Rocking the First Day of School

By Jessica Thompson August 15, 2013 10:34 AM
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Ah, it’s back to school time. Even though I have been out of school for years, the school calendar is firmly imprinted on my brain. This time of year will forever feel like a winding down of the carefree days of summer and the start of a more serious cycle in time. Even though my job stays the same from month-to-month, I still feel that first day of school anticipation on behalf of current students. What a beautiful mix of anxiety and hope and curiosity!

The first day of school was always such a big deal. I remember my first day of seventh grade very clearly. In my school district, seventh grade was the start of middle school. I had to take a bus to a larger, farther away building with lockers and warning bells and passing periods and deans and way more students. I was nervous as hell. What if I couldn’t find one of my classes? What if my locker wouldn’t open? Did we really have to change clothes for gym? What if people stared at me while I was changing?


It turned out these shoes were only “cool” because they were Jordans, and if you had the Payless version everyone would just comment on how big your feet looked

I planned out the perfect outfit for my first day. The year was 1993 and my outfit was about as 90s as you could get. I wore large, knock-off Jordans from Payless that a cute boy in my English class immediately referred to as “boat shoes.” With those shoes I wore red and green socks. No, not a single pair of socks that contained both green and red–two pairs of socks, stacked on top of each other, one in each color on each foot.

Each pair of socks matched a leg in my knit shorts. That’s right, my shorts had one red leg and one green leg. I paired them with a Christian knock-off Cross Colours t-shirt my mom had bought me in lieu of the real Cross Colours shirt I wanted. Instead of saying the brand name “Cross Colours” across the chest it said, “Cross over to Jesus. Isn’t it time?”


My fashion inspiration for the first-day-of-school in 7th grade.


Once I arrived to middle school for the first time, I faced an awful shock. The “fashion climate,” if you will, was vastly different there than it had been in my elementary school. While hip-hop fashion was de rigueur in 5th and 6th grade, preppy fashion was “in” at this new place. All of the people who immediately positioned themselves as “cool” balked at my outfit and called me “ghetto” as i stood there stunned, watching them walk away in their khakis and GAP t-shirts and penny loafers.

I vowed not to make the same mistake two years later on the first day of high school. The summer prior I stocked up on copies of Teen and Seventeen and resolved to wear something “trendy.” You know how those magazines always have quizzes you can take with categories they place your in? Like, it’d tell you if you were preppy or sporty or alternative or flirty or whatever? Well, I wanted to be preppy. At the time (1995), all the fashion magazines were saying sweater vests were the rage for preppies. Naturally, I bought one.


I couldn’t find any 90s photos of this trend, but here’s a current version on sale at And yes, this is from the boys department.

On the first day of high school I had on my perfectly planned brown leather shoes, the right faded shade of denim jeans, and my red, Fair Isle-print sweater vest. I walked out of the house thinking I was golden, only to quickly find out I had failed again.

None of the magazines had mentioned sweater vests were only cool if you wore shirts under them!

I wore my thick sweater vest on its own, as a shirt. Not only was it hot (this was August in Chicago in a building without air conditioning turned on), but it was itchy! I spent half of the day trying not to scratch myself and staring dumbly at the people who kept asking, “How come you don’t have a shirt on under your vest?” Also I hadn’t washed the vest after buying it, so pills of lint kept rubbing off of it. That combined with my sweatiness meant half-way through the day I walked into the bathroom to find my freshly-shaven armpits looking like they were full of reddish-brown gorilla-sized armpit hair! NOT COOL!

That experience my freshman year of high school coupled with the insecurities of middle school pushed me to give up on chasing trends altogether. I realized that I wasn’t very good at trends anyway, and that trying so hard made me feel even worse about myself. As an early teen I chased trends because I wanted to be cool. I hadn’t yet realized that trying hard to be cool is about the least cool thing you can possibly do. To all of the girls out there who are still in middle school and high school, know that confidence is what what makes you hot. It might be hard to believe from where you are now, but it is true. If you’ve got it, what you wear will become a trend. Trying to follow certain trends in order to look cool (versus dressing how you like and knowing you are cool no matter what you wear) will only perpetuate your insecurities as you wonder if what you’ve chosen is “in” or “out” at the moment. The sooner you learn this, the happier you will be. Learn from my mistakes!

If you feel like wearing something trendy, go for it. And if you feel like wearing something not-trendy, go for that too! Just walk tall with your head up and smile. That is what matters the most. Have a great school year!

Jessica Thompson is a writer and dog-lover living in Chicago. She is co-owner and Editor of What Song is in that Commercial? She also does freelance blogging and social media and may be reached through her website,

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