As fashion writers, our job becomes infinitely easier when a celebrity delivers a true red-carpet moment. Niche references come thick and fast, the dramatic adjectives write themselves, and there’s no shortage of technical detail or trend analysis to luxuriate in.
Yet, when fashion has a sense of humour on the red carpet? The holy grail. Style can never resist a touch of silliness. Inbetwixt the opulent glamour of gala-ready gowns, polished updos and flawless beauty blends, a tongue-in-cheek sartorial moment has the most potential to go down in the history books (or viral, if addressing Gen Z) - simply for being daring.
History offers all the proof we need here. From Britney Spears and Justin Timberlake’s iconic matching double denim ensembles, that came to symbolise the delicious tackiness of the Noughties, to Hacks' Meg Stalter and Paul W. Downs showing up to the Critics Choice Awards as Kylie Jenner and Timothée Chalamet last night, there’s nothing the style set loves more than a touch of mimicry à la mode.
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© GettyBefore dismissing the trend as an act of Hollywood-induced desperation to stay relevant, consider the runways. Jonathan Anderson gave us pixelated hoodies, goldfish dresses and pigeon clutch bags at Loewe and JW Anderson. Viktor & Rolf translate their blunt sense of humour into a series of slogan tulle gowns for the brand’s spring/summer 2019 haute couture ‘Fashion Statements’ collection. Moschino established fashionable food as a trend to watch, delivering spaghetti clutches, McDonald’s-inspired outfits and Spongebob Squarepants knits courtesy of Jeremy Scott.
And - it seems like humour has a place in the 2026 trend cycle too. According to Pinterest, consumers can expect excessive colour, layering and accessorising this year. A retaliation against the influencer-approved ‘Clean Girl’ aesthetic, this upcoming penchant for maximalism will flood our feeds thick and fast - so expect kitschy cool-girl pieces spanning fun gummy bear jewellery to slogans dripping in irony.
Check out the top red carpet moments when the stars embraced funny fashion for all to enjoy.
Funny fashion moments from the red carpet:
© Variety via Getty ImagesKylie Jenner and Timothée Chalamet's Matching Moment
Far from your regular matching moment, Kylie Jenner and Timothée Chalamet hit the red carpet to celebrate the premiere of Timothee’s new movie, Marty Supreme, in custom Chrome Hearts.
The pair turned heads as they posed for a selection of red carpet shots. Kylie leaned into her love for cut-out detailing, her orange leather dress fitting her physique like a glove. Timmy matched her look in a suave blazer layered over a silk shirt - cut from an identical zesty shade of traffic cone orange.
© Getty ImagesMeg Stalter and Paul W. Downs' Matching Moment Mimicry
Comedians Meg Stalter and Paul W. Downs arrived at the 31st Critics Choice Awards mimicking the outfits that Timothée Chalamet and Kylie Jenner wore to the Los Angeles premiere of Marty Supreme.
The Hacks stars posed on the carpet in their orange outfits, adopting the same pose as the A-list couple. While Kylie and Timothée wore custom orange Chrome Hearts, Meg and Paul's ensembles were created by LA based designer Erica D. Schwartz.
© WireImageJustin Timberlake and Britney Spears' Double Denim
Justin Timberlake and Britney Spears’ matching double denim at the 2001 AMAs paired her crystal-embellished, body-skimming gown with his custom patchwork denim suit, pearl snaps and cowboy hat.
Camp, coordinated and gloriously excessive, the stars' Y2K aesthetic distilled Noughties pop spectacle and endures as fashion’s most audacious (and diamanté-clad) red carpet power couple moment.
© WireImageBjörk's Swan Dress
Björk’s 2001 Oscars swan dress, designed by Marjan Pejoski, wrapped the singer in feathered fabulousness, complete with an egg-shaped clutch.
Equal parts couture and costume, the beaked look mirrored the Icelandic star's avant-garde onstage persona and cutting-edge look - one defined by unapologetic whimsicality.
© Getty Images for The Met Museum/Katy Perry's Chandelier Dress
Katy Perry’s 2019 Met Gala Moschino look was a literal chandelier, sparkling with crystal embellishments and oversized candle accents, that married whimsy and high camp. Paired with a glittering headpiece and a sculptural silhouette, the luminescent concoction perfectly captured the gala’s theme, Camp: Notes on Fashion, referencing Susan Sontag's iconic essay - the inspiration behind the star-studded bash.
© Getty ImagesJared Leto's Choupette Homage
Safe to say Jared Leto stole the show at the 2023 Met Gala, which celebrated Karl Lagerfeld: A Line of Beauty. Then-poised to portray the late Chanel creative director in an upcoming biopic, Leto made an unforgettable entrance, ascending the iconic Met stairs in a life-size costume inspired by the designer’s beloved cat, Choupette.
Bewildered spectators were left in awe of the furry costume until Leto removed the head of the extraordinary piece to reveal his identity.
© Getty ImagesLady Gaga's Meat Dress
Lady Gaga’s 2010 MTV Video Music Awards appearance remains one of pop culture’s most bizarre fashion moments. Draped entirely in raw beef, the dress, designed by Franc Fernandez with makeup by Nicola Formichetti, shocked audiences - particularly those of the veggie persuasion.
One of Gaga's many outrageous ensembles, the look cemented the singer's reputation as one of the weirdest and most wonderful talents in the music field.
© Jeff SpicerEmma Corrin's Goldfish Dress
One of our favourite red carpet looks to date, Emma Corrin's JW Anderson goldfish dress warrants icon status. Back in October 2022, the actor wore the graphic piece by JW Anderson to attend the European premiere of My Policeman at the Royal Festival Hall during the 66th BFI London Film Festival.
