Illustrations by Sarah K. Myers.

Throughout my teen years, I went to a small K-12 school in Kentucky where the bulk of my peers wore more-or-less the same kind of thing, had more-or-less the same kind of hair, and attended my bat mitzvah with the ginger politeness of child snorklers encountering their first manta rays. Being a somewhat overeager teenager, I tried my absolute hardest to look exactly like everybody else, a mission that was, at best, counterproductive.

As memory and photographic evidence allow, below are the ten dumbest ensembles I wore in high school, in no particular order. These memories are painful, but maybe there’s a lesson on “individualism” or “conviction” in here somewhere, buried deep within the brutal self-owns.


1. On an 11th grade class trip to Virginia, a photograph was taken of me in which I was wearing a weird patchwork skirt from Urban Outfitters, a too-tight navy polo t-shirt, a turquoise terrycloth Juicy Couture zip-up, extra-large pearl earrings, and a headband that blended in with my hair. There’s a largely unresolved tension here between the traditional and the passé, a garbled air of metaphysical confusion and general incorrectness that is rather intensified by the photograph’s location in front of Thomas Jefferson’s plantation.

Advertisement

Advertisement

Why did I wear this outfit? What, exactly, was I thinking at this moment? We’ll never know, because I only wrote in diaries when I was depressed or had a crush on someone.

2. During the December holidays one year in high school, somebody had an “ugly christmas sweater” party, and I somehow managed to miss the mark on even an intentionally bad outfit. While everyone else wore varying shades of Christmas colors, I opted for a turquoise zip-up embroidered with snowmen paired with bright magenta leggings underneath a denim miniskirt. What? On my feet, naturally, were open-toed nude platform heels. It might have been cool if I had bucked the dress code entirely, or like, run away to Seattle, but instead I twisted my ankle and went home.

3. When I was between 16 and 18 years old, I was photographed sitting on a boy’s lap at a bowling alley wearing two long-sleeved t-shirts layered over each other and a large dog tag necklace. I have no context for this.

4. In the years around 8th/9th/10th grade, I had a reliable uniform that I frequently fell back on: tight flared khaki pants from Abercrombie & Fitch, a variety of brightly-colored polos that got me several embarrassing “midriff” citations, and light brown closed-toe Birkenstock clogs. The khaki pant, when hemmed just so, flared gently over the clogs like a blanket draped over the back of a sleeping turtle. This, to me, was good.

5. In another photo from that fated 11th grade trip to our nation’s capitol, I had on a red t-shirt featuring a map of Israel, hand-cut at the neckline for that sexy off-the-shoulder look. I was also wearing very long striped shorts that came down just above my knees, so no, they weren’t capris, and I’m not sure if “shorts” is a totally accurate term, either. I do remember it being very important and cool that a single black bra strap was showing, although the very mature sensuality of that detail was undercut by the fact that I was essentially wearing board shorts and a weird oversized tee that implied I was extremely religious.

Advertisement

Advertisement

This look was paired with a large and fuzzy bright pink cross-body satchel that I had also recently purchased on the same teen tour of Israel where I had obtained and manually adjusted the aforementioned shirt, and where I had apparently learned to dress like this.

6. On the hunt for a boyfriend sophomore year, I opted to wear a completely unironic and very sexual “french maid” costume from one of those horny costume companies to a Halloween party in someone’s parents’ barn. A foolproof plan, I decided. My mom, after being assured by a friend that her well-adjusted daughter wore a french maid costume once, too, reluctantly allowed me to leave the house, shooting me a stricken glance as I walked out.

As it happens, my only memories of the party are drinking and then immediately spitting out a cup of homemade mead that my friend brewed in his closet (we were reading Beowulf in English) and then watching someone pee in a corner of the barn, so it probably would have been fine if my parents had instead grounded me forever.

7. My senior prom dress was actually kind of great—a poofy gold eyelet Betsey Johnson number, it was the fanciest dress I’d ever owned, and with some minor accessory adjustments (why did I think my shoes and bag also needed to be gold?) it could have been a genuinely fun look. The problem was more that I’d gotten a spray tan the day before—an extra-dark spray tan, accidentally—and was, as a result, almost exactly the same color as my dress and hair.

8. I was pretty involved in my regional Jewish youth group in high school. This was less out of a sense of spiritual zeal than because my best friend had convinced me to join with her, and weekend “conventions,” which took place across various exciting metropolises in Ohio and Kentucky, provided an entirely different set of friends and boys, none of whom asked me if I believed in Jesus Christ. It also provided an entirely different—and equally bad—set of fashion norms.

Advertisement

Advertisement

Style sponge that I was, I quickly found myself in a series of long swingy skirts and tight tanks layered under low-cut t-shirts, a really weird mix of pious and booby. Hair, too, was different—here we flaunted our curls, swapping gels and scrunching furiously before tromping off to shul with glistening wet hair, dreaming of sex.

9. Shortly after graduating from high school, I went to Bonnaroo with a group of friends. Well aware that this was (sadly) the coolest thing I’d ever done, I tried diligently to construct the coolest outfit I’d ever worn. This was: a string bikini, a t-shirt (hand-cut at the neck, again) from a museum in Spain, aviator sunglasses that were many inches too big for my face, and yet another headband. In an unprecedented move, I layered my everyday understated gold lotus necklace underneath another, larger silver disk necklace that I had recently purchased at Target, a pairing that demonstrated that I was a rule-breaker and an original.

Advertisement

Is this the worst outfit in the world? Certainly not. Is it devastating that it was the best I could do? I think so.

10. I don’t know if there exists a more humiliating scenario than arriving at school at the nearly-adult age of 17 in a homemade t-shirt that reads “I’m Looking Fo a Dime” over a picture of a stiletto, but that’s what I did, and I have no excuse. My friend made these shirts for a big group of girls and gave everyone a different lyric; it was a “joke,” but also not at all a joke, and when we marched into calculus in our remarkably stupid version of the Pink Ladies jacket, I can’t lie to you—I felt cool as hell.

Advertisement

Advertisement

That feeling has since faded.