The Millennial Side Part Might Be Back, But These Y2K-Era Celebs Are The Blueprint

Join me, if you will, in 2021. The world is re-emerging from lockdown, Olivia Rodrigo has just burst onto the music scene, and everyone is watching Squid Game. And over on TikTok — the social media app that had blown up just a year earlier — a viral debate rages: Are side-parts painfully millennial? As would later be the case with topics as varied as jeans, mimicking a phone call, and brunch, the topic riled up the internet. But there is one undeniable truth: The early ‘00s (aka the Y2K era) was absolutely dominated by side-parted hairstyles.

That’s not to say there weren’t any center-parted (or even part-less) looks at the turn of the millennium. Indeed, one of the most famous xennials of all time, Britney Spears, gravitated towards center parts and choppy layers, as did millennial teen superstar Amanda Bynes. But for the most part, the Y2K era was as dominated by deep side parts and overdirected bangs as it was frosted makeup and velour tracksuits.

But don’t just take my millennial word for it. Scroll on to see some of the standout side-parted hairstyles from the Y2K era — defined here as the late ‘90s into the first half of the ‘00s — into the late aughts.

Sarah Michelle Gellar, 1999

Unsurprisingly, the 1st Annual Teen Choice Awards provided a treasury of Y2K hair inspo. First up: Buffy the Vampire Slayer herself, with pin-straight strands fully overdirected to the left.

Sandra Bullock, 1999

At the same event, Bullock — star of the following year’s Miss Congeniality — rocked a feathery, flippy lob that just had to be on Hailey Bieber’s mood board.

Lucy Liu, 2000

Months before the release of Charlie’s Angels, Liu paired cascading curls with slicked-down, side-parted bangs.

Aaliyah, 2000

The greatest to ever do it when it comes to the silk press, Aaliyah donned a deep side part and dip-dyed ends at the 2000 MTV Movie Awards.

Beyoncé, 2001

When Beyoncé co-hosted the red carpet pre-show for the 2001 MTV VMAs — yes, really — she went for tropical vibes, accenting her side-parted style with orchids.

Britney Spears, 2002

Though she actually side-parted less than you would think, Spears did shift her strands to the left for the 29th Annual American Music Awards, complete with a zig-zag part.

Lindsay Lohan, 2004

As one of the era’s biggest teen stars, Lohan didn’t just rock a side part — she arguably helped bolster its popularity in the first place. At the 2004 Kids’ Choice Awards, the star of Confessions of a Teenage Drama Queen opted for loose waves and a deep part to the right.

Mischa Barton, 2004

In the early ‘00s, Barton was practically synonymous with “Cali Cool Girl.” During that time, her side-swept bangs often accented effortless beachy waves.

Paris Hilton, 2004

No Y2K list of any variety would be complete without Hilton. A lifelong deep side part devotee, the reality star is still occasionally overdirecting to this day (albeit nowhere near as dramatically as she did in the aughts).

Nicole Richie, 2005

Somehow, Richie’s clavicle-grazing lob, winged eyeliner, and terracotta blush look as 2026 as they do 2025… deep side part and all.

Hilary Duff, 2005

As hard as it was to pick just one of Duff’s many side-parted styles, as soon as I saw this red-highlighted, pop-punk princess moment, the competition was over.

Christina Millian, 2006

After much research, I feel confident declaring Millian as the Queen of the Y2K Ponytail Bouffant. This chocolate, barrel-curled iteration is among her standout looks (of which there are many).

Selena Gomez & Taylor Swift, 2008

As Y2K came to a close — with the Swag Era on the horizon — millennial icons Selena Gomez and Taylor Swift attended the premiere of the latter’s film Another Cinderella Story in vaguely boho ‘fits and matching deep side parts.