Fashion Sins I Committed as a Tween

Growing up, I was encouraged by my parents to “be myself.” The sentiment was sweet; but in practice, these hippie parenting techniques resulted in multiple fashion disasters. Instead of being myself, I was a little bit of everybody else. I suited up in trend-whore clothing and accessories, no matter how contrary these “fashions” were to whatever else I happened to wear that month, week, or day. I may occasionally pull a Shakespeare and wax philosophical about the ‘90s; but all that my tween wardrobe and Hamlet have in common is that they are both TRAGEDIES.

In no particular order:

Smiley face everything: If it could be worn and had a smiley face on it, I owned it. Smiley face jewelry. Smiley face Joe Boxer long underwear that I’d occasionally wear out of the house as PANTS. Smiley face scrunchy, for Christ’s sake. Worst of all, though, was the patent-leather smiley face book bag. I had it in “yellow on black,” which I (mistakenly) thought was alt.

Oversized t-shirt tucked into jeans and puffed out, with three-hole belt: The oversized t-shirt tucked into jeans and puffed out was how you were supposed to show that you had a nice, round ass – which I didn’t. In fact, I was pretty assless back then. The t-shirt was usually “borrowed” from a friend’s older brother, or my dad if I was desperate. Across my flat chest was “FILA” or “FuBu” or some other ridiculously shameful brand that I had no business wearing.

This ensemble was not complete without the black “leather” belt that had three holes punched throughout. This was the only type of belt that existed in 1998. I bought mine at a 300-square-foot shop that specialized in bootleg tapes. While there, I also purchased Jay Z’s Vol. 2: Hard Knock Life and a sticky bun.

Chain wallet: Chain wallets screamed, “I’m a ten-year-old badass.” My chain wallet could not be my everyday wallet, unfortunately. It typically didn’t fit into my back pocket unless I was wearing my brother’s hand-me-down JNCO jeans.

Non-prescription glasses with gold frames: This is where I start shame spiraling. So, I come from a multiracial family. I grew up pretty indifferent to this; rejecting every individual culture I counted as my own in favor of being “American.” My dad was “white” and my mom was “black” and that was as deep as I cared to understand it. That is, until I reached Junior High and all of my friends were Hispanic. I used my vague ethnic background as a means to become “the same” as everyone else. I used my grandmother’s birthplace (Panama, on an ARMY BASE) as my “in.” I pretended my last name was spelled “Georgopuloz,” because everyone knows that if you tack a “z” onto the end of your last name, it becomes Spanish. My middle name, ‘Hope,’ was now ‘Esperanza’.

The non-prescription glasses with gold frames are symbolic of the many imprudent purchases I made in the name of being Hispanic/”hood.” When paired with doorknocker earrings, my “nameplate” (kill me), and my baby hairs gelled down and sculpted onto my forehead; I was certified Boricua. I now realize that I was actually just a tween growing up in Park Slope, that all Brooklyn tweens dressed like that regardless of race, and that wearing fake reading glasses was not “hood,” no matter how blinged out they were.

Overalls: If I said overalls weren’t the worst, I’d be lying. There were endless ways to look like a tool in overalls. There was the “one strap undone” look, and the “roll up one side of the pant leg but not the other” thing. Not only did I own blue jean overalls like most confused ‘90s kids, I also owned a brown pair. Brown jean overalls.

Socks in general: None of my socks matched, ever. I was always wearing one loud-ass patterned sock with a white ankle sock from Puma or some similar athletic brand. I had gaudy holiday socks that I wore year round. All sock combinations had to be painfully mismatched in color, height, and thickness.

Visors: Visors randomly became “hip” again in the early 2000s. I worked at McDonald’s at the time and entertained the possibility of passing off my McDonald’s “headgear” as an ironic visor from a “hip” skate-kid store like Mr. Rag’s or Pac Sun. I owned one other visor – it was from Michigan State and I bought it for this dude after making out with him once; then decided to keep it because he “wasn’t my boyfriend.” Oops!

I spent my tween years making the Arquettes look like the Armanis. I can’t even begin to discuss the hair that accompanied these atrocities of fashion (think of all of the horrible things that can be done with bangs, and multiply that by 30). I may take frequent walks down Nostalgia Lane, but my rose-colored glasses can still recognize fugly. TC mark


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  • Michael Koh

    I'm so sad I have never had a smiley face t-shirt… or smiley face anything.

    • Kimberly


      This is for you.

    • Kathleen Gambo

      And you're a better person for it.

  • abr1125

    i used to doodle a smiley face, heart, and peace sign combination as if that was the coolest thing on earth. i also had tie-dye shirts with smiley faces on them and made my mom wash them so that i could wear them everyday. my older sister would rock the big flannel shirt and baggy jeans, and i was super jealous of her look.

  • Grace Jung

    This cracked me up.

  • Guest

    This is so funny! I can definitely relate. Whenever I look at pictures of myself as a teenager, I cringe and wonder why the hell my parents let me wear things I wore on a regular basis… I'm sure they were just as horrified at the time as I am looking back on it.

  • Heretica Neue

    I was so cool I had a chain wallet with TWO CHAINS. Beat THAT.

  • Caroline fernandez

    I too proudly rocked the smiley face tshirt (on a flat chest). Combined with a pair of jncos, this made me (think) I was the coolest kid in school!! If only I knew.. Oh and overalls.. I had red velvet overalls from the gap.. What was I thinking?! Why didn't anyone take us aside to talk these decisions over?! Parents should be trained in fashion policing, too… And hey, aren't overalls still kinda cool? Kiiinda?

  • Rachel C

    Oh smiley faces! I had a SF patch on a pair of jeans, and my fashion violation was lime green shorts overalls that I would pair with rainbow striped tights. Someone should have reported me.

  • Rachel Butters Scotch

    Brown jean overalls. Sweet jesus.

    My main fashion sin as a pre-teen was wearing bike shorts all day everyday. Also, overalls. Feels like we wouldn't have been friends in middle school. :(

  • Tara Lane

    SHORTALLS. and i saved up for them.

    • Humblecore

      I remember asking my mom for this specific outfit from Montgomery Ward (RIP):

      Denim shortalls – mid-wash, not #dark- or acid-
      White t-shirt
      Red and blue flannel button-down shirt (and I was VERY SPECIFIC that it had to be a button-down, as metal snaps would clash with my shortalls' hooks)

  • ahclevergirl

    green and white striped short-alls, black tee with a red heart on the front, jacketed by a flannel. Huge gold framed, thick lensed glasses and disgustingly long straggly hair to my waist. I was ten years old and likened myself to Rayanne Graff. I understand now that i was way more like Angela.

  • Gina

    I also loved a good smiley face. I wore silver lipstick and loved everything vaguely 60s. I had a chain belt that had plastic daisies on it that you clipped around your waist. I also had many different forms of overalls, but the worst were PINK VELOR OVERALLS. I would also sometime wear a shirt over my overalls, why didn't I just wear regular jeans? So many questions.

  • Stephanie Georgopulos

    OMG. Do not want to go on a liking/commenting frenzy, but all of these replies are like… making me feel not so alone and also making me question if I should start a support group.


    Silver Lipstick (YES and also OMG)
    Tie-Dye Smiley Face Shirt, def had this, it was way too big
    Red Velor Overalls, Shortalls, Pink Velor Overalls, all overalls everything, WEARING SHIRTS ON TOP OF OVERALLS, SRSLY, WTF, I so did that on a regular basis

    +1000 to you all.

  • granos

    I'd really like to see some photos of these atrocities! I worked at Merry Go Round and The Chess King in the 90s: I had the BEST collection of JNCO jeans and you bet they gave me pancake butt.

  • Amy Grace

    Please, someone else tell me they wore boxer shorts as legitimate leg apparel for ladies.

    • granos

      Summer 1991, Bart Simpson boxer, purchased at Kmart worn with mens Hanes Vneck. Oh Yeah I was srsly stylin'.

    • Kim

      omg, absolutely! With a black mock turtleneck and patent-leather all-black Oxfords laced with wide ribbons.

  • mertzy

    I remember having ungodly amounts of “cool” hair clips from Claire's – the worst might have been the ones with little Pillsbury Doughboys attached to them. I also had so many of these “mood bracelets” –… – now that I think about it, I'm pretty sure my group of friends posed for a picture like this for the STYLE section of my middle school yearbook. Which also included a picture featuring all the kids who happened to wear Abercrombie the day the style photos were being taken. THANKGOD I was wearing some AF and would be forever immortalized as stylish next to the hottest guys in middle school.

    Oh and coordinating the colored bands in my braces to match the season – orange/black for October, red/green for Christmas, etc. #cringe

    • Rachel Butters Scotch

      The colored bands, omg. I remember doing a rainbow of bands and it was “so cool”.

    • Stephanie Georgopulos

      like like like, never had braces, was so jealous of everyone i knew that color coordinated their bands

  • Max Shipley

    JNCOs, maybe a tech deck fingerboard, and the offspring— elementary school fantasy

  • Kathleen Gambo

    This really brings me back. A vivid memory that's stuck with me from when I was young was the first time I got ready for school with the intention of looking “cute” for some pre-pubescent boy I liked. The outfit consisted of a navy polyester tracksuit with two lime green stripes on the sleeve and side of pants, paired with a t-shirt sporting a large hologram kitten on it. Patent-leather mini-backpack with neon smileys on it in tow. Fresh ta Death.

    • Stephanie Georgopulos

      holy shit you just went there i love it

  • Julian Tully Alexander

    I say bring back the overalls. they were swaggin.

  • Humblecore

    One word: Skorts.

    • Sars

      Another word: Tankinis

  • Jasmine Nicodemus

    overalls with a pink or baby blue tank top that was too short, and boxers showing? obviously a fashionista in the making. don't forget the white sketchers with the stripes on the side, only the coolest girls had pink. (i didn't… i still fit in the little girls shoes, so i got silver sparkly ones cheaper. and people thought it was COOL. oh dear god…)

    • Stephanie Georgopulos

      i call that one 'the aaliyah w/ overalls.” fantastic.

  • 27sandgranola

    My mother had tie-dyed long johns. She bought me a matching pair. We were really cool.

  • S.

    I remember the days when my uniform was an ankle-length jean skirt, platform sneakers, and – you guessed it – a smiley face t-shirt. Also I only wore one earring because it was what I called “style.”

  • Tsubaki

    I had a denim vest with 14 pockets on it. I felt so cool wearing it, all plastered in pins and patches. What a nightmare…

  • Amanda

    Love the junior high reference. I remember that “Boricua” phase hahah

  • mia

    UGH, guilty of all of them except hispanic, funny you should mention Shakespeare however as my personal most shameful may be a dress frightfully similar to this, that I would wear with Adidas three stripes like I was too cool to care.

    how will we ever take our own kids seriously at this age? ew.

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