I Dressed Like My High School Self for a Week

When I volunteered as tribute for the challenge of dressing like my high school self for a week, the first thing I did was open up Facebook and scroll back to the very beginning of my timeline. Facebook is a perfect time capsule of my high school self because I signed up for it my first week of ninth grade (September 10th, 2006, to be exact). I highly recommend a trip down your own digital memory lane because you might uncover a gem like this:

More importantly, though, I was able to track my high school sartorial pursuits with the exactitude that only photographic evidence can provide.


In addition to sporting a face the color of a vine-ripened tomato thanks to a hardcore anti-acne regimen, I was also a big fan of corduroy skirts. Although my parents were too cool to demand a photograph of me on my first day of ninth grade, I remember my outfit perfectly: light brown Rainbow flip flops, a gray corduroy skirt from American Eagle and an honest-to-goodness ribbon belt.

I was able to call stuff in and recreate it almost-to-a-T (who knew American Eagle would be selling the exact same skirt 11 years later)? When I wore it in the office, Amelia told me I looked like Marissa Cooper, which is everything the ghost of my early 2000s past could have possibly hoped for.


Like any sullen high schooler worth her salt, I obviously had a robust hooded sweatshirt collection, surpassed in quantity only by my bootcut corduroy pants collection. I called in a cream-colored pair from Boden for the purpose of this story. When I slipped them on, it felt like riding a bike. A bike with extremely rusty wheels. The low-rise waistband was alarming enough, but the medium amount of airspace between cuff and ankle (a.k.a. neither skinny nor wide-leg) was what really threw me. When I met up with a friend from high school for dinner that evening, she took one look at me and asked if I was en route to geometry class.


Tuesday’s outfit was child’s play compared to reentering the world of low-rise skinny jeans, which left me more terrified than ever at the prospect of their return. I think the universe was punishing me for writing that story because I sliced my thumb with a kitchen knife when I was cutting up an apple before trying them on. Do you know how hard it is to pull up and button skin-tight low-rise skinny jeans with a bleeding thumb? I’m still stressed just thinking about it.

I was in eighth grade when I saw low-rise skinnies for the first time. The coolest girl in my class was wearing them. They were from True Religion (which I did not know at the time, but in looking back I can clearly recall the tell-tale back pocket embroidery), and the waistband couldn’t have been more than two inches higher than her mons pubis. I was obsessed.

I purchased a pair of my own shortly thereafter from People’s Liberation, pictured in the above photo on the left, along with my teenaged backup dancers.


I felt a moral obligation to recreate the outfit I wore the first time I ever imbibed an entire alcoholic beverage. It was the spring of my sophomore year, my redness-provoking anti-acne regimen still going strong. I’m very upset that I can’t remember the brand of the artificially faded bootcut jeans I was wearing, because they were an integral character in my personal coming-of-age story. Please observe closely because there are RHINESTONE WINGS on the back pockets and I don’t want you to miss out on the opportunity to laugh at my teenage self’s expense.

I haven’t worn this particular denim silhouette since 2009, so you can imagine my surprise when I slipped on a pair of bootcut AGs and actually kind of…loved them? If there’s a chance they’re coming back, I’m not opposed.

I had plans after work to meet up with my boyfriend (who just so happens to be a former high school classmate). When I walked into his apartment, he immediately gestured at my jeans and said, “Are those new?”


The summer after sophomore year of high school, I distinctly remember being into BELTS, specifically those I could use to cinch dresses and blouses at the waist. I belted everything. I was a belting machine.

This red kaftan-esque dress is actually one of the very few items of clothing I haven’t thrown away from high school. As you can see in the above action shot from behind, I wore it belted. Thus, I belted it once again, for the first time in almost a decade, and probably the last.


On right: J.Crew t-shirtOn right: J.Crew t-shirt

I went through a phase the fall of my senior year wherein I dressed like a mime. This outfit was the easiest to replicate with my current wardrobe, because it is actually the only one I would consider wearing now from head to toe. I went to the movies with friends that evening and the only commentary from the peanut gallery was, “Aren’t you hot?” It was a fair question for someone wearing long sleeves and pants in August, but such is the life of an intrepid journalist.


2006-2010 was a simpler time, a time when the term “athleisure” was still a twinkle in our cultural lexicon’s eye, a time when Soffe shorts and SoLo pants were considered de riguer when it came to the crossover of athletic clothing and comfort. Those were the days! In homage, I donned a tiny pair of old gym shorts and a green fleece from my high school squash team that I’m frankly shocked I still have.

I regret to report I was unable to locate my retainer.

Photo by Louisiana Mei Gelpi.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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