Why You Looked Weird in High School

An Illustrated Guide

by Jaya Saxena, with pictures by Matt Lubchansky

My first day of high school was also the first time I really embraced the idea that you could change your whole image just by changing your clothes. I decided it was finally time for me to be punk rock, and I chose the most Punk 101 outfit imaginable: black T-shirt, plaid skirt, fishnets, boots. It seemed simple enough to execute, something to get me in the door as I amassed a collection of studded belts and patches. Unfortunately, execution is everything, and I wound up looking more like a slightly edgy nun. The fishnets were easy enough, but the plaid skirt I made in summer camp came down to my knees. It turned out I didn’t own a black T-shirt, so I had to borrow something from my mom, a ¾ sleeved boat neck thing from Banana Republic that sat too baggy across my chest. The boots were also my mom’s elastic ankle boots. I hadn’t yet saved up for the Doc Martens. Suffice it to say, the punk contingent did not embrace me that year.

I figured it couldn’t just be me, so I asked some friends if they had similar experiences. Most of us tried valiantly, as teenagers, to manage our image through clothes—and unsurprisingly, lots of us didn’t seem to know what we were doing.

Sophomore year of high school, I was committed to starting off the school year as sexily as possible, which obviously meant dressing up in a Catholic school uniform. I went to a large, diverse public high school, where clothes ran the gamut from “trendy” to “slightly less trendy,” but for some reason I knew that a black vest over a white button down, a red plaid skirt, and black boots was all I needed to be “cool.” I plotted all summer, and strolled into school, confident, sexily (in my head) (I was 13), and…no one noticed. Well, actually, one person noticed, but just said, behind my back, “what is this? Sacred Heart?” I put the skirt in the back of my closet, and remained uncool. Even now, I ricochet between deciding if I care about my personal style and if I don’t. Whenever I’m shopping, I just ask myself, “Would a cool grandma wear this?” If yes, I buy it. I think that means I probably wouldn’t purchase a red plaid skirt today. — Jazmine Hughes, 22, from New Haven, CT

I probably wore my Bad Emily zip up hoodie. I had that thing for years. I don’t think I was consciously trying to be “skater” or whatever but I definitely was like, cute but laid back and not trying too hard. . .I was super conscious of my walk because I was growing hips, so I downplayed it by wearing guys jeans and being “one of the dudes” but in a femme way. — Whitney Johnson, 28, from Los Angeles, CA

I was never cool in my hometown and my classmates every year were the same so I was basically stuck how I was. But I did go to a new summer camp when I was 14, and was very, very ready. My mom helped.

Let’s start at the bottom:

VERY COOL SKATEBOARDING SHOES because I was a very cool skateboarder. Just skating around town and not falling flat on my face every time I tried to do a manual.

HIGH WHITE SOCKS: because nobody told me any better and I liked how they felt.

SHORTS: long as hell. Pockets everywhere. It’s 2000.

NOT QUITE A HAWAIIAN SHIRT: Definitely from a Pacific Sunwear. Definitely had a dragon on the back. Definitely rayon.

GOLD STUD EARRING: my mom took me.

CLIP-ON SUNGLASSES: Because the future is too bright to look at.

ADIDAS VISOR: A little innovation I had to show off the coup-de-grace,

FROSTED TIPS: though my hair is far too thick for this so it was really like a nice little blonde cap.

Somehow this look did not work. — Matt Lubchansky, 28, from Monroe, CT

Why was a boat necked shirt dowdy instead of hardcore? Why does a visor work on LFO and not on us? Are we doomed never to know what our clothing is saying, or is everyone I know just supremely bad at it?


A few weeks ago Anne Helen Petersen wrote a piece about the semiotics of Tinder, examining “why we swipe the way we swipe.” With Tinder, there is no text-based profile: “you have only the presence of a pair of pleated khaki pants to tell you if the person is, say, conservative, ‘a douche,’ and thus unattractive.” She set up a Tinder analogue featuring stock photos, and asked volunteers to explain why they swiped “no” when they did. As it turned out, people generated a slew of assumptions about education level, class, religion, and lifestyle based on a single photograph. Petersen argues these assumptions have “more to do with a combination of our deepest subconscious biases and with our most overt and uncharitable personal politics” than some unclassifiable genital urge.

But should we feel bad for judging Tinder users on the image they present? After all, these aren’t just photos, but the photos people chose in order to attract their ideal partners. We only get to judge these cultural signifiers because these are the ones the users wanted us to see. Petersen’s “Jimmy” doesn’t seem just like a “Southern” and “working-class” guy because he’s wearing a wifebeater and posing in front of a truck, but because, by including those elements in the photo, he’s telling us they’re important to him. He feels he looks good in this shirt, and he’s proud of his truck. The same goes for “Dave” and his golf bros or “Johanna” and her head covering. If you think you’d have nothing in common with these people, it’s partially because of how they look, but also because, by choosing that photo, they’re telling you what they value.

There are certainly factors beyond our control. You can’t change the color of your skin or your height, and changing your weight takes a long time. People didn’t respond as well to a girl with “cheap highlights and unfixed teeth,” but perhaps she can’t afford orthodontia or a better hairdresser. And of course, no one should have to change their weight or class or skin color to find companionship. But when we see each other on Tinder, presumably trying to look our “best,” we often see both things: what someone is trying to present, and how well it’s working.


Move-in day at my southern college meant it was 90 degrees and full humidity, with a 100 percent chance of me hiking up six flights of stairs with various plastic shelving units and suitcases. A dress would not have been practical, so I opted for knee-length shorts and a tank top, both of which were black. My mom tried to tell me that the combination might be a bit intimidating, but I can’t express how much I didn’t understand her. It was black shorts and a black tank top, the most basic outfit of all. What could be scary about that?

Years later, a friend of mine admitted she was in fact intimidated when she first met me, explaining how the all-black contrasted with her Vera Bradley purse and fondness for florals. We laughed as I tried to explain that it was the most practical outfit I owned for the situation.

A few more of my friends had similar tales of accidentally projecting the wrong image.

I don’t have any good stories about trying to craft a new identity through my clothes because I have never even really TRIED to do that. But I did wear jean shorts until I was 22 simply because nobody could ever give me a satisfactory explanation about why I shouldn’t wear jean shorts. Nobody could tell me WHY it was that jean shorts were fine in 2002, and then NOT fine in 2009, except that suddenly, without my knowing about it, jean shorts communicated something different. Before jean shorts just communicated “Hey, I’m just a regular dude wearing shorts!” and that morphed into “Hey, I’m a fat moron that can’t dress himself!” — Matt Chester, 27, from Chappaqua, NY

Senior year of high school, I wore sandals every day of the year [in Colorado]. That was kind of my way of showing I didn’t care what anyone thought about me. I had plenty of friends, but no close ones. Wearing sandals in the middle of winter was me saying I didn’t need a group of friends, I was fine on my own. Or I was just stupid and lazy. — Dan Jay, 29, from Loveland, CO

Even when we’re not trying to present anything, we wind up saying something. That girl with the cheap highlights may not be able to afford better ones, but she also might just like how they look, and not realize that other people consider it a marker of class. When I talked to my friends about our inept fumblings with crafting an image, one refrain kept coming up: “Nobody told me.” We may wear or do things not because we get great reactions, but because we’ve never received feedback at all.

Was I trying to say something with the tank top and shorts? Black was an acceptable color to wear where I was from, and though I ditched the nun skirt I was still experimenting with punk rock. The outfit said I was trying to be practical, that I didn’t feel like dressing up for anyone I met. The outfit said I was from the North. The shorts said you could expect me to dress in “boyish” things, and their wear and tear perhaps showed I wasn’t interested in new things either. These were all true things about me, I wasn’t trying to portray anything false or contrived, but that doesn’t mean I wasn’t subconsciously playing them up. There’s a difference between not trying to hide who you are and making sure others get the message.

The key to any good performance is intention. We choose our clothes based on what we want the world to see, sometimes before our inner selves match the outer picture. I couldn’t live up to the punk rock image when I was 14 because I was timid and awkward and called my mom before going out at night. (And borrowed her clothes.) The look is what I valued, but a second of talking to me showed you it wasn’t who I was—not yet. By college there I was, wearing all black, intimidating those around me, convincing people I was confident and hard, and starting to convince myself a bit of the same.

We want to believe that the person in front of us is who they say they are, and maybe we know that’s never true, which makes the lie more intoxicating. We hope for authenticity of self in others, because perhaps we may one day have that for ourselves. At the same time, we’re on the lookout for any tear in the facade, ready to rip it down and congratulate ourselves for spotting it, hoping that no one will turn the same eye to us before our inner and outer selves match.


Despite my flailing attempts to be punk rock in high school, I saw no apparent irony in mocking the popular girls for trying so hard. The perfectly straight hair and perfectly curled eyelashes—it all seemed so effortful, so deliberate. It had to be, right? And when I caught a glimpse of a queen bee’s Clinique waterproof makeup set on a school-mandated camping trip, I felt vindicated. Makeup for camping. The person she was trying to present to the world was a lie, and we’d give her hell for it.

I shared a tent with her on that camping trip, feeling guilty but also superior for packing strawberry ChapStick as my only “beauty” supply. She was visibly uncomfortable as we set up our sleeping bags under a tarp strung between a few trees. Camping wasn’t exactly my scene either, but I gave myself credit for being game. My kayaking gear was pretty similar to everything I wore at school—baggy tshirts, baggier jeans, nondescript sneakers. My hair was in braided pigtails to avoid dealing with the thickness and curls. Despite our woodsy setting, I figured the weekend would be a lot like high school, where I was ignored but certainly not hated. This seemed fine at the time, because at least (I told myself) I didn’t care.

The next morning, I woke up to see my tent-mate hiking back to the camp grounds after washing her hair in the water pump. She wore a set of grey, thermal long johns, the sort that you’d beg your mom not to order from the Hanna Andersson catalog, that clung to her bra-less figure like wet silk. I imagined what I’d look like in the same outfit, the tight, tapered pants showing off my thick thighs, elastic waistbands cutting into my belly, nowhere to hide my fat. She giggled and raced her friends to the fire, as if self-consciousness hadn’t occurred to her, as everybody could just wear something like that without any repercussions. Her face looked flawless. I suddenly understood the waterproof makeup.

I spent the rest of our camping trip in too-large sweatpants and a windbreaker, eating lunch alone, and getting my period in the middle of our kayaking excursion. It was a banner day for yours truly. I watched the long johns girl, now looking very “sexy L.L. Bean catalog” in tight leggings and hiking boots, perching on a rock with her sandwich and surrounded by friends. To me there were no cracks in her fearlessness. To me the boldest thing a teenage girl could do was not be ashamed of her body. I’ll never know if that was real.

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