Miley Cyrus Stuns in Her Second Oscars Night Look at Afterparty

Miley Cyrus underwent a chic switch-up on Oscars night, debuting a bold look at the Vanity Fair afterparty after embracing Old Hollywood glam to present at the Academy Awards earlier in the evening.

The “Flowers” singer, 32, rocked bleached brows, micro bangs, and a long, slicked-back ponytail while sporting a black sheath gown by Maison Margiela. Cyrus kept the look simple with her chic silver hoops while walking the red carpet with her boyfriend, fellow musician Maxx Morando.

Cyrus had Morando, 26, by her side earlier in the evening as well, as she sported a classic custom black Alexander McQueen high-neck halter gown with lace gloves, which she paired with diamond earrings. The “Wrecking Ball” singer completed the classy look with voluminous waves, balancing out her edgy brows with a more Old Hollywood detail.

Cyrus and Morando have been dating since 2021, following the Grammy winner’s divorce from Liam Hemsworth. “He’s very similar to me. We just don’t take life too seriously,” Cyrus revealed to Harper’s Bazaar in November 2024, adding, “He looks at life really differently than I do. He grew up with a laptop. I had a desktop computer that I shared with my brothers and sisters. … Honestly, he’s raised our dog off Reddit. I’m like, Are you sure we’re supposed to be doing this? And he’s like, On Reddit it says blah, blah, blah.”

The “Used to Be Young” singer has kept her relationship largely out of the public eye, but told the outlet that she had been collaborating with her musician beau. “I worked with my dad forever,” she said of her history of working with loved ones. “That’s how me and my ex-husband met each other. I’ve always worked with the people that I love. And Maxx just inspires me so much.”