back to top

24 Early Britney Outfits You Can't Unsee

But, like, in the best way possible because shiny drawstring pants FTW.

Posted on

1. This is Britney's costume from the very early days when she was touring "Baby One More Time" on the Vaudeville circuit. They didn't have much. But they had platform sneakers.

2. Is there a word for drawstring denim cargo pants? Cardraw jeans?

No further comment on the fuzzy blue coat.

No further comment on the fuzzy blue coat.

3. This girl really had a thing for drawstring pants.

4. The symbolism in this photo is blowing my mind.


5. Nothing like a see-through top and blindingly shiny pants to say, "Superstar."

6. Part of me wants to believe the wardrobe department received the wrong size in this top and just hoped she wouldn't notice.

7. All a girl needed in 1999 was a crocheted tank, cargo pants, and work boots to be the next American sweetheart.

8. Remember these tattoo/dragon/Chinese graphic shirts? (May they rest in peace and never see the light of day again.)


9. Yes, children, there was a point at which wearing pigtails was a socially acceptable form of coiffure.

10. This sweater=barf.

11. Funny how the whole camouflage trend made you stick out like a sore thumb.

12. Ahh! Remember that summer when everyone wore Roxy board shorts?


13. The tire was Britney's idea to lend a bit of toughness to this snowboarder-superhero look.

14. This is the kind of outfit your mother would never understand. Why wear a puffy vest if you're going to wear nothing underneath it?

15. Never knew Britney was such a Lisa Frank fan.

16. Ahh! Striped corduroy pants! I banish thee!


17. It's like a fringe curtain for your belly.

18. The hard thing to digest about this outfit is probably actually wore something almost exactly like it.

19. Hobo pants in da house!

20. This is what you wear when you've challenged Stevie Nicks to a fist fight.


21. These two things do. not. match. Stop trying to make it happen.

22. Oh look, it's a hologram tee from DEB.

23. I feel this is the type of outfit that if you're not careful, it could end up permanently attached to your body.

24. If this was a pic from Britney's role as Titania in her high school play, that'd be amazing. But because I do not know why she is a fairy, this outfit is simply puzzling.