Miley Cyrus Wore the Most Nostalgic Y2K Updo

No one does Y2K nostalgia quite like a Disney Channel alum, as Miley Cyrus just reminded us.

Cyrus appeared on Jimmy Kimmel Live! on December 4, and while her glittering maroon Tom Ford dress was right on theme for the holidays, her hairstyle stole the spotlight. Cyrus wore a high messy bun styled in signature “spiky” early aughts fashion. Most of her hair was slicked tightly to her head, except for a chunky face-framing layer which was pulled out to create a side-bang effect with her deep-side part. The contrast between the sleek exposed hair and textured bun gave major Lizzie McGuire vibes, and we’re absolutely here for it.

On the show, the singer discussed her new song “Dream as One” (which will be featured in the upcoming film Avatar: Fire and Ash) as well as some exciting personal updates: Earlier this week, she confirmed her engagement to drummer Maxx Morando after four years of dating.

Cyrus was earlier spotted en route to the studio, sporting her nostalgic hairstyle with some other Y2K-inspired silhouettes. She wore a bulky chocolate brown fur bomber jacket with slate gray flared leather pants. For accessories, she added a low-slung gold chain belt with a hefty heart-shaped charm and a matching necklace.

As far her piecey, pulled-out updo goes, we smell a celebrity trend. Kendall Jenner wore a softer version of the asymmetrical hairstyle this week for the L’Oréal Paris Women of Worth 20th Anniversary event in Los Angeles. While her styling was a bit less early 2000s-coded—a low, loosely pinned bun, middle part, and softer texture in the chin-length layer she left exposed on one side—the concept was quite similar.

Hailey Bieber has also been on an updo kick recently, pulling out long front pieces from her signature slicked-back styles to frame her face. While this styling is common for curtain bangs, which are typically too short to be pulled back with the rest of the hair, these celebs are intentionally leaving sleek, longer layers unswept.

The best part about this celeb-loved look—whether you’re aiming for Y2K realness or a more modern take—is how easy it is to recreate. The key is to preserve your part, especially in the front, when pulling your hair back. Carefully section the chunks of hair you want to leave down, and secure them with a blow-out clip, barrette, or scrunchie.

Then, style the rest of your updo as usual; using a mousse or a wax stick will help you perfect a uniform, tight slickback, which contrasts beautifully with your softer face-framing pieces and textured bun. Style your “bangs” last: For the Miley Cyrus look, hit them with a straightener in a uniform C-curve motion. For a softer version, you can use a curling iron and texture spray to add a soft wave.

Grace McCarty is the associate beauty editor at Glamour.