Fashion Sins I Committed In High School

Somewhere in between wearing overalls with one strap unfastened and… now, was high school–a time when my vanity (100%) and style (0%) were drastically disproportionate to one another. I was afflicted with Body Dysmophic Disorder’s conceited fashion twin – the worse I looked, the hotter I thought I was. Here are the fashion mistakes I made as a teen.

Wearing pajama pants as real pants: I can’t imagine what my rationale for this sartorial choice was. “If I wear nighttime garb to school, guys will imagine being in bed with me and… ask me to a movie?” After all, is there anything sexier than a teenage girl wearing maroon PJs adorned with assorted dogs? …Hopefully.

T-shirts: I owned a variety of tee shirts–some were sexually inappropriate and said things like, ‘Slippery When Wet,’ some were ringer tees that clung to my bicep and depicted something nostalgic that I wasn’t even alive for, like Hong Kong Phooey. I had a red t-shirt with a silver Superman ‘S’ on it that I wore on picture day despite my indifference toward superheroes. I basically owned every t-shirt sold in Hot Topic, Mr. Rags, Zumiez, and on occasion, Spencer’s. Shudder.

Jesus Is My Homeboy T-Shirt: I think you’ll agree that Jesus Is My Homeboy tees and the people who wore them have their own circle of hell reserved. This shirt was the perfect uniform to wear when parading my special brand of teenage hypocrisy: I hated church, I hated religion, and if Jesus weren’t such a chill wino, I’m sure I would’ve rallied against him, too. And yet! Did a week go by that I didn’t wear that shirt? Did I not, after determining that the shirt was ‘a hit,’ go out and purchase the complementary Mary Is My Homegirl shirt? You know I did. I’m just going to throw it out there that I was… young? That’s a good enough excuse, isn’t it?

Dog tags: Allow me to say that, in my (almost) 25 years, I’ve never done anything quite as moronic ‘in the name of love’ as go to the mall and get some guy’s name engraved on a dog tag and then proceed to wear it to school (sometimes beneath my shirt–closer to my heart and all that). The guy didn’t have to be my boyfriend, or even someone I’d made out with–just someone who I had a crush on. This was my way of saying, “Hey, I’m a hormonally-imbalanced psycho and OH MY GOD PLEASE, DON’T READ MY NECKLACE.” If I really liked the guy, I’d get a dog tag dotted with a cubic-zirconia for an extra $2. In my defense, engraved dog tags didn’t cost more than $5. My parents are selling their house and recently unearthed one of my dog tags that was engraved, “Save the world, baby. Save the world,” which I believe was ad copy from a Nike commercial that was popular back then. In other news: yes, I am a tool, and no, I have no shame.

UFO pants: Sure, I’d never been to a rave, but I wore UFOs with a sense of misplaced pride. It was just too cute to roll on E in pink raver pants, even if I was actually just going to school or hanging out around a bonfire in my friend’s backyard. The ‘room-y’ nature of these pants also made it easier to steal things from the mall.

Anything with a name brand on it: It didn’t matter what the article of clothing was, if it fit, where it came from, how old it was – if I could become a walking billboard for a corporation by wearing it, GIMME. Men’s Tommy Hilfiger polo? Check. Fleece GAP hoodie that said, “GAP” on the front in deliberately large lettering? Yup. Child-sized Northface bubble jacket that would cease to fit if I gained five pounds? Why the hell not. My mother enforced a strict “no brand-whore” policy while raising me, but her influence was moot once I began raking in a cool $250 every two weeks – selling my soul and French Fries at our local McDonald’s. I could finally afford all of the Macy’s clearance rack items I’d dreamt of. I was Nouveau Riche in its lowest form – teenager.

Pedal Pushers: Popularized during the ‘50s by bicyclists, ‘Pedal Pushers’ resurfaced in the early 2000s and were embraced by teenage girls who detested shorts (there were a lot of us). Wearing Pedal Pushers in the warmer months was totally on-trend – except if you were tall and unaware that you needed a longer inseam than most. Like moi. The Pedal Pushers would always hit mid-knee, and I always looked heinously gawky in them. They were the too-tall, awkward cousin of jorts.

Von Dutch Everything: I blame Jessica Simpson or Justin Timberlake or whoever’s fault it was—you steered America wrong. The week of my 16th Christmas, I remember coming off of some god-awful flu and heading straight 2 da mall to spend that Christmas cash I’d been sitting on all week. I spent $60 dollars on a two-toned (yellow, turquoise) Von Dutch hat. To be fair, the turquoise part was made of some kind of crushed-velvet material, which totally warrants my spending $60 on a trucker cap. I also owned a Von Dutch bowler bag, which was regifted to me brand-new by a friend who obviously knew much more about fashion than I did. TC mark


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  • Z.

    no uggs? i’m disappointed

    • Stephanie Georgopulos

      Not til college, my friend. 

  • Allison Berger

    Skirts over pants, man. Skirts over pants. 

    • guest

      I totally did this. Worse, dresses over jeans. I even had a stretchy skirt/pants combo piece. I stylishly wore it with nylon shirts and creepers. Oh the 90s. 

  • Puddles

    senior year i found a hannah montana t-shirt in my school’s lost and found (yeah, i raided the lost and found for clothes, whataboutit). i wore it the next day waiting for someone to recognize it….. didn’t go as planned

    i liked the first article better. funnier and the things you wore were more ridiculous. but still lolol :)

  • mashka

    yikes this reminds me of all the horrible fashion sins I committed. In middle school it was worse. In high school I distinctly remember this floor length DENIM skirt that I wore. With rhinestones on it. Yep.

    In middle school I wore pretty much everything you could possibly find at PacSun, I was a ~surfer girl~ at heart even though I lived on the East Coast and had never so much as touched a surfboard, I lived vicariously through Roxy ads in my Seventeen magazine.

    I wore ridiculous JNCO wide leg “skater” jeans from PacSun, even though I had only stepped on a skateboard once.

    Ahh, the list goes on.

  • kasie

    do yall remember those stretchy, plastic, lace-type choker necklaces with the matching bracelet? I remember going into 7th grade and girls with black nail polish, different colored hair and like their sweatshirts tied around their waist were still rocking them. Those were more of a 5th/6th grade thing for me.

  • Cpaz

    Dying laughing . This is my fabulous HS years in a nutshell. WHAT WERE WE THINKING? At least we were in the trenches together…with jesus our homeboy by our side, trucker hats and all. 

  • Dree

    I think the whole trucker hat travesty can be traced back to Ashton Kutcher – one of the many reasons he should be beaten with a stick.

    • Puddles

      but he’s so shinyyyyyyyyyyyy

  • stormyquin

    I owned a flannel shirt for everyday of the week and always wore my hair braided.  It was like My Name is Earl meets Moesha. :/

  • Kimx2030

    colourful fuzzy cotton “gym wear”
    top and bottom matched in bright neon colours

  • mutterhals

    I used to get into fights with my friend over who had the wider diameter pant leg. It was like wearing a dress on each leg.

  • Maxwell Smart

    I really like pedal pushers, actually. The rest of this list, though? ACK.

    My freshman year of high school, I was guilty of wearing those little newsboy/cabbie/old Irish man hats all the time. Looking back on that era of my life, I conclude that hats are awful on me.

    My junior year of high school, I went through a Dita von Teese worshipping phase and decided to wear nothing but red and black. I dyed my hair jet black as well, disregarding my Irish skin tone, and proceeded to spend several months being mistaken for a Chinese prostitute.

    • Michael O

      I like those and PJs.  If you mix that in with no make up, I see that you don’t care too much about your appearance, and therefore, are easier to approach and talk to.

  • Rayan Khayat

    Von Dutch…Oh god…

  • rockstarmdeath

    i’m glad to know just because i grew up in a small town in texas, that everyone committed the same fashion sins! pajama pants to school– the great equalizer of american youth

  • Briana

    My seventh grade fashion inspiration: the section of the Delia’s catalog featuring the ~*kewl*~ ringer tees.

    brb barfin’

  • illdoit

    jnco jeans, black tank top w a heart on it from delias (does that still exist?), and huge DC skater shoes that were probably for boys….I was clearly the toast of small town jersey.

    • Maya


  • martin

    hahahah. I dressed like i was going on a job interview all through highschool only to turn into a dreadlocked yippy (hippie/yuppy)… post highschool i was confused i must say. but i remember someone not to be named wearing blue-green rain boots and she wore them with anything i mean anything and never in the rain… which help’d solidify the inside joke of that’s something  S@#p#an!$ would wear.

  • Anonymous

    Oh my god I’m wearing a Jesus is my Homeboy tshirt right NOW and I graduated HS years ago. Somebody call the president or something, stop me.

  • Meagan

    There was a time that I owned a watch ring.  Thats right, a giant ring with a watch face

  • Heather Mckown

    When i was 14 i really wanted a mechanics shirt they were selling at hot topic (1999) but i couldn’t afford it so i bought the same shirt at sears and was going to put my own name patch on it, but the only patch with anything written on it was one that said “felon” so i wore a work shirt with a “felon” patch on it.  I pretended the name was spanish. 

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