A Painfully Enlightening Breakdown of My Back-to-School Outfits

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The smell of bus exhaust mixed with morning dew. The delightful bite of a September morning. The absence of summer; its roots. Everything is open and new. Backpacks are full of untouched notebooks with fresh edges and college-ruled lines. If I close my eyes and manifest it deeply enough, I can smell the burnt tip of a pencil and its curled remnants after a good sharpening. I can feel the waxy sureness of gel pens in my fingers and the new locker combination anxiety creep up my spine.

And you know what else I remember with the purest fondness? First day of school outfits.

Folks, they were something of the glorified past.

All throughout my childhood and high school, I personally petitioned for comfort and epic trendsetting when it came to fashion. I hated pants until I was a tween. But when I became fond of them, I would have married a pair of flare jeans. August was a quiet, fashionable blessing every year, when my mom and I would hit up the mall for a beginning of the school year shopping spree. Favorite stores were as follows: Limited Too (if I was feeling poppy athleisure), Delia’s (remember how cool bottle cap necklaces were?!), Gap (for the basics), American Eagle (to keep up with the popular girls), Spencer’s Gifts (for my first “Hey, I’m Up Here” shirt), and Hot Topic (thanks be to Avril Lavigne). Honorable mentions include Charlotte Russe and Wet Seal, when I deeply needed to be Lauren from Laguna Beach. 

If I close my eyes and manifest it deeply enough, I can smell the burnt tip of a pencil and its curled remnants after a good sharpening. I can feel the waxy sureness of gel pens in my fingers and the new locker combination anxiety creep up my spine.

The first day of school was always monumental in this fashion journey. In grade school, I wanted nothing to do with clothes. By the time high school hit, I wanted to be respected by the popular girls. I knew exactly which ones; would plan walk-bys near their table at lunch so they could understand that I was just like them. I liked all of the things they liked! I listened to all the same music and could make them laugh! Look at my glitzy Silver jeans! They have no pockets on the butt!

Going back to school was an excruciatingly eager task. I wanted to be a hundred women at once: Britney Spears, Mischa Barton, Mary-Kate, Ashley, and in a quiet chasm of my heart: Avril Lavigne. I wanted to impress girls. I wanted to impress boys. I wanted to be effortless and complemented and a good friend. I wanted everything—which is all part of the first day of school outfit charm.

So, in order to fully understand the beauty of this transformation, let’s start from the beginning. First grade, when my style was like an Astro van—all about comfort.

Outfit #1 (First Grade): Matilda Wormwood Chic (photo above)

Starting fresh with my favorite outfit. Nothing tops a plum corduroy dress with rainbow buttons, first of all. Secondly, those loafers are the most kiddo-fashionable thing I’ve ever seen and I would wear a pair today?? Comfort is key here, as I know I refused to wear pants until I was at least thirteen. You can’t see here because I’m shielding from the sun but I was rocking some top-form, thick bangs.

Outfit #2 (Second Grade): Lumberjack Chaotic Good

Before diving into this one, can we first cordially appreciate the nineties wallpaper? Good work here, mom (Writer’s Note: Darla would beg to differ). Our kitchen was filled with painted peaches that looked like fist-sized baby butts and I loved showing my friends. We’d laugh about them always. I’m really jazzed my mom wanted to use it as a first day of school backdrop.

Anyway, this jacket was a wardrobe legend in my life. I wore it everywhere and refused to take it off. I loved that about being a kid. Articles of clothing and accessories became cherished and obsessive. You wore things to the ground. You can’t see it in this picture, but I had a plaid backpack I carried everywhere. Together, I looked like a blind lumberjack—with an entire row of missing teeth to add to the grunge aesthetic.

Outfit #3 (Third Grade): Laura Ingalls Wilder Meets Reebok White

A Painfully Enlightening Breakdown of My Back-to-School Outfits | Wit & Delight

I have a lot of feelings about this look. I remember this dress more than anything in my wardrobe at this age. It was my favorite frock, something that barely touched my body, wasn’t itchy and could pass as presentable in public (this was the age I still preferred waist high white tighties and waist high whitie tighties only). The shoes are incredible, as they may or may not be so clean they glow in the dark. And, let’s be honest, my sister’s hat is fierce.

Outfit #4 (Sixth Grade): The Adidas-Stripes-for-Life Lewk

This photo is a little dark but disposable cameras were chic in the nineties, okay! During this delicate time period, nothing else mattered but my brand new Adidas Stripes. You remember the ones. I wanted every single color. But I had to settle, first, with a knockoff Sketchers version that I hated. My parents didn’t understand the importance of my reputation in school and I had to beg them for a real pair. When I finally got them, I wore them every day with matching knee-high Adidas socks that only went up above my ankles because I had such defined calves as a young woman. I’d never played soccer, let alone enjoyed a team sport in my life, but joke’s on you if you thought I wasn’t going to look the part.

Outfit #5 (Seventh Grade): GirlBoy Fusion

I would say this was my peak awkward stage but, unfortunately, I hit that mountain top a year later. You can tell here that I wanted to be a girl but also had a soft passion for distant boyhood. I loved giant t-shirts that hid my middle school C-cups because I didn’t know what to do with the boy gaze. Therefore, I refused to pretend I’d never seen a Rugby game in my life and crossed my arms in photos to hide any evidence of womanhood.

Outfit #6 (Tenth Grade): Stripe Style City

The year was 2003. I was a sophomore. I had a fresh cut and highlights that looked like Smucker’s Goober PB&J stripes. A lot had changed since middle school. I was boy-obsessed and filled to the gills with girl drama. I was epically proud of my boobs and had no idea how to show them off without looking hideous. In a journal entry, I wrote about my desired style. “I really like wearing bright shirts and skirts,” I wrote in slanted cursive. “Shopping for clothes depends on my mood. If I want to be really girly and pretty, I go to Charlotte Russe or Deb. If I want to be sporty and summery, I go to Pac Sun or Buckle (if I can afford it). If I’m feeling less like myself, I’ll swing by Hot Topic.”

Outfit #7 (Twelfth Grade): Bangs and Bags

Legs for days, folks. There’s a lot to unpack here. First of all, what am I keeping in all of those bags?! I remember refusing to carry a backpack (too childish)! I opted for a briefcase and a very fuzzy purse instead. I had my first job as a sandwich artist at Subway, so this was the year I was able to purchase my entire outfit from Buckle, the coveted place in the mall that sold glitzy Silver jeans for $120 a pair—an astronomical amount of money when I was seventeen. I wore those gold flats, for example, until I blew a hole in their toes my college freshman year. This was also one of the first years of my life I got to carry keys, so I loaded them with keychains and swag. It drove my dad insane, because he thought I would ruin the ignition lock cylinders on my car. But, whatever dad! I’m a cool girl!

Looking through these old outfits and photos has reminded me of how much we can and do transform. Year by year, we find ourselves bursting out of the past into the unknown, finding fresh ways to express ourselves and become more and more of what we believe we can be.

Looking through these old outfits and photos has reminded me of how much we can and do transform. Year by year, we find ourselves bursting out of the past into the unknown, finding fresh ways to express ourselves and become more and more of what we believe we can be. That’s why this time of year has always been bittersweet for me. September opens a new page, even amidst a pandemic, to start in a new light. Alice Walker writes it best in her book In Search of Our Mothers’ Gardens, “Part of what existence means to me is knowing the difference between what I am now and what I was then. . . . To know is to exist: to exist is to be involved, to move about, to see the world with my own eyes.”

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