6 Back-to-School Outfits That Made Us Feel Invincible

The first day of school always brings such promise: that you’ll be noticed, that you’ll fall in with the right — or a more interesting — crowd, that you’ll capture your crush’s eye or assert yourself in class. And for many adolescents and teens, the easiest way to show you’ve changed over the summer is through your look — whether it’s dyeing your hair a shocking red (à la Angela Chase in My So-Called Life), getting rid of your glasses (She’s All That) or acquiring a whole new wardrobe (Mean Girls, Grease). Even if the whole-new-you feeling doesn’t last, there’s something to be said for feeling unstoppable your first day back. Ahead, we ask six fashion insiders about their best, worst, and most game-changing #BTS outfits.

Lyndsey Butler, designer at Veda:

Back to school is just an exciting time. It’s a fresh start, the possibilities seem endless. Wanting to put your best self forward at the beginning of the year totally makes sense. And I think it’s important. It sets the tone for the year ahead. Even though I wore a uniform — the same one for 12 years — my [first-day-of-school outfit] was very important to me. I wanted to stand out and look cool. When we were younger, it was all about wearing cool printed shorts, or boxers, under your skirt so you didn’t have to be too concerned when you were climbing trees or playing basketball during recess. Getting new knee socks was always a big treat. Oh, and backpacks: Those were one of the few ways you could add some flair. I got this graphic printed one from the Limited. That was a very big deal. Photos: Courtesy of Lyndsey Butler.

Connie Wang, fashion features director at Refinery29:

I was never really interested in my clothes until I started reading The Babysitter’s Club and became obsessed with Claudia Kishi. She was the first Asian I had seen who defined herself through her extracurricular interests, not how well she did in school. I would read and reread her outfit descriptions and copy them down in notebooks. I loved how she treated fashion like an art project and how she made her own jewelry, repurposed other people’s discards, and preferred the weird, offbeat purchases.

My parents indulged me by buying me a new outfit for the first day of school and let me pick whatever I wanted, as long as it was under a certain amount of money. Instead of Doc Martens or Abercrombie jeans, I tried to find things that no one else had, which was much less about looking unique and more about not wanting anyone else to know that I couldn’t afford Doc Martens or Abercrombie. I shopped in the boy’s sections, the junior’s sections, and the adult women’s sections for potential items — I spent the entire summer planning and budgeting for what I would buy and would do trial runs leading up to the first day of school to ensure that everything was perfect.

My most vivid memory was the summer leading into seventh grade. I remember buying a pair of greenish flares with really huge, low pockets, a pair of chunky-heeled loafers from Payless, a little boy’s striped tee, and a three-pack of tattoo chokers, all for under $50. I thought I looked like a Delia’s model. Photos: Courtesy of Connie Wang.

Erica Cerulo, co-founder of Of a Kind:

Back to school is a big deal: Growing up you’re figuring yourself out year after year. And you want to present yourself in a way that demonstrates to your peers how you evolved or changed since three months ago.

I thought a lot about what I would wear the first day of school, even though a lot of times it was just a white T-shirt and shorts. In grade school I would visit my grandparents in St. Louis over the summer, and my grandmother loved taking me to the Galleria to go shopping, and I remember contemplating a potential contender for my back-to-school outfit then.

When I was younger, in fourth, fifth, and sixth grades, I played soccer, and caring about clothes was really not cool. I was deemed really girly by my friends for wearing jean shorts instead of Umbros! And then junior year, I feel like all the best comments revolved around someone looking so tan, so people would wear a white shirt or turquoise to play that up.

But I was always interested in clothes: There’s a picture of me going to school in a purple mock turtleneck and little miniskirt with a paisley print, and it’s so much more of a look than I remember wearing at that age! I was about 8. Oh, and the backpack being coordinated and being so huge, with, like, 40 pounds of loose-leaf paper. Photos: Courtesy of Erica Cerulo.

Claire Mazur, co-founder of Of a Kind:

I was all about setting myself apart and looking weird and different and then regretting it when I was young! I distinctly remember going shopping at Gap Kids and how important it was to get a matching scrunchie and top for my outfit. I had one color or pattern from head to toe, and also a matching scrunch. That mentality has continued today: I still am matchy-matchy.

I remember in fifth grade going to the Gap around the time Clueless came out, and I got these knee-high socks and corduroy green overalls with a matching green cable-knit crew neck sweater. It was not flattering at all and was ridiculous because when school starts it’s not actually fall yet! But I was so psyched about this outfit that I wore it the first day of school. In high school, I wanted to be more sophisticated, and I borrowed my mom’s skirt and purse. In retrospect, it was a terrible outfit, but I needed to feel very chic. Photos: Courtesy of Claire Mazur.

Amber Doyle, custom tailor:

I went to a Catholic school through eighth grade, and I always wore funky shoes or crazy tights to make my uniform stand out. But I went to a public high school and got to wear whatever I wanted: I remember that pressure of getting dressed — I was curious and excited. I would come to school in costume. I think I realized really young, looking at fashion magazines growing up in this supersmall town outside of Chicago, that fashion was all about creating a fantasy, and I could create my own world with my clothes.

I actually thought everyone looked so cool in high school: You had the kids who wore the mod suit and tie, you had the kids who wore plaid bondage pants and green hair, and you had the preppy girls with polo shirts. It helped that I could make my own clothes: I did a little of everything. I remember one look with patterned tights and a mod dress. And another time I wore a pencil skirt and did my hair in pin-curls like a pin-up. I would wear patent leather and tease my hair like Siouxsie Sioux. I usually made my own clothes or bought vintage, but I remember in high school saving money to buy these reissued Vivienne Westwood pirate boots. I worked my butt off selling my clothes and babysitting to afford those shoes. And then nobody understood them! But I thought they were the biggest deal. Photos: Courtesy of Amber Doyle.

Lisa Mayock, co-founder of T-shirt company Monogram, former Vena Cava designer:

Planning my back-to-school outfits felt like the only good part about going back to school. I started planning my outfits at least a month before school started. I gleaned ideas from my Seventeen magazine subscription, and the Vogues and Bazaars that I went to the library to read. Around age 10, I discovered the Salvation Army and realized that I could approximate some of the editorials I liked so much. One year I made a dress from my best friend’s grandmother’s old curtains and another from a plaid Salvation Army muumuu. These things were all hand-sewn and literally about to fall off. They paired well with a Winona Ryder pixie cut and platform creepers in pale blue suede. [Those creepers were] special — my budget was about $50 to $60 for back-to-school stuff, but I bought them on Melrose for $60 and wore them until they fell apart.

The most outré pieces I made — a sequined paper skirt, sharkskin pants with a pink tulle overlay, a rust suede skirt with dozens of tiny squares cut out with an X-acto knife — I was too intimidated to actually wear, but just the act of making them felt bold and rebellious. Photos: Courtesy of Lisa Mayock.

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