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

[LostInAnImage]

10 minutes ago, I'mNotTheAverageLady said:

That's so cute of you the I want candy look is a timeless classic from Britney (Barbie) era. The most 2001 thing I can recall anytime

Yeah I love this outfit too, so eccentric

Which outfits landed her on the "worst dressed" list? (This, the Grammy 2000 one that I know about)

Oh man, I don’t recall them all, but I do remember her being an extremely regular addition on those lists. One that notably comes to memory includes the double denim with JT, but she was honestly on the top 10 of those lists nearly every year, and was #1 in 2006:

Britney has topped Mr. Blackwell's 46th annual “Worst Dressed” list for wearing clothes that he said made her look like an “over-the-hill Lolita.”

“When it comes to Couture Chaos, this Tacky Terror should take a bow — looks like an over-the-hill Lolita,” Mr. Blackwell said in a statement released Tuesday.

[rawbrit]

1 hour ago, LostInAnImage said:

Haha, that second outfit was during a Crossroads premiere in Amsterdam, so perhaps she was just partaking in the legal weed smoking within their “coffee shops” beforehand. It would certainly explain her a) wearing socks with heels, b) the carton of popcorn attached to her hand all night, and c) the goofy, carefree grin she maintained for the majority of the event.

 

(Not judging at all BTW, I’d most likely do the exact same given her insane promo schedule at the time).

LOVE the necklace here btw

[BritneysBitch82]

52 minutes ago, I'mNotTheAverageLady said:

Ohh your theory perfectly explains it

I even say I like this outfit despite its goofiness (or because of it). It's really boho chic like a lot of her early 2000s outfits but it's more over the top than the others and I personally think it's stylish and cute (that's my weird taste here)

The thing I love most about 2000s Brit's fashion is the asymmetrical crop tops

 

 

There are a lot more and I so want to post them all but I don't have time to search all

 

My fave bubblegum pop look

Love these lewks. Esp the Stronger Amas look

[paula24bs]

Ok in general I really love britney's 2000s fashion, but there are some ugly/cringe outfits for me

 

 

I dont' know about the skirt on the next one

 

This seems like a grandma dress with weird shoes

 

In general this is awesome, but those leg warmers make it weird. Remove it and it's a perfect outfit

 

WTF is this?

 

I always hated this one

 

Not that bad in general, but it was not appropriate for the ocasion (too casual for me)

 

Love the skirt and boots, but hate that shirt!!!

 

 

and final one (I've never seen this one but it's terrible)

 

 

[LostInAnImage]

9 hours ago, paula24bs said:

Ok in general I really love britney's 2000s fashion, but there are some ugly/cringe outfits for me

 

 

 

This is even better once you add in A) the oversized leather jacket:

And B) this...headless woman wearing a hard hat? 

[paula24bs]

Just now, LostInAnImage said:

This is even better once you add in A) the oversized leather jacket:

And this...headless woman wearing a hard hat? 

omg I've never seen the jacket...that's terrible ahhahah

[SonOfSun]

For example this look is very 2018 :

(by the way if anyone knows where we can find the video please post it)

 

[LostInAnImage]

8 minutes ago, SonOfSun said:

For example this look is very 2018 :

(by the way if anyone knows where we can find the video please post it)

 

I’ve actually never seen these gifs before! She looks so cute! 

[fnfurter]

18 minutes ago, SonOfSun said:

(by the way if anyone knows where we can find the video please post it)

I could only find this one, but it's MTV's Spring Break 1999.

 

[fnfurter]

I can't edit it, but that's not even the segment that is. I don't know where they found that part.

[I'mNotTheAverageLady]

1 hour ago, paula24bs said:

I always hated this one

 

I love this one so much, she was stunning here!! I think it's stylish

And this is one of the looks that are totally relevant now, in 2018. I can see some fast fashion brand selling this dress and the big hoop earrings and the thigh high boots are also a thing

[BritneysBitch82]

9 minutes ago, I'mNotTheAverageLady said:

I love this one so much, she was stunning here!! I think it's stylish

And this is one of the looks that are totally relevant now, in 2018. I can see some fast fashion brand selling this dress and the big hoop earrings and the thigh high boots are also a thing

This look is totally in

[portrait]

3 hours ago, LostInAnImage said:

I’m not a fan of hers by any means, but she truly can look beautiful (particularly prior to all the unnecessary plastic surgery procedures; her natural exotic look was stunning). I just don’t understand how someone can always look like they’ve spent hours in hair and makeup, simply to go to dinner or even walk around town for a minute or two. And this is coming from someone who adores their consistently (fully stocked) vanity!

But frankly, the entirety of her lifestyle seems both exhausting and pointless, and her legions of cognitively immutable troglodytes cause me great concern for the future.

she can look beautiful and radiant, indeed... but the look you posted is just vulgar (for my taste) and screams desperation. and like another user wrote , it's her lifestyle and job... lol 

and this may sound naive, but I wonder who exactly decides what is a trend again.. but okay this is again another topic, I'm drifting away 

[I'mNotTheAverageLady]

Now that I invested time on this topic, I can't stop myself looking for new pics I love fashion and love the early 2000s, so that's a perfect topic for me (except I don't find a lot of fails)

These are really nice

 

This makeup - oh my godness so gorgeous

 

A really hot one

 

At her book's, Stages release party - suc a barbie look!

 

 simply beautiful

 

 

 

This denim jumpsuit is high fashion lol

 

This top is goalsss

I'm nostalgic as hell right now

[JeNny_C]

I grew up during this time and even though some of it's tacky, I always loved it and thought Britney was so cool because of what she wore.  I know others won't agree but I think it was a fun time and wouldn't mind it if some of these trends came back.  Just sayin... 

[LostInAnImage]

1 hour ago, JeNny_C said:

I grew up during this time and even though some of it's tacky, I always loved it and thought Britney was so cool because of what she wore.  I know others won't agree but I think it was a fun time and wouldn't mind it if some of these trends came back.  Just sayin... 

No I totally agree, I was obsessed with her style! I even got my bellybutton pierced because of her, haha. 

[naturalplayboy]

12 hours ago, STJ said:

i don't understand the glasses or the hairstyle...

pimpney

 

 

The glasses are making a comeback. They are on trend this season.

[fnfurter]

6 hours ago, I'mNotTheAverageLady said:

For the record, I generally agree with everything you said, but this one gets me because the patterns don't match: and while that's fine (she looks stunning), back then I wore a pair of low-cut, patched jeans (y'all know the ones, there's probably a shot of Britney in a pair from the 2000s somewhere) with this one particular colorful top and was told by my fellow classmates that they didn't match a lot. (Yes, they freaking did. Also, who cared if Britney was getting away with mixing these two.)

[rawbrit]

9 hours ago, LostInAnImage said:

 

 

 

[LostInAnImage]

35 minutes ago, naturalplayboy said:

The glasses are making a comeback. They are on trend this season.

I believe you, but I wish you were lying. I mean, how can anyone think these:

Look better than these?