Prompt Images

Is there anything more first day of school than the debut of a fresh outfit and shoes so new they still pinch? I think not. The Prompt Mag takes it back to grade school to answer the age-old question, “Who are you wearing?”

Jillian Conochan

Freshman year. New school. I had a bit of a head start because I joined the field hockey program, which began 3 weeks earlier, so at least I knew 9 people and a gym teacher.

It was the mid-90s and I had the tough, tough decision between a Hang Ten t-shirt, striped in an ocean blue gradient, or a mint green, rosebud-printed dress from American Eagle Outfitters. Each was a VERY BIG DEAL, as mall shopping was frowned upon in our frugal little house; why, United Outlet and JewelCo make perfectly decent garments, Jillian.

Ultimately I decided on the dress, but the t-shirt was probably day 2. I still have both items, which tells me that even though they were a splurge, they did indeed mean something to me.

Dennis William

I don’t have a great memory and I was not/did not consider myself to be a fashionable dresser during my school years. BUT, I do remember my junior year of high school. That summer I had attended my first big stadium concert, featuring the Foo Fighters and Red Hot Chili Peppers. I bought a shirt of the opening act, Blonde Redhead. I wore that shirt on the first day of school. I felt very hip, because it was a band no one knew about (indie cred) and it had a slightly provocative image (edgy). I felt very cool answering “What the hell is blonde redhead?” five times a day every time I wore it.

Jennifer Racusin

The year is 1996. The place is Wauwatosa, WI. I’m starting my sophomore year of high school. I have chosen a shirt based on its softness and its color. It’s forest green. It’s a fine knit. It came from Express at the mall. It’s basically a fuzzy, short sleeved polo shirt. I’ve paired it with these terribly unflattering wide legged khakis, a style which thankfully has not returned from the 90’s. My hair is chin length and frizzy. My glasses are too big for my face. I’m not entirely sure I think I look good. It’s more of a this as good as it’s going to get kind of thing. I’m serving “I hate this school and I hate these people and I’m not going to try and impress any of you” vibes. It’s a lot of angst wrapped in a very dorky looking package. I am really happy with that sweater shirt though, which is what elevated it to first day status and cemented itself in my memory bank.

Fashion Show Viktor GIF - Find & Share on GIPHY

Josh Bard

Like many 11 or 12 year old boys, I didn’t buy or necessarily choose most of my own clothes that were not jerseys or sports-related shirts. But I do remember picking out this awesome navy blue and neon green long sleeve shirt from Gap on a family shopping trip. The first school day opportunity I had, I put it on and prepared for the compliments to flow. They did not, because, most 11 and 12 year old boys didn’t care about the clothes any of us were wearing unless they were sports-related. But then someone noticed, and it wasn’t for the reasons I was hoping or expecting.

See, Rachel Shelly (name changed to protect the innocent) was wearing the same navy blue and neon green long sleeved shirt, from Gap, and more specifically the men’s section of Gap. But when a boy and a girl are wearing the same shirt on the same day in the same class, it doesn’t matter where that shirt came from, because the boy is now wearing a girls shirt. I could protest (I did) and but that’s how the history books will tell it to our children, and our children’s children, who will all be wearing the same unisex silver jumpsuits. I was born ahead of my time.

Kelaine Conochan

Okay. So, I’m in 6th grade. I wear a lot of flannel, plaid long shorts like a skater/surfer boy would have in 1993. Okay, it isn’t just “a lot.” It is pretty much ONLY flannel plaid shorts with unshapely pockets that bow out after you do laundry. But whatever, because it’s either those shorts or Umbros covering my still unshaven legs. But the first day of school was a little fancier than Umbros, you know? So I’m rocking the plaid shorts, and they’re hues of tan and brown and orange, and they reach my knee because I’m still very much dressing like a boy these days.

So. I get this t-shirt on vacation in Long Beach Island. It has the Lorax on the back, of Dr. Seuss fame. So, that cranky little environmentalist is just standing on a tree stump with a decorative paisley recycle symbol around him, doing his thing, shaking his damn head at the Onceler, who is basically Donald Trump but we didn’t know it back them. And it was the 90s, so anything environmentally conscious had to be on an organic cotton shirt, which was a purposefully off-white color. You know, to show that we didn’t fux with the bleaches.

On the front was a message written in the same blocky asymmetrical font as a Seuss book title. With no irony, because it was the early 90s and Alanis Morrissette hadn’t yet taught us what that was, it solidified my my 5th grade righteousness with a very forward assertion: I speak for the trees.

Erin Vail

For girls of a certain age, the ultimate sign of status was a piece of clothing from Limited Too. While I didn’t have an entire wardrobe from LT, I did get to wear the occasional tee or tank. On my first day of fourth grade, I was starting at a new school. I was nervous and excited, hopeful but terrified, and rocking quite possibly my greatest back to school ‘fit of all time: a black shirt from Limited Too with a tiny, subtle outline of a heart in rhinestones on the front, and shorts. The shirt was clearly a Limited Too acquisition, but it wasn’t obnoxious. The outfit read confident, but cool and comfortable. My first day of fourth grade was an all around success in that my outfit was well received, and I solidified my friendship with my best friend of life, Alexa, when we sat next to each other on the bus.

Posing Best Friends GIF by Laff - Find & Share on GIPHY

Thomas Viehe

Do you remember Keyshawn Johnson? I know, it’s hard for me, too. He was a big deal for some reason. Kept showing up in the middle of my regular middle school appetite of Rugrats, Doug, and Channel One. The camera would follow him racing under and arching football, cutting between the grass on a field, guiding the ball into his gentle hands, and then sitting, laid back, laughing alone on some bleachers.  I knew the shoes by the soles. Green with some texture. Forgot the brand, just went to the mall and lifted every tennis shoe up until I found the one that Keyshawn wore on TV.

I wasn’t an athlete. Sure, I hung tough on the playground when it came to shooting hoops. Fouled like the best of the fifth graders. But now I was moving to sixth grade, to middle school, where the Big Kids lived. I needed me some athletic tennis shoes. Show some style. Get those ladies interested. Yes, I’m embarrassed to admit now that my mind worked so feebly. But this is how all middle school boys’ minds worked, right? Wear the right pair of shoes and people’s opinions of you would change. Girls would swoon, boys would be friendly. Life would be better.

When I got to school, excited and ready to show off my feet, every single boy in my class had the Keyshawn shoes. Everyone had been brainwashed. No it wasn’t an alien invasion or some Russian plot. It was capitalism. And we’d all fallen for its oldest trick, buying our way into being another shadow in the crowd.

Los Angeles Model GIF by Much - Find & Share on GIPHY

Sarah Razner

In the mid-2000s my small city in Wisconsin got an American Eagle. For us, it was basically the coolest place young adults could shop, and my sisterssix and nine years older than mespent their money filling their wardrobe with it. Since I wanted to be cool and mature like them and not the awkward seventh grader I really was, when it came time for school shopping I asked my mom to let me get some of the clothes from there. As it’s hard to turn down one daughter when you’re letting the rest get clothes there, she allowed me to get a few pieces: a green t-shirt with a bungalow on it, and a graphic white t-shirt that paired with a pink zip-up sweatshirt.

What I really liked about shirt/sweatshirt combo was that it had the t-shirt had an vintage logo for an invented pizza shop called The Lion’s Den. Its font was medieval; its crest featured slices of pizza and cups of soda bordered by majestic lions. The sweatshirt mimicked it in a bold, varsity-type font. I felt like it was a retro, casual kind of cool.

I can’t exactly remember if I wore it on the first day of school, but I know for sure I showed it off within the first week. As I walked down the hall, I remembered feeling confident, as if my matching zip-up and t-shirt set made me the epitome of cool. When people asked me where I got it, I said with the upmost pride, American Eagle. Even after wearing it a few more times, the clothing ride stayed.

I believe it was that fall when one day, wearing it and feeling awesome about myself, I walked into the house after school to find my older sister at the kitchen counter. Her eye flicked to my t-shirt and she started laughing.

“What?” I asked, suddenly feeling self-conscious.

“The Lion’s Den?” She said. “That’s the store on the highway. You know, the adult one?

I did know. It was the one we snickered about as we drove past, and while I didn’t know exactly what they sold, I knew it wasn’t appropriate.

Now, the names clicked. “Oh my god.” I stared down at my shirt. What if other people knew it was the adult store? What were they thinking of me, I wondered?

She cackled in front of me again and pointed down. Hot, fast and we’re not lion, she said. They were the words below the crest, now taking on a new, innuendo-laced meaning. “How did Mom let you get that?”

“I don’t know,” I murmured, and when my sister told her, Mom shared my shock. Safe to say, if I hadn’t already decided to not wear it again and throw it in the rummage sale pile, she would’ve done it for me.

Zach Straus

From age 10 to age 14, I went to private school, and from age 10 to age 14, I had a bowl cut, which, from the age of 10 to 14, I thought was a cool bowl cut;  that I looked like Shawn* Hunter from Boy Meets World, but in reality, was very much an uncool bowl cut, and I looked like I was Stuart Minkus** from Boy Meets World. In my defense, it was a private school, and my class only had 15 people in it. Bare minimum, we all had emotional bowl cuts.

Said school only went to 8th grade, which meant upon graduation, we’d be kicked out into the scary, hairy world at large, and unless you were super-religious, you were headed to PUBLIC HIGH SCHOOL. The week before 9th grade started, everyone in my class was invited to a pool party, organized by a savvy mom who knew we needed a chance to be together one last time before high school ruined us and we turned into dumb, shitty people who were never friends again.*** Good call, Carol.****

The day before the pool party, in an act of equal parts 1) long-overdue-objective-assessment-of-personal-image, 2) young-closeted-gay-fear-of-being-discovered-or-different, and 3) banal-teen-hopeful-reinvention, I decided to cut my hair.

“4 on the top, 1 on the sides, leave some bangs so I can spike ’em up” I told the hairdresser in the Westridge Mall, which is what I heard an older teenager say to a different hairdresser, as I was waiting, a 16 (holy shit!) year old, who looked like he could be featured in Seventeen Magazine, or a JNCO ad, staring lazily at the camera, a spilled Big Gulp pouring onto the sidewalk while a Drew Barrymore-esque skater chick kickflipped over the mess.

The next day, my dad dropped me off outside the house, reinvented as fuck, soccer-shorts-as-swim-trunks on, Big Dogs***** towel rolled under my arm, future looking bright, hair looking tight. Deep breath. Walked through the open screen door. Grabbed an orange soda. Through the kitchen and back to the sliding door out onto the deck. Everyone was there. Everything was in place. 14 friends I’d seen practically every day for the past 4 years. 6 lingering parents talking about the Capital Campaign at the Civic Theatre. 1 brand-spanking-new-Clooney-cut me.

No one said a single thing, and I learned a valuable lesson.

A bowl cut may not be a great look, but at least it’s there for you to bury your fingers in while you cry in an upstairs half-bathroom, something I want to be clear I only know theoretically, because at that party, I was 14 and practically in high school, with a new adult look to match, so if Carol tells you differently, that she found me, feet braced against the door for extra safety, orange soda spilled on the bathmat, window open to the sounds of my childhood Marco-Poloing away without me, she’s a fucking liar and bitch, because I didn’t, okay? I didn’t.

*Sean? Shawn? Shaun? Shonn? Too many ways to spell Sean. I refuse to google it.
**His first name was Stuart. I had to google it.
***Which surprisingly didn’t happen to all of us.
****Not her real name.

…and you? Tweet us your most memorable first day ‘fits with the hashtag #BackToSchool!

The Prompt Staff

learn more
Share this story
About The Prompt
A sweet, sweet collective of writers, artists, podcasters, and other creatives. Sound like fun?
Learn more