Celebrities Who Nailed Humor and Style on the Red Carpet

As fashion writers, we often find our work simplified when a celebrity delivers a true red-carpet moment. Niche references abound, dramatic adjectives flow effortlessly, and there’s no shortage of technical details or trend analyses to delve into. However, when fashion meets humor on the red carpet, it’s the holy grail. Style can never resist a touch of silliness, and amidst the opulent glamour of gala-ready gowns and polished beauty, a tongue-in-cheek sartorial moment has the potential to go down in history—or go viral, if we’re addressing Gen Z—simply for being daring.

The Power of Humor in Fashion

History offers ample proof of this. From Britney Spears and Justin Timberlake’s iconic double denim ensembles that symbolized the tackiness of the Noughties, to Meg Stalter and Paul W. Downs showing up at the Critics Choice Awards as Kylie Jenner and Timothée Chalamet, there’s nothing the style set loves more than a touch of mimicry à la mode.

Runway Humor

Before dismissing this trend as an act of Hollywood-induced desperation to stay relevant, consider the runways. Designers like Jonathan Anderson have given us pixelated hoodies, goldfish dresses, and pigeon clutch bags at Loewe and JW Anderson. Viktor & Rolf translated their blunt sense of humor into a series of slogan tulle gowns for their 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.

2026 Trend Cycle

And it seems like humor has a place in the 2026 trend cycle too. According to Pinterest, consumers can expect excessive color, layering, and accessorizing this year. A retaliation against the influencer-approved ‘Clean Girl’ aesthetic, this upcoming penchant for maximalism will flood our feeds—so expect kitschy cool-girl pieces spanning fun gummy bear jewelry to slogans dripping in irony.

Top Red Carpet Moments

Let’s take a look at some of the top red carpet moments when stars embraced funny fashion for all to enjoy:

Kylie 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 Timothée’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.

Meg 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.

Justin 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.

Björk’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.

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 with high fashion. This look perfectly encapsulated Perry’s bold and playful style, making it one of the most memorable red carpet moments in recent history.