Ranking Britney Spears' 'Oops!... I Did It Again' Music Video Outfits — Because She Helped Define The New Millennium's Fashion For Teens

Britney Spears helped the United States survive Y2K with her bubble gum pop and glittery fashion back in 2000. When her second album Oops! . . . I Did It Again came out on May 16, 2000, she was at the top of her game and I completely adored the former The Mickey Mouse Club member (MMC 4 Lyfe!). As I was maturing, so was Spears: Oops! . . . I Did It Again was a baby bit less cheesy than . . . Baby One More Time and she was starting to reveal more of the Britney that we know today.

Ever since she hit the music scene, Spears received backlash from the media for her at-times promiscuous clothing choices. But her sports bras in the music video for ". . . Baby One More Time" were tame compared to her sexy beach look from her sophomore album's song "Don't Let Me Be The Last To Know." Spears was using Oops! . . . I Did It Again to help launch her into her (bizarre) adulthood — and define her sense of fashion through her music video outfits.

Four of the songs off of Oops! . . . I Did It Again were made into music videos and her outfits in all four music videos showed that Spears could be the girl next door or a sex symbol at the drop off a hat. Not long after Oops! came out, she stayed true to the line "I'm not that innocent" from the title track song and my judgmental, fairly innocent early teen self was temporarily disheartened by the Princess of Pop. Although I wanted to still dance like her in the music video for "I'm A Slave 4 U" (from her third album), I realized I may never see Spears in a full shirt again.

But the girl (not yet a woman) taught me about sexuality during that Oops! . . . I Did It Again phase — not just through her lyrics, but through her clothing choices. It was OK to be the wide-eyed, fun-loving teenager, but then still have people desire you for your great body and sexy dance moves. That range of innocence to full-blown sex object has pretty much defined Spears's career, so with Oops! . . . I Did It Again turning 15, it's time to rank the outfits in the four videos she made: — "Oops! . . . I Did It Again," "Stronger," "Don't Let Me Be The Last To Know," and "Lucky" — from worst to best.

"Stronger" Black Witch Outfit

Any Spears fan loved the callback she made to ". . . Baby One More Time" in the lyrics for "Stonger." Her loneliness ain't killing her no more! Unforunately, I did not love her first outfit in the "Stronger" music video. With a black choker, lace, a mysterious flower on her chest, a witch skirt, and crimped (crimped!) hair, this outfit was already outdated in 2000. (Although, I am loving the acceptable crimped hair in her new music video "Pretty Girls.")

"Lucky" Intro Pink Shirt

I totally blame this shirt on the year 2000. Pink camouflage is never OK (nothing ever in the world is naturally that pink that you'd need to blend into!), but my biggest issue is with the shimmery lace-ups on the sides and front. But bonus points for those huge-ass hoop earrings!

"Lucky" Narrator Red Shirt

Although Spears looks lovely (just like Lucky herself), I ranked this outfit so low because of the weird sequined strip going across the top of her shirt. Based on interviews from this time period [ANNA CAN WE LINK TO MY INTERVIEW ARTICLE HERE? :)], this was definitely a trademark style that Spears was trying to make happen and I'm glad it didn't really catch on.

"Oops! . . . I Did It Again" Black Mini

I realize that leather (or perhaps pleather?) was all over the "Oops! . . . I Did It Again" since the music video took place on Mars (everyone knows that martians love pleather), but her black, leather miniskirt just didn't seem dramatic enough for the scene where she receives Titanic's "Heart of the Ocean" necklace.

"Lucky" Pink Dress & . . . Jeans??

Overseeing Lucky from the sky, Spears peered down at her alter ego — and threw a lot of glitter. The pink dress of her benevolent star outfit is kind of striking, but then you see she's wearing jeans (???) underneath. I mean, she couldn't be sitting straddle style on a star like that if she didn't have pants underneath (or could she??), but the gown on its own would have been classier. Perhaps the pink dress represents the glamour of Lucky, while the pants underneath represent the down-to-earth Britney. (Getting deep over here!)

"Stronger" Black Two Piece Outfit

Spears makes this college dance team outfit look good, but the ruffled glitter on the bottom of the pants? Too much. Yet I'm willing to accept it all for her badass dance moves with that chair.

"Lucky" Black Two Piece Outfit

Maybe it's the hair, the earrings, or the flawlessly toned stomach, but I somehow find this two piece black outfit from "Lucky" acceptable. These type of outfits make sense from a dance perspective, so I can see why Spears liked them . . . even if she doesn't dance in this video . . . hmmm. Of course, no one should dare to wear that turtleneck, keyhole, crop top but Britney.

"Oops! . . . I Did It Again" White Crop Top

I'm just as shocked as you are that I have chosen to place Spears's white turtleneck half top so high on this list, but doesn't she look so pretty and ethereal? This was the Spears I wanted to be in 2000 — and the epic hair extensions don't hurt either.

"Lucky" Red Carpet Dress

Lucky earned an acting award in the music video "Lucky" (something I don't think Spears will ever receive — sorry, Brit!) and she wore a silver, body-hugging gown. The world keeps spinning and she keeps on winning, so she needed something classy — yet age appropriate — and this dress nailed it. Plus, it showed that her body was rocking even when it was mostly covered up.

"Don't Let Me Be The Last To Know" Bikini Top & Jean Shorts

No costume changes were necessary in Spears's sexy music video for "Don't Let Me Be The Last To Know." Spears was pure perfection in her little off-white crotched bikini top, ripped jean shorts, hoop earrings, and mini cross (you can still be sexy even if you love Jesus!). Points were only deducted for the two-toned back pockets of the shorts. This music video outfit might have been simplistic, but by showing more skin, she officially shed her pure image.

"Lucky" Glam Bathrobe

The best outfit of the "Lucky" music video was Lucky's classic screen siren bathrobe. Look at the hair! The necklace! The beauty mark! She looks so glamorous, I can barely stand it!

"Oops! . . . I Did It Again" Red Catsuit

I'm a serious sucker for jumpsuits, but even if you aren't a fan of the one-piece clothing item, you can't deny that this Britney look was by far the most iconic from the Oops! era. Honestly, behind ". . . Baby One More Time" and "I'm A Slave 4 U" this is one of her most notable looks. And damnnn, girl looked good. The red latex catsuit was even the 18-year-old's (yes! 18! She was born in Dec. 1981!) idea. Sure the black clunky jazz sneakers aren't great, but I'm going to point out those amazing hair extensions again and the fact that I don't know anyone else who could pull this off. Fifteen years later, we should still all be hailing Britney Spears — the Princess of Pop!

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