Describe your most embarrassing outfit!

Please describe an outfit you wore, from age 13 or older, which you thought was cool at the time but are now very embarrassed that you wore that stuff.

Mine, I wore a bolo tie, an oversize T-shirt, high waisted tapered leg jeans with Nike basketball shoes. I was 15 at the time. Very sad indeed.

Yes 22
No 16
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Comments ( 22 )
  • howaminotmyself

    I've been a jeans and t-shirt kind of gal for years. But there are photos of me in my favorite outfit when I was 12 or so. Hot pink leggings with an oversized turquoise sweater. That sweater had pink televisions and tv knobs for buttons. I was cool. Hehe.

    And I have plans with the housemates to go to a thrift store and find embarrassing outfits and take awkward family photos with our children to pull out when they start misbehaving in adolesence.

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    • charli.m

      That is brilliant!

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  • dirtybirdy

    Oh dear. I'll keep quiet here.

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    • NotStrangeBird

      Admit it, you dyed your feathers pink when you were going through your "flamingo phase".

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      • dirtybirdy

        This is my flamingo phase.

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        • NotStrangeBird

          So you've gotten past your black-dyed-feather-goth-crow phase then?

          Rich & Chris Robinson will be disappointed.

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          • dirtybirdy

            But i paint my eyes as black as night now. That counts right?! The pink is gone you see, no shramps.

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  • NotStrangeBird

    Two words: Plaid Pants.

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  • BugattiFan3B

    When i was 12 i wore high waisted jeans tht went up to my belly button and a short shirt that didnt go down very far. People could see my skin on my stomach and tried to have sex with me. So fuck that!

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  • Ibelievethis

    I can't believe I am about to admit this even under the disguise of my user name but here goes... A green tracksuit with teddy bear on it. I was 13 My mum bought it for me and I quite liked it at the time and I was so good as a kid I wouldn't have dreamed of kicking up a fuss. xxx

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  • RomeoDeMontague

    I don't think I am embarrassed of any of them. Some of them are nicer but none I am embarrassed of.

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  • Skitzo1

    Jean shorts, knee high white socks, brown steel toe-cap boots, blue and white chequered shirt, suspenders with a red bow tie and a helicopter beanie hat.

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  • hitachiin99

    I really don't care about my looks much, but this is outfit was horrid.

    I wore a really cute sweater, with jeans.. and my ugly tennis shoes. It totally made me look like an idiot.

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  • robbieforgotpw

    I wear trash bags.

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  • Epofly

    Um, I had one of those one-piece sweater vest/collared shirt pieces, and I'd wear a pink and black plaid skirt. Both bought from Wal-mart off my cat-sitting money. My hair was also colored a bright red, which made the outfit worse. I thought I looked "intellectual" back then.

    No.

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  • GuessWho

    I've never worn any embarrassing outfits.
    I wonder if I'm missing out on something...

    The worst case for me has been forgetting to zip up my fly, but that's not really embarrassing because people usually don't notice before I do and zip it back up myself anyway.

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  • Anime7

    I use to be in cross country, and I had these extremely short shorts. These shorts barely covered anything, and my friends got a good laugh whenever they saw me in it. Personally I though they were comfy, I could see why girls wear short shorts.

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  • Anything my mother forced me to wear or did to my hair. I was the only eight-year-old in my school who had a short-hair perm. I looked liked like the orphan Annie.

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  • Pika-girl

    Umm... I don't know if this really looked nice, but it was my favorite when I was 7.
    A black and white plaid with a sparkly buckle. It was above knee-length and was tight. I wore knee-high black socks with white ribbons on the edge. I wore black boots with metallic buckles that hold straps. Then, I wore a black/white bow headband (bow on the left).

    For a 90's party on 2012, I had to wear a hot pink tank top with a loose, white, stomach-length shirt that had a pink smiley-face that wore heart sunglasses and stuck it's tounge out. I wore black tights (my usual everyday pants) with an over knee-length hot pink skirt. I wore colorful shoes and a big zebra-patterned bow on my head. I didn't know what I was doing... Did I do it right?

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  • Thexoutcast

    Fitted plush pink turtleneck sweater. Tan textured skirt. Baby blue tights with naked angel babies printed on them. Tan platform shoes.
    Completely serious.
    I thought i was being creative.

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  • Holzman67

    Hmm I don't have anything from the age bracket you asked.

    There is film footage of me on a vacation in America when I was 10 years old, dressed in bicycle shorts and a bumbag. I find it very embarrassing, but it was the early 90's so I do have that on my side!

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  • squirelhunter

    Wait oversized t shirt tampered jeans and bolo tie with high tops is embarrassing? This is news to me

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