(Closed) Your generation’s questionable fashions

posted 9 years ago in The Lounge
Post # 3
8736 posts
Bumble Beekeeper
  • Wedding: September 2011

@ohheavenlyday: I was in high school around the same time you were. 1998-2002.

The one I remember was rocking this hairstyle with a visor:

I thought I looked like sporty spice.

Post # 4
1831 posts
Buzzing bee
  • Wedding: December 2010

I second the graphic tees and faded jeans. Faded jeans do no one justice after a while. I was never into the boots… but I was into the really low cut shirts. I have average size breasts and never really thought about it until entering a professional work environment. Anything too low makes me really uncomfortable now! Even when it’s on other women I want to cover them up 🙁 Maybe it’s my maternal instinct?

Post # 5
2088 posts
Buzzing bee

Unfortunately my generation (high school 2005-2009) was big on the on-purpose-whale-tail trend.  *shudder* I participated in this once, when I was 15 and at a dance. Never again:

-crocs (thankfully I never bought into this trend)

-crocs with socks

-basketball shorts with graphic tees and flip flops 

Post # 6
5493 posts
Bee Keeper
  • Wedding: August 2011

I was in high school 1997-2001 and I think every picture of me has my middrift showing.  Other chocies that now make me shake my head:

colore sunglasses

glitter makeup

fake cornrows held in place with multicolor butterfly clips, (anyone know what I’m talking about)

those tiny short ruffle skirts that are really only beach appropriate


Post # 8
1643 posts
Bumble bee

Oh the jean skirt and platform flip-flops!! I had those!! AAAGHHH! And I was in high school from ’02-’06! The thick heels, the glitter eyeshadow. God, no!!

I would just like to point out, however, that once in 7th grade I wore some (low) heels with jeans, and a girl made fun of me. Guess what she was wearing today? THAT’S RIGHT.

Post # 9
1759 posts
Buzzing bee

I’m a 1998-2002 high schooler, too. I loved flare jeans. I still do! Actually, I had a pair of bell bottoms that I really loved because they balanced my big butt. I can’t wait for them to come back. I have big calves so I have trouble with just boot cut pants, lol. I didn’t really follow any other trends. I was super uncool. Now that I think about it, I really don’t dress that differently now–yikes.

Post # 10
177 posts
Blushing bee
  • Wedding: November 2011

I grew up in the 90s and 00s



— neon

–tracksuit bottoms matched with just about anything (blame sporty spice)

–name headbands, necklaces you name it (not meant t be a joke but… ha)

–platform shoes

— trainers with everything



— those weird shaped t shirts that were kind of triangular shaped at the bottom?

— pedal pushers

— bindis

— “hippy” look tops and bandanas

— millitary combats with loads of stringy things hanging off (about 2003)

— peplum skirts


The 80s gets a bad rep but the late 90s and early 2000s were horrific!


Post # 12
2088 posts
Buzzing bee

@ohheavenlyday:  That triangle-shaped piece of fabric on the back of a thong, it resembles a whale’s tail. A la the girl on the left

Post # 13
1759 posts
Buzzing bee

@beebee89: Oh man, I totally remember those triangle bandanna shirt things. Hilarious!

Post # 14
1746 posts
Bumble bee
  • Wedding: May 2012

Y-necklaces circa when they were hot on Friends. Can’t look at the letter “Y” now without cringing…

What was worse than faded denim was RIPPED denim. Like, shredded all over your legs and knees . Diaster.


Post # 16
633 posts
Busy bee
  • Wedding: April 2011

I went to high school (2003-2007). I took part in the 2″ zipper Dorina jeans that looked like they were painted on. The “whale tail” was also popular at dances. I also constantly got in trouble at school for showing my mid-drift in baby tees with a long dangling belly button ring. Yes, I was that bubble gum princess. Thankfully I was also student body president and a goody-two-shoes so I didn’t look overly trashy, just like a little tart haha.

Britney Spears was my fashion Idol. Thank god I have more sense now…

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