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

[LostInAnImage]

Let me preface this by stating this is not yet another superfluous thread with the intention of bashing Britney’s appearance. Rather, it’s simply to have some nostalgic fun by posting some examples of the worst, tackiest, or just plain weird fashion statements that were stylish two decades ago. Makeup trends indicative of that time period are also welcome. I’ll start!

1998:

1999:

2000:

2001:

2002:

[BRSM_jl]

I love the 2000's so much 

[LostInAnImage]

Here’s an article about 2000’s fashion; Brit and Xtina are mentioned multiple times. 

https://www.bustle.com/articles/168084-13-trends-younger-millennials-loved-that-older-millennials-dont-get-photos

[fnfurter]

4 minutes ago, LostInAnImage said:

Here’s an article about 2000’s fashion; Brit and Xtina are mentioned multiple times. 

https://www.bustle.com/articles/168084-13-trends-younger-millennials-loved-that-older-millennials-dont-get-photos

That article makes me laugh, because Britney IS an older millennial. Like.... clearly she got it, so that destroys that entire article right out of the gate.

Anyway, on topic--

[BOBIBCFBG]

fashion was so all over the place in 2000 lol

[LostInAnImage]

42 minutes ago, BOBIBCFBG said:

fashion was so all over the place in 2000 lol

That’s an understatement. I mean, how in the hell can these two looks not only be from the same era, but the same evening?

[Martini]

16 minutes ago, fucknfurter said:

That article makes me laugh, because Britney IS an older millennial. Like.... clearly she got it, so that destroys that entire article right out of the gate.

Anyway, on topic--

Lol Rachel Zoe said she styled her here too 

[LostInAnImage]

6 minutes ago, Martini said:

Lol Rachel Zoe said she styled her here too 

 I can’t believe someone was actually paid to come up with this ensemble.

Since it was so early in her career and she brought her mom to the red carpet, I always figured she had picked it out on her own and done her own makeup/hair with her mom’s assistance. 

[LostInAnImage]

45 minutes ago, BRSM_jl said:

I love the 2000's so much 

Truthfully, I would take back the white eyeshadow, body glitter, platform shoes, butterfly clips and pleather pants without hesitation if it meant current pop songs/performances were commensurate with the 2000’s as well. 

[LostInAnImage]

My first picks for most questionable hair/makeup trends from same time period:

(Light pastel purple, blue/green and/or excessive white eyeshadow and glossy, dark brown (oft overlined) lipstick; unfortunately, Brit seemingly combined all of the above trends for these particular occasions):

Other glossy, dark brown lipstick offenders:

[LostInAnImage]

And here’s some other excessive chalk white/bright blue-green and/or pastel purple-pink eyeshadow offenders, but sans brown lipstick:

Britney's eyeshadow extravaganza never became even remotely as bad as any of the above though:

(Okay, the last one is a bit much).

[redacted statement]

the 00s were such a mess fashion-wise and I love it!  

[LostInAnImage]

2 hours ago, BRSM_jl said:

I love the 2000's so much 

 

2 hours ago, fucknfurter said:

That article makes me laugh, because Britney IS an older millennial. Like.... clearly she got it, so that destroys that entire article right out of the gate.

Anyway, on topic--

 

2 hours ago, BOBIBCFBG said:

fashion was so all over the place in 2000 lol

 

2 hours ago, Martini said:

Lol Rachel Zoe said she styled her here too 

 

24 minutes ago, I Always Sing Live said:

the 00s were such a mess fashion-wise and I love it!  

So, what's the verdict on crimped hair? Wouldn’t be a proper 90s/00s thread if I left that craze out. Now, I realize the instinctual reaction to my question is generally ”hell no,” but it actually looked cute sometimes (and, of course, atrocious during others). For fairness, I’ll add pics of (what I believe are) representative of both. Thoughts? (So as not to influence you in this very important debate, I’ll allow you to personally decide which pictures fall under Crimp Cons and which are Crimp Pros).

[circusbritney]

How has this not been posted yet

[LostInAnImage]

9 minutes ago, circusbritney said:

How has this not been posted yet

It was initially in my OP, but her hair and makeup were so deceptively gorgeous that I changed my mind about including it.

But you’re right, based on the outfit (and hat) alone, it definitely belongs here.

[CristMont]

QUEEN OF 00's tbh 

[fnfurter]

Crimped hair discussion: first Brinni is terrible, second is good, first Xtina is too much but not terri-bad, second is okay, I actually think both of Tyras look mehhh but I'm gonna say the really bad one is the second, and then the first is okay and the second is wtf of Hilary.

19 minutes ago, circusbritney said:

How has this not been posted yet

I kind of don't count it because she intentionally wore that to be put on the Worst Dressed List, to annoy the critic who kept putting her on it, anyway.

[LostInAnImage]

4 minutes ago, fucknfurter said:

I kind of don't count it because she intentionally wore that to be put on the Worst Dressed List, to annoy the critic who kept putting her on it, anyway.

I forgot about that! It kind of backfired on her though, since she won Album of the Year and then had to go accept the night’s biggest award dressed like that. At least she took her pimp hat off before going on stage though. 

[Mona Lisa 2.0]

2003 

2007

 

[LostInAnImage]

2 minutes ago, Mona Lisa 2.0 said:

2003 

 

 

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.

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