Back-to-School Fashion and the Meaning Behind It

On many a frantic morning in my teenage years, my mother would yell upstairs from the kitchen for me to get dressed faster. “School isn’t a fashion show,” she’d say. Little did she know, the hallowed halls of my high school were indeed a runway — and my getting-ready process simply could not be rushed. Each day had a sartorial theme that I had painstakingly planned for weeks, even months.

One week, I embraced my newfound love for purple and wore a lavender-hued outfit each day. Another time, I discovered Baby Phat and wanted to be among the first to wear it to school. The cat pranced on the back of my bubble coat as I sauntered from class to class.

This newfound hobby only intensified on the first day back to school. For me, back-to-school outfits set the tone for the entire year, serving as a visual marker of one’s evolution. With my first-day-of-school ‘fit, I was presenting a new me who was cooler and more put-together than the year before.

After landing a job at Aldo, along with a 50-percent employee discount, I kicked off senior year with a deep-red handbag and matching knee-high boots paired with a cream sweater dress. I needed my outfit to signal maturity — I was 16 and had joined the workforce after all.

On the first day of sophomore year, I added a feminine twist to the preppy trend that would go on to define my generation. I walked into homeroom wearing a purple wrap dress with a striped scarf casually tossed around my neck, matching with my three best friends of course. That outfit sent the message that I was tapped in enough to know the trends shaping the zeitgeist, but creative enough to make them my own. Meanwhile, my friends and I, pictured below at the homecoming dance, were cementing ourselves as fashion girls (a family member had even affectionately named us the “Glam Squad”).

Still, my mother was right: I was in school to learn. My priority should’ve been classes like Creative Writing, Spanish, and (to my dismay) Algebra. I was not there to show off my latest purchases from the local mall. But style was a lesson of sorts for me.

As fate would have it, I’d fall deeply in love with fashion during that time and go on to work as a fashion editor at women’s lifestyle magazines. In fact, my current getting-ready process for New York Fashion Week closely resembles those frenzied mornings as a teenager, down to the weeks of outfit planning and last-minute, day-of changes.

Trends have shifted, faded, and returned, but what’s endured is my personal approach to style. As a teen, I knew intrinsically that fashion was deeply intertwined with identity. I was still discovering myself, yet at every turn, I was met with labels: my peers saw me as fun and friendly but very much a nerd; my teachers saw a talented writer and dancer with insurmountable stage fright; my guidance counselor saw a Black girl who was “overly ambitious” and wouldn’t get into a top college — and said as much.

Yet I knew who I was and yearned to define myself on my own terms. Fashion helped.

When I put on my back-to-school outfit, it was a way to broadcast my self image to the world. I wasn’t the anxious girl who was fighting doubts being projected onto me — I was powerful and chic and full of creativity and promise.

Years later, I settled into that grand vision of myself. I made it into a great college and worked my way up the ranks in fashion; I finally overcame my fear of public speaking; and though I am still very much a nerd, for the first time in my life, I kind of like it.

But long before I became this person, I dressed the part.

I continue to use fashion as a tool of self expression — and as a Black woman, it serves me well. When I put on a bright color, and it pops against my complexion, I’m showing my love for my deep skin tone despite beauty standards that still worship whiteness.

When I slip on a floral-print, puff-shouldered dress and sparkling metallic heels, I’m leaning into a soft, feminine aesthetic as a Black, career woman who is often branded as “strong” and “hard” when frankly, I don’t want to be.

When I step out to the Met Gala or the CFDA Awards with braids cascading down my back, I’m disrupting the myth that box braids are somehow not fancy enough for formal events. How can a style that’s such a sacred part of my culture, that’s so intricate and innovative not warrant a place on the red carpet?

Those days getting ready for school taught me a valuable style — and life — lesson about identity. Now, years later, I’m still dressing in a way that feels authentic to me with no regard for society’s labels. And I’m still taking way too long to get ready.

Jessica C. Andrews (she/her) is the senior content director of Shopping and PS UK. With more than 15 years of experience, her areas of expertise include fashion, shopping, and travel. Prior to joining PS, Jessica held senior roles at Teen Vogue, Refinery29, and Bustle and contributed to The New York Times, Elle, Vanity Fair, and Essence. She’s appeared on “Good Morning America,” NBC, and Fox 5 New York and spoken on various panels about fashion, hair, and Black culture.