Miley Cyrus Makes Wearing Custom, Vintage & Runway Look Effortless For ‘SNL50’

Miley Cyrus wore three looks in one night at the Grammys — including her “sickening” custom Alaïa dress — and, in doing so, set the tone for her fashion mood in 2025. Her hair is now in a hime cut and slightly blonder, and her style energy is all-black, mostly vintage, and, yes, sickening indeed. She was in New York over the long weekend for the SNL50 extravaganza and wore four different outfits that show off not only her stylist’s extensive vintage-showroom Rolodex, but her goth-rock obsession and killer bod.

For the SNL50 concert on Feb. 14, she hit the red carpet before her performance in a Roberto Cavalli Spring/Summer 2025 dress with an asymmetrical mermaid hem and cutout pattern. For the stage, she slithered into another Cavalli confection — this one from the Spring/Summer 2004 runway — to open the show with Brittany Howard singing “Crazy Little Thing Called Love” and “Flowers.” Not only did she get the room on their feet with ad-libs in “Flowers” urging everyone to sing along, she set the tone for the weekend with two frocks from the same brand, designed 21 years apart, yet in perfect conversation with each other with slashes and a fringed hem done two ways.

The glam-rock energy continued on Sunday evening, when the stars amassed yet again on 50th Street in Midtown for the live show honoring 50 years of Saturday Night Live. For the red carpet, Miley opted for another archival ‘fit, this one from camp master Jean Paul Gaultier. Her one-shoulder suit-dress hybrid was plucked from the Spring 2009 Couture show and captures the essence of Gaultier’s cheeky take on sexed-up feminine menswear. Her last outfit change of the weekend came for her performance with Howard of “Nothing Compares 2 U” in a custom purple Gucci sequined halter-neck dress (another one to add to our trend-spotting tally), worn with a shearling boa for optimal drama.

She’s probably exhausted after serving so hard this weekend (who wouldn’t be?), and is giving us lots to think about for what we expect from stars at events. (We aren’t surprised that Miley wears fashion this well — remember her Bob Mackie at the 2024 Grammys?) She switched up eras, flexing in two brand-new pieces and two early-aughts gems while still making them her own and teasing what’s to come from her this year. It’s relatively easy to pull a vintage piece these days, with archives on Instagram helping stylists to make it happen, but to pull off these old dresses and wear them in a genuinely new way is a feat. The Oscars red carpet needs you, Miley!