12 Heinous Celebrity Fedoras to Remind You That the 2000s Weren’t THAT Great

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Jan 26, 2018 2:00 pm·

By Mary Grace Garis

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Known universally as the most abominable of all hats, no self-respecting celebrity would be caught in a fedora today. But back in the 2000s, the horrendous piece of headwear was a favorite of all your favorite (and least favorite) stars. It feels like Justin Timberlake had one for every day of the week.

So in case you were having any nostalgic warm fuzzies about the era, here are a handful of unfortunate fedora moments from the turn-of-the-millenium to set you straight.

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Christina Aguilera

Yikes. Opting for her best Oompa-Loompa look, Xtina decided to match her hot pink lipstick to her hot pink fedora. Also, Boy George was at this event and he still looked just a little bit more understated.

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Gwen Stefani

Every legit insane element of this outfit is pure early 2000s Gwen. The bikini top over the fishnets, the men's tie over that, those baggy plaid pants, it was a mess and yet we were sort of OK with it. But that fedora? Unacceptable.

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Kim Kardashian

Vintage Kim K puts a questionable straw twist on the classic fedora. Also, we have no idea what's happening below the neck either. Shorteralls?

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Britney Spears

Witness here that Brit-Brit is making our exact horror-face that we made at this fedora.

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Lindsay Lohan

And witness LiLo, in happier times, going boating in what appears to be a brown (ew) horseshoe print fedora. This definitely wasn't her worst mistake of the 2000s, but it's up there.

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Justin Timberlake

Oh god. Justin Timberlake won't let the fedora die, even deep into, like 2013. He's obsessed, and we don't know why that's not treated as a glaring red flag. But this is a particular fur rendition from 2002 is really something else.

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But also this masterpiece takes the cake.

It should be framed, and that's that.

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Kevin Federline

Not to be upstaged by Britney's ex, K-Fed epitomized the fedora. Also, Brit is already regretting her marriage to this guy.

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Nicole Richie

A tasteful pink-velvet-trimmed fedora, accessorized with some skunky hair extensions.

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Paris Hilton

Paris' fedora almost blends into the background, but then you see it: straw and with a leather trim? Nope.

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Kelly Rowland

Kelly literally looks like she stepped out of the 1920s with those pinstripes, we're shocked she didn't match it with a zoot suit.

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Nick Cannon

If you're invited to P. Diddy's white party and are encouraged to look your absolute best, there's only one thing that can top off your immaculate ensemble: A fedora.

Sigh.

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