Oh, baby, baby, we sure did want to look like Britney Spears in the late 1999s to early 2000s. We wanted every single outfit from her classic “Baby One More Time” sexy schoolgirl look to her wardrobe crammed full of belly-baring crop tops, save for her double denim disaster with Justin Timberlake at the 2001 American Music Awards. Even back then we knew that was an utter mistake. While Britney’s retro pigtails and red leather catsuits may drive us crazy now, we totally loved them then.
Put on your old “Baby One More Time” album and check out 12 WTF Britney Spears looks we were obsessed with:
That shiny green crop top was pretty great, but this cute waitress outfit was what fascinated many of us. How do we get our pigtails to look that cute? Can you really buy pink glasses? Plus, we wanted to be like Melissa Joan Hart in this video, and be Britney’s BFF.
Okay, so we didn’t all want to run out and buy red long-sleeved leather catsuits, but we did love the look. What we did really, really want to copy was that frosty smokey eye and that clear lip gloss. Oh, the number of Bonne Bell glosses we looked at to find the best one.
It’s confirmed that our crop top obsession can be attributed to Britney Spears, but did she also start the embellished belts and arm cuff love affair? Remember the pleasant jingling sound you’d make when you walked, just like a cat with a bell on its collar?
If you didn’t have to wear a uniform to school, you wanted to just so you could wear those fluffy hair elastics. And if you had to wear a uniform, you complained endlessly how it was against dress code to wear them. You made up for it when you wore the proper look on the weekend, complete with the furry hair accessories.
(Via Frank Micelotta/Getty Images)
The snake definitely counts as an accessory for this look. This VMAs performance outfit is iconic. It showed us that cut-offs can never be too short, or over-embellished, and that you can fashion a sexy top out of a scarf.
Click the next page to see more retro Britney Spears looks we were obsessed with.
Thank you Britney for making us desperately search for short-sleeved cardigans in the Juniors department, and for making it a style rule that white tank tops and chunky platform sandals had to be worn with everything.
Are those fringed pants? We wished we knew how to sew so we could have embellished our pants, since we knew we could never find those amazing trousers in the store. This video was also responsible for numerous kitchen chair accidents and injured ankles.
(Via Vince Bucci/Getty Images)
We can thank Crossroads for fueling our obsession with bucket hats with pigtails, but the premiere gave us this iconic look. You loved your paperboy caps but this made us want to add a pink leather one to our hat collections. And who didn’t go through a phase of wearing their nightgown over jeans?
I don’t know anyone who went as far as wearing their thong over their jeans, other than for a possible “Slave 4 U” Halloween costume, but if you did, I want to hear about it. Many of us were intrigued enough to try it in the privacy of our own bedrooms to see if it could work.
What a great video for athletic looks. Even those of us who hated gym class wanted to wear tearaway pants and a sporty crop top. Mel C‘s look was too sporty, but Britney with her, erm, high half pigtails was just right.
Some of us may not have liked Brit’s slower songs, but we did like many of her fashion looks from her “Lucky” video. The glamorous Lucky look is Barbie-tastic, but the casual red top with lace-up white jeans is the one we copied. Why have an easy zipper fly, when you can struggle to lace up your jeans like your shoes?
12. Baby One More Time Tour, 1999
(Via Brenda Chase/Getty Images)
Another girly sporty look we fell for. Everyone loved an early Millennium tube top, but this shiny pink one deserves to go in a museum somewhere. Add in pigtails and some body glitter and this was the ideal going out ensemble.