From ‘90s to now: The best Britney Spears hair moments

Take a sip from this sweet cup of nostalgia

BEAUTYcrew Beauty Editor / April 14 2022

She’s an icon that has transcended generations not only for her music contributions to modern popular culture but also for her many (and I mean MANY) iconic moments of beauty and fashion. From large snakes to floor length denim ball gowns, when it comes to fashion choices, Britney Spears isn’t afraid to get a little crazy, instead choosing to anchor her more wild looks with classic hairstyles that evoke a pageantry flair that speaks to her Southern heritage. 

We can only hope that you follow Hailey Bieber’s example and start incorporating these timeless styles into your daily hair styling repertoire.

In honour of a woman so bold only she could burn down her own gym and call it an accident, (anarchic, pyromaniac Britney Spears is without a doubt our favourite brand of Britney Spears btw) and in the interest of our eight-year-old self, here is a list of some of the pop icon’s best hair moments throughout the years.

Hit Me Baby One More Time

We start where our obsession with Britney began, with the infamous ‘Hit Me Baby One More Time’ video. This clip is a smorgasbord of great hair moments; obviously those pigtails have transcended pop culture status at this point, but the humble half-up half-down, double ponytail look is undoubtedly the unsung hero of this whole production. Practical enough for the basketball court and a highly choreographed dance routine, this is the style that’ll have your back through a day full of errands and possibly a sweaty hot yoga sesh. Sorted.

Spears has even inspired the hair styling decisions of some of our other favourite celebrities. Case in point? Hailey Bieber hit us one more time with the ‘90s-era tomboy look that Spears was serving. Bieber sported a cutesy set of plaits that she debuted via TikTok:


If only we had a wind machine on-hand 24/7 to really pull off the full early noughties interpretation of the Farrah Fawcett flick that Brit’s got going on in the ‘Lucky’ video. Whether you’re suspended from a hula hoop or rolling around the back of a limo, the fanned out bob works for a myriad of occasions. If you’re feeling really funky and want to mix this one up a bit, layer a few chunky clips and pin back the fan. Did someone say cute?

Oops I Did It Again

We don’t know if it was the chunky blonde highlights, the bulky extensions, or the sleek, smoothed over side fringe that tickled our fancies as children, but to our eight-year-old selves the hair and makeup in the ‘Oops I Did It Again’ video was the height of fashion. Period. This is a statement we still stand by. 


Britney is channeling the unrivaled hairography skills of hair legends Stevie Nicks and Tina Turner in this one, whipping her voluminous, ‘80s-inspired bonnet across the floor as she angrily dances her way through a complicated chair choreo routine. Super easy to recreate at home - wind machine optional.

I'm Not A Girl, Not Yet A Woman

Ummm is it just us or is this video evidence that Britney actually invented the piecey lob? This is the height of understated cool, and probably the easiest style on this list to recreate, simply requiring a few texturising products. Add a few skinny braids at the front for a bit of a boho edge or a statement noughties-approved hat to mix it up.

Britney’s been using quarantine to switch up her look. She just covered her whole body in tattoos.

Main image credit: @britneyspears

Briar Clark got her start in the media industry in 2017, as an intern for Marie Claire and InStyle. Since then, her keen interest in fashion and beauty has landed her gigs as a Digital Content Producer and Beauty Editor with titles like Girlfriend, Refinery29, BEAUTYcrew and beautyheaven. She loves the way seemingly innocuous topics like skin care and style have the ability to put a smile on people’s faces or make them think about themselves a little differently. A big believer in self love and experimentation, Briar has made a point of becoming the Australian beauty industry’s unofficial guinea pig for unusual treatments and daring hair trends. When she’s not testing out the latest beauty launches, Briar is big on broadening her horizons, mostly in the form of food but she’s also partial to travelling to new destinations both near and far (and of course, allocating an extra bag to bring their best beauty offerings home with her).