Twentysomethings Fess Up To Their Most Embarrassing Teenage Fashion Moments

We all have those photos that we look back on and wonder how we EVER thought we looked good. From popped collars to silver eyeshadow, we asked seven real chicks to fess up to their biggest teenage fashion fails. Trust us, you’re going to want to read these…

Burnt Biscuit

“Once when I was in high school, I went in the tanning bed for way too long and became a lobster to say the least. I then proceeded to wear a red shirt (that was 2 sizes too small so my burnt belly showed) with a denim skort that had a distressed hemline and a 2-inch thick white headband. Someone recently dug up a photo of this outfit, and that’s why my memory is so vivid!” – Jessica P.

Glitter Feign

“When I was around 13 and in middle school, I loved silver eyeshadow (not just a little, I caked it on!) and blue eyeliner. I also had this silver glitter belt I wore way too often, along with every other middle schooler. It’s so funny to look back at what was ‘in style’!” – Catherine F.

Rocket Dog

“Freshman year of high school I thought Rocket Dog platform sandals were the COOLEST. I owned them in every color (obviously) and would wear them with Soffe shorts and a tank top thinking I looked super fly. Anyway, on the first day of high school, I strutted in rocking my Rocket Dogs and ate sh*t in the main entrance, right at the toes of a few disgusted senior girls. That was a definite fashion NO, but I wore those bad boys like, everyday.” – Nina R.

Total Prep

“Popped collars, what the hell was I thinking? I absolutely HAD to have two Abercrombie & Fitch shirts and the one underneath HAD to match the moose on the top shirt. Both collars were, of course, popped.” – Amanda T.

Cool Cowgirl

“Levis tucked in cowgirl boots. That was hot my ninth grade year of high school!” – Lisa S.

Punk Rocker

“My best friend Megan and I used to wear red pleather mini-skirts and fishnet stockings to church. Her Mom would encourage us to be acolytes, and I'm pretty sure it had something to do with the fact that we had to wear long robes that covered us from our neck to our toes. She also dyed my hair pink once the night before we went on vacation. I think the most ridiculous thing we did, however, was run around with children's purses, like ones with Elmo and The Little Mermaid on them, when we were old enough to drive cars.” – Jasmine G.

Catholic Grunge

“When I was 14, I was really into the grunge look and went to a Catholic high school (read: uniforms). I was all for self-expression, so I brought my grunge love to my uniform via layering. I would wear brightly colored tights under my skirt and a fray-edged long-sleeve top under my shirt (with the sleeves rolled up, naturally). And the pièce de résistance? A homemade necklace made from cow bells.” – Sarah W.

Spring Breaker

"Back in high school, my friends and I all thought it was so hot to wear tight little tube tops with short mini skirts. So obviously my go-to Spring Break wardrobe consisted of just that. Looking back, I'm really not sure WHAT I was thinking. One thing I do know for sure is, I definitely thought I was killing it in the style department then!" – Elizabeth M.


Tell us, what are some of your fashion moments you'll never live down?

image via imaxtree