert and Gucci's Alessandro Michele, Styles moved from One Direction's skinny suits to pussy-bow blouses, pearls, flared trousers and painted nails. He co-chaired the 2019 Met Gala in a sheer black Gucci jumpsuit with a single pearl earring, wore a green feather boa to the 2021 Grammys, and in 2020 became the first man to appear alone on the cover of American Vogue, wearing a dress.
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Lil Nas X
Lil Nas X treats each red carpet as a staged reveal: a pink Versace cowboy outfit with harness at the 2020 Grammys, then at the 2021 Met Gala three Versace layers, a gold cape over gold armour over a jewelled bodysuit, removed one by one on the steps. Working with stylist Hodo Musa, he has made playful, openly queer camp a regular part of the men's red carpet rather than a one-off.
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Timothée Chalamet
Born
Chalamet's long collaboration with stylist Taylor McNeill and designers such as Haider Ackermann has produced some of the most influential men's red-carpet looks of recent years, from a sequinned Louis Vuitton harness at the 2019 Golden Globes to a backless red halter top by Ackermann at the 2022 Venice Film Festival. He shows how a leading man can push cut and fabric while staying recognisably elegant, which has made him a model for younger actors.
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Dan Levy (Canadian actor)
Born
Levy has used red carpets to put craft and art at the front: at the 2021 Met Gala he wore a Loewe outfit by Jonathan Anderson built around the work of artist David Wojnarowicz, with an image of two men kissing across the torso. At awards shows he has favoured unusual tailoring, embroidered jackets and statement shoes, showing that a menswear look can carry a point of view without abandoning the suit.
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ASAP Rocky
Born
A$AP Rocky arrived at the 2021 Met Gala wrapped in a puffy patchwork quilt coat by Eli Russell Linnetz's label ERL, remade from a thrift-shop quilt and now in the Met's own collection. Two years later he wore a tartan kilt and hoodie with his tailoring at the 2023 Met, and in 2025 he co-chaired the Met Gala devoted to Black menswear, "Superfine", a sign of how far his mix of streetwear, tailoring and unexpected fabrics has moved into the fashion establishment.
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Bad Bunny
Born
Bad Bunny wears painted nails, skirts and pearls as a matter of routine, and at the 2023 Met Gala he wore a custom white suit by Simon Porte Jacquemus, cut away at the back and trailing a train of white flowers reported at 26 feet. Because his audience comes from Latin trap and reggaeton, scenes with conservative ideas about masculinity, his consistent experimenting has carried the conversation to fans who rarely see it on Hollywood red carpets.
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Colman Domingo
Born
Domingo, styled by Wayman Bannerman and Micah McDonald, built a run of awards-season looks around colour, texture and jewellery, from Valentino capes and sheer fabrics to custom Louis Vuitton at the 2024 Oscars, where he was a best actor nominee for "Rustin". He co-chaired the 2025 Met Gala on Black menswear, and his choices show that bold dressing is not reserved for young pop stars.
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Lewis Hamilton
Born
Hamilton has used fashion events alongside his racing career for more than a decade, wearing skirts, sheer shirts and heavy jewellery, and in 2021 he bought a Met Gala table for young Black designers. As a co-chair of the 2025 Met Gala, "Superfine: Tailoring Black Style", he wore an ivory Wales Bonner suit with coattails and a Stephen Jones beret, styled by Eric McNeal, citing Cab Calloway as an inspiration.
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