By Bianca Asare
Published Oct 26, 2026
2:50pm
Consider us bob aficionados, always on call to report back to you when celebrities and it-girls go for the big chop. This summer was lob season, with Hailey Bieber, Scarlett Johansson, and Ella Bright all embracing the versatile, not too long but not too short style. If you thought the short hair reign was only for spring and summer, though, think again—Ariana Grande and Billie Eilish are Exhibit A and Exhibit B. The two pop stars debuted flippy bobs on the same exact day last week in a pop culture moment that felt serendipitous, cosmic, and ultimately like a sign from above.
Grande’s bob felt more retro and distinctly flippy, a trend that we’ve already predicted for this winter. “We’ll be seeing chin-length bobs with flipped-out ends and lots of bounce,” celebrity hairstylist Clayton Hawkins says about the vintage-inspired flippy bob trend. “It’s a little retro, a little cheeky, and so easy to dress up.”
Eilish’s bob featured a more subtle flip. It’s more edgy, it features soft layers, and is complete with a ’90s-inspired blowout finish. And for Eilish, hair length isn’t the only thing she experimented with this fall—she simultaneously debuted a new auburn hair color that feels quintessentially autumnal.
The fall flippy bob trend is an extension of our collective nostalgia. From low-rise jeans to pastel eyeshadow, we’re drawing fashion and beauty inspiration from eras past. The flippy bob is versatile: polished and chic on Ariana Grande, and perfectly textured on Billie Eilish. We would also argue that the length and the way it allows scarves, high-neckline knits, and bundled-up coats to shine make it perfect for fall and winter.
