The 8 Photos Britney Spears Doesn’t Want You To See!

Britney Spears made history after donning a tied up schoolgirl outfit in her first video for her hit song Baby One More Time. Since then, she’s graced every red carpet from the Billboard Music Awards to the Grammys. While the pop princess has scored many awards for her music, she won’t be winning any best dressed awards anytime soon.

We love you, Brit. But we hate these outfits.

Here are Britney Spears’ 8 most disastrous red carpet fashion moments. File these under “what the hell was I thinking”…

8. Pre-Grammy Party, 2002

Britney Spears arrives at the 2002 pre-Grammy party donning an unflattering, two-toned, off-the-shoulder dress that looks like it could be a hand-me-down from Courtney Love circa 1995.

Britney Spears Worst Dressed
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7. NSync Launch Party, 2001

Just because you have the body to wear a midriff-bearing top doesn’t mean it’s a good idea. As though the top isn’t hideous enough, everyone’s favorite Southern belle paired it with a pair of prune-colored bell bottom jeans and a silver choker necklace. Nice.

Britney Spears Worst Dressed
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6. Teen Choice Awards, 1999

If you’re looking for an attention-grabbing ensemble that will set you apart from everyone else, ask Britney to borrow this outfit from the 1999 Teen Choice Awards. Sure, it was almost a decade and a half ago but, rest assured, even in the heat of the atrocious 90’s fashion scene, disco-sequined pants were never in style.

Britney Spears Worst Dressed
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5. American Music Awards, 2003

You’d think by 2003 Brit would have graced enough red carpets to know what’s acceptable and what’s not. Unfortunately, the multi-million dollar singer still showed up to the American Music Awards wearing an outfit that looks like an 80’s figure skating uniform that lost a fight with a paper shredder.

Britney Spears Worst Dressed
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4. The Four Feathers Premiere, 2002

I don’t care if you’re the most successful music icon of the decade, there’s absolutely no excuse for wearing tie-up pinstriped pants and a top hat anywhere, let alone a red carpet event. Come on, Brit.

Britney Spears Worst Dressed 5
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3. Crossroads Premiere, 2002

Anyone who says ‘there’s no such thing as too much pink’ obviously hasn’t seen Britney Spears circa February of 2002. The starlet donned a baby pink hat with a matching baby doll dress and knee-high, pointy-toed boots. Oh, and to top it all off, she threw on a pair of rolled-up denim capris – because, you know, without them the outfit might look trashy.

Britney Spears Worst Dressed 8
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2. Teen Choice Awards, 2001

Where do you even begin with an outfit like this? Basically, Brit’s stylist paired a baby pink men’s dress shirt with a button-up denim skirt and denim bra. Here’s hoping she fired her stylist later that night.

Britney Spears Worst Dressed 3
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1. Billboard Music Awards, 2000

Each piece of the outfit Britney chose to wear to the 2000 Billboard Music Awards is hideous enough to land the number one spot on this list. Combine them all into one ensemble and you have the most disastrous outfit to ever grace the body of Miss Britney Spears. From the ridiculous hat to the mauve tights and red velvet boots, this outfit has disaster written all over it. Sorry, Brit!

Britney Spears Worst Dressed 1

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