58 Times Britney Spears's Wardrobe Was the Stuff Your '90s Dreams Were Made Of

And, OK, sometimes the stuff of nightmares too.

I mean, just look at it! (And then throw it all into a bonfire.)

Here’s Britney at the very first Teen Choice Awards. And there are big sequin paillettes on her pants.

Britney’s early commitment to semi-formal lingerie was impressive.

There is just so much going on here, but perhaps best of all is the frosted eye shadow? OK, or the maribou feather hemline on Brit’s silk pants. I just can’t decide!

OMG, look, more dramatic eye shadow, circa the 1999 MTV Video Music Awards. Also, more maribou feathers; Britney has always styled herself like a fledgling Britney impersonator, when you stop to think about it.

TBQH, it’s like Britney and Melissa Joan Hart (remember, Brit and Melissa both starred in the “(You Drive Me) Crazy” music video, alongside ’90s bae Adrian Grenier) had a competition to see who could look frumpier. They both win!

Belly chains! Skirts over pants! So much going on here!

OK, also a helluva lot going on here. I mean, when were your fave heels ever this square-cut, thanks very much?!

This is just a cute photo.

This, meanwhile, is an insane photo. You’ve got to love it — Britney’s commitment to illogical (bad) headwear has long been impressive, after all.

This is iconic, for example. And not just for the hat. It’s Britney at the 2000 Billboard Music Awards, and never has anyone ever dressed better for the red carpet (other than the time Björk wore a swan, obviously).

Look, she’s even serving hats by osmosis! Any excuse for a good J.Lo photo; this is from the 2001 MTV Video Music Awards, but it could just as easily be from this year’s, really.

Meanwhile, this isn’t technically a hat, but let’s count it? Britney loves punk, after all. “Golf punk” specifically though.


Look, more Justin! This chunky knit turtleneck was a maj menswear moment, and Britney’s choker is cute too. She also has crimped hair, FYI. Always setting trends.

“Control freak.”

IDK about this though, IDK about this one bit.

Looking like they both just stepped out of the Buffy the Vampire Slayer wardrobe department (as Buffy circa season four, and Angel circa season one) here’s Justin in a way glam sheer shirt and Britney in more lingerie. You’ve got to love them. And miss them.

You might think the most important thing here is that shredded jersey batwing sleeve thing happening. But you’re wrong. It’s actually the fact that Brit’s pants aren’t quite zippered up all the way. That was OK in the early 2000s, I think?

Literally just wearing an oversize men’s V-neck sweater and looking perfect. Yes.

#SURFBORT some more.

If you didn’t own a chunky faux-fur lined cardigan, were you even alive in 2005?

Just look at all these fabulous butterflies.

Britney loves a good biker bar newsboy cap.

I wasn’t joking about the newsboy caps. But let’s also quickly mention (1) the thigh-high boots, (2) the dress over jeans and (3) JUSTIN TIMBERLAKE’S SHINY PANTS, because they are disgusting and yet … so attractive? There’s more noodle-haired Timberlake to come, don’t you worry.

It’s a TRL flashback, my gosh! And also, legwarmers!

Let’s not even pretend Britney knows what’s going on here.

This is basically a turtlenecked sack, but Britney’s smiling with her eyes, so who’s going to complain?!

You’ve been waiting for the velour, haven’t you?! Here it is, in all its Juicy Couture glory. Britney Spears owned this trend.

Oh no, Britney is unraveling a little bit ? ?

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