Every Early 2000 Britney Spears Outfit From Her 'Oops..' Era Music Videos

When Oops...I Did It Again hit stores 15 years ago, it marked a new era for Britney Spears, and indeed the world. The pop princess was blossoming from an over-sexualized Lolita to an over-sexualized young lady. School girl uniforms were tossed out for red sex suits, and the universe sang loudly, "It's 2000, everyone!" And you can tell from those "Oops...I Did It Again" era videos just how 2000 it was... those outfits are a dead giveaway

Maybe we're just not ready yet for the 2000 revival of fashion... haven't the '90s been coming back for the last five years? But in any case, Britney's outfits are kind of hilariously dated, either as a marker of the year, or as a side affect of the time. That element of being so cringeworthy is what made me want to power through those music videos and relive the crotch-lacing. And now you can too!

To celebrate how much time has passed since the era of "Oops...I Did It Again," we've captured all of Britney's video outfits for your visual enjoyment. Some you will undoubtedly forgive as a nostalgia-laden classic. Other outfits... will be a lot harder to forgive. Have a blast either way!

"Oops...I Did It Again"

Ah, the red pleather catsuit. It's not necessarily like we were all buying these all up at Delia's, or anything, but like it was a game changer of an outfit. Shiny red leather (PVC?) was somehow an accessible thing we can wear now. Hell, I had some red pleather pants in 4th grade. Why my mother let me wear them, I still don't know.

This catsuit also popped out in a lot of cartoon doll makers, too. Weird.

Though a fairly basic, monochromatic outfit, it seep it's early 2000s cred for showing about 11 inches of stomach. Even as we scramble desperately to bring on a crop top revival, nobody's walking around in a turtleneck that barely passes our boobs. Props for the lack of shoes, though, a good foreshadowing of the Cheetos-and-Starbucks Britney we'd see in gas stations everywhere during 2005.

And finally, this underwhelming piece of work. Not much to say except it acts as an extension of the PVC-phase of this era, with tight, shiny, plastic-y leather dominating instead of the a-line, matte "leather" skirts that populate Forever 21 these days.

We also don't accessorize with Astronauts anymore. Spacemen are SO passe.


Unnecessary lacing was weirdly big in the late '90s and early 2000s, and to this day I'm not quite sure why. What look are we going for, here? The Game of Thrones line for Limited Too? It's certainly not a tragic look, but it would warrant a side-eye if someone wore it today.

THIS, is decidedly, more tragic; that is most definitely crotch-lacing over there, people. If you're not like, a lost member of Fleetwood Mac, I'm fairly sure you're not able to get away with that crotch-lacing. It's just impractical and sad and makes me feel all kinds of uncomfortable.

She also has a bunch of stupid bracelets on, as is tradition in 2000-something. But let's take another closer look at that crotch-lacing.

My god. Lucky is having NONE of that.

Lucky's look isn't anything to write home about either, though. It's intentionally more of a take on Old Hollywood glamour with all those romantic slips, fuzzy robes, and wearing-diamond-necklaces to bed, but the make-up ruins it. Like, Marilyn Monroe would be appalled with that lipstick.

It's probably called "Iced Plum" or something horrendous.

And then there's this look, which part of me is in love with. The other part of me thinks it's about 50 shades of ridiculous. Squint hard and you'll see that she's wearing jeans under her dress, which was a cult early-2000s look more commonly worn by babygoths. Rest assured, the plaid dress and jeans look was my jam, so it's weird to see the princess of pop take on this early iteration.

The tulle isn't really indicative of any era, but the propensity for glitter definitely screams "It's the new millennium, ya'll!"

Lucky, again, is trying to give off a vintage vibe, but it's ruined by the cheap shinyness of her dress. She looks less like Veronica Lake and more like a holographic Pokemon card, which, in its way, is VERY 2000.

Psyched because she's two levels away from evolving into Madonna.

Actual Britney is weirdly reaching out to her, wearing a turquoise velveteen halter top with a gaping hole in the middle. It's not even an aesthetic thing, it looks like it's an accident. Captain Peroxide to the right is weeping for all the crimes of fashion, not realizing he's 2000's biggest victim.

Update: though it's hard to tell, this may be a matching turquoise velveteen set. Will wonders never cease?


Oof. Here Britney is donning the deluxe version of that plastic tattoo choker we all use to wear. Plus she has a tacky skin decal, giving us serious Karen from Mean Girls flashbacks. It's not how you want to be seen when you catch your boyfriend with a robo-tramp.

Party on the top, travesty on the bottom. Don't think many people were mimicking this look in real life, but using a sliver of fabric to cover your va-jay seems very in line with that generation's pop music.

Sadly this is somehow one of Britney's less horrendous looks. Although the 11 inches of stomach? Still very 2000. And the feather trimmed flares? Not helping.

She blames the chair for this fashion mis-step, but she has nobody to blame but herself.

And finally: crimped hair. Raise your hand if you have at least one or two school photos with that disastrous look plaguing your head.

"Don't Let Me Be The Last To Know"

She just wears denim shorts and a beige bikini top here. Disappointing in so many ways.

Images: YouTube (13), Giphy (1)