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Late 90s-Early 2000s: Most Questionable Fashion Choices


LostInAnImage

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23 hours ago, LostInAnImage said:

I know it’s so tacky, but I’ve always loved this look for some inexplicable reason. I think it’s so bad that it’s actually good. Primarily though, I think I like it because it’s so cheeky, making fun of pop culture and tabloids. It’s like the fashion equivalent of “Piece of Me” (the song). You could tell she was having a lot of fun with it.

britney-spears-arrives-wearing-a-fedora-

Also, I like this one super stoic shot where it looks like she's posing for a mugshot or the DMV or something: 

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I used to like it too but then I noticed those awful tights with the high heels and that ridiculous bow tie (and the hat idk why she loves hats so much) :eeek:

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22 hours ago, Delicious Pork Chops said:

This was a look tho. It would just need to be slimmer fitting to fit today's standards. 

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You’re right it was definitely a thing, I’ve just personally always hated overalls. I always cringe during the first few seasons of Friends when Jennifer Aniston wears them, haha. Her style became great during later seasons, though, 

Dont-Even-Get-Us-Started-About-How-Cute-

Rachel-Friends-Shortalls.jpg

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5 minutes ago, Delicious Pork Chops said:

overalls are some of the things people wear nowadays

Yeah, I was unaware but when looking up those pics of Jennifer Aniston, I stumbled upon several articles stating they are back in style. Just not my personal preference, I suppose! :)

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1 hour ago, Britneylandia said:

Britney was a huge influence back then. 

We know Britney has a horrible taste for clothes.

The 2000’s were horrible fashion wise.

Britney influenced the 2000’s.

EVERYTHING MAKES SENSE NOW.

She did make some great contributions to the zeitgeist though, even in terms of fashion. I mean, it wasn’t all bad.

Like, the crop top, low rise jeans and bellybutton ring was her signature look, and it consequently became ubiquitous among popstars. And I honestly still love that overall look, even if it’s considered dated. To me it has a casual, almost timeless *** appeal to it. All the fashionistas and “it girls” just try so damn hard nowadays. I liked how Britney’s free spirit and tomboy streak came through even in her style. 

IMO, this first look will always be sexier than the second one:

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Kim-Kardashian-Yeezy-PVC-Wedge-Mules.jpg

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2 hours ago, Stannedforever said:

denim-style-icons-justin-timberlake-and-

I still think the denim dress is beautiful :janet: could have had more details on it tho. Justin's suit was fugly:chershade:

Well I don’t know about the dress in and of itself, but she was so damn stunning she actually made it work. I loved her diamond choker though. 

And yeah, JT looks like some farm boy auditioning for American Idol, but apparently Britney and her stylist made him that jacket as a joke anyway, not expecting him to actually wear it. However, I think the most egregious fashion offense is that damn denim cowboy hat. Just...no.

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