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-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.

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  • hearceespeak

    This is fantastic

  • Cristina

    I am living for Tuesday. Totally “i woke up like dis”

  • Jacqueline Melendez

    Maybe the jeans are Miss Me jeans? Everyone in my high school wore them and like their signature style is bedazzled back pockets

    • Harling Ross

      i think the brand started with a “P” i have no clue what it could be though!

      • catsandlipstick

        Paris Blues?

        • Harling Ross

          Ahh noooo ugh I wish I could remember

      • Tricia

        They look like antik denim or rock and republic. I rotated through both in high school– before Gemma Teller made them biker chic

      • Tennis Warhol


  • Adrianna

    I pretty much dress the same way I did in high school because I still own and wear most of that wardrobe, minus the flared jeans. (I’m 28, went to high school 2003-2007)

  • Andrea Raymer

    outfit 1 is what I have been wanting to dress like all summer. in fact I wore a denim mini skirt and polo just last week inspired by Lo Bosworth’s outfit when she and LC went to Sephora in the mall in episode 4 of laguna beach. I wore many of these exact outfits circa 2007. So much corduroy and polos were worn and I also went through a mime phase, except I called it a gondolier phase.

    side note: I recently wore Soffe shorts for the first time in a half a decade and I did not enjoy the experience.

    • Hayley

      Never liked Soffe shorts, never will.

      • gracesface

        i remember the challenge of seeing if i could fold them over THREE times. ugh, what a struggle.

      • A Local Honey

        So much summer cheer camp happened in Soffe’s.

        • elpug

          omg yes and some girls had patterned ones

    • Harling Ross

      lol to gondolier phase

  • Katie M

    I am very much into Thursday, the yellow/black/white combo is kinda giving off a Cher vibe? Maybe it’s because I was and still am very much a belting machine but Friday is also top notch 🙂

  • Quinn Halman

    Thank you for bringing Soffe shorts back into my consciousness

    • Harling Ross

      truly one of my greatest contributions to the internet in 2017

  • Liz Negrete

    Haha im a belting machine myself, i wonder if I’ll ever evolve from being one.

  • Abbie

    Harling, this is so perfect. This stuff is ALL GOING TO COME BACK–except please not the bellybutton piercings. Maybe that was just my high school? I was the ONLY girl on the cheer leading squad without a piercing. Now that I’m 30 and 2 babies later I am SOOO glad my parents forbade that.

    Soffe shorts were AWESOME. Mandatory roll down on the waistband.

    • Harling Ross

      omg yes to the roll down

  • Dulce Partida

    Now a I want to do it!

    • Harling Ross

      DO IT

  • Tessa

    Ugh now I want to do my own version of this with my daily high school uniform of my dad’s sweaters, a dress code-defying black miniskirt, black opaque tights with a littany of holes topped with a pair of costco wool socks and a-size-too-big doc martens, all garnished with food-coop-mom style costume jewelry. I was the terror of the third floor hallway.

    • Harling Ross

      hahaha the third floor hallway. we had one of those too! i wish i had been the terror of it so badly.

  • Michelle

    Love this, and also: MR is SO GOOD right now!!

    • Harling Ross


  • Courtney Johnson

    YES – I owned multiple corduroy skirts, pants, and some sort of blazer jacket if I recall. I grew up in Florida so I’m not really sure why that was a necessary look for me.

  • Lizzie

    Marissa coops 4-Eva
    I’m definitely planning to watch the first season of the OC with a bottle of wine this evening. Merci for the inspo

  • I actually love the Thursday look?!

  • Well done! I also bought a pair of boot cut jeans for the first time in years, and I have to say I didn’t hate them. 🙂

  • OMG this is amazing! I went through a belting-everything-at-the-waist phase too! I distinctly remember wearing leggings, and long loose or tight tank tops, often belted at the waist. WHY?!

    My basic style in the later years of senior school was leggings, usually patterned, and a t-shirt and hoody… that’s still my go-to outfit for weekends <3

    This post is so cute <3

  • Elizabeth

    Did anyone else go through a hardcore pseudo-Blair Waldorf phase somewhere around 2007-2009? Headbands, colored tights, babydoll dresses, monogrammed blazers, patent flats, holy shit, what was I thinking?

  • Verhanika

    Thursday and Friday outfits are fucking on point. I would wear these today proudly.

  • This looked so fun! My fave was definitely the “Coop” look, that girl could pull off polos and denim skirts! Now I’m gonna go look through some of my old outfits from high school and see what I can conjure up. Thanks for the inspo!

  • I had a uniform and it was pre-facebook so I thankfully have no evidence of it happening. I joked for years I’d wear the full uniform to the 10 year reunion, which I skipped. Its all probably for the best.

  • Katy

    My freshman year uniform vacillated between a) Old Navy denim mini, brightly colored American Apparel tights, some sort of top (probably from Justice), and Converse or my beloved slouchy black boots with a rhinestone piece sign and b) Old Navy bootcut jeans (black or blue with rips), a tee, a vest (black Lucky Brand waistcoat or an argyle Forever 21 sweatervest) and sometimes, yes, a fedora. Always tons of bright and cheap jewelry. It was 2009, people.
    My style got better through the years and by senior year I was wearing clothes I would wear now. I love laughing at what I wore at the beginning of high school, but that crazy phase was an important step in developing my now tastefully (I think) bold style.

    • Harling Ross

      A fedora!!!!!! That’s amazing

      • Katy

        I once wore said fedora with a white button down, tailored black shorts, teal tights, plaid converse, and black suspenders. I had never been more proud of an outfit. A substitute teacher told me my outfit reminded him of “A Clockwork Orange.” Only in hindsight did this comment creep me out.

  • Natasha

    A few weeks ago there were posts going around Facebook with people sharing their first ever profile pic. “Oh, that might be fun!” I thought. Checked what the pic was – nope, it’s just too 2007, I couldn’t do it. https://uploads.disquscdn.com/images/42ccf34a1e57f016f46597c38ab981009b69df79607664ec16b358660e28f09c.jpg

    • A Local Honey

      that is a LEWK

  • Ciccollina

    Omg BELTING. I remember belting! Jesus.

  • Kate Seward Chambers

    Loved it, but it would be great to see it recreated by someone who went to school before 2006 🤔

  • lateshift


  • Charlotte Gjedsted

    please bring boot cut jeans back, starting with that current outfit.

  • Amelia Diamond
  • Hansika Vijayaraghavan

    I’m abnormally small for a human being (I’m 5′ tall) and I’ve always been small but refused to shop in the children’s section so I’d buy the smallest, special-order size of jeans at Delia’s so I could shop at a teenager’s store while still wearing something meant for an 9 year old at 14. I now buy most of my pants in the boys section.

  • Pia Bergman

    In high school I was obsessed with wearing articles of clothing that were not clashing by happenstance, but I INTENTIONALLY paired clothing with opposing colors on the color wheel. This means: Pink (usually neon) with Green, Purple and Yellow etc. I was very into statement blazer/jackets. I had a neon green tweed Chanel-style jacket that I wore constantly, usually with bell bottom jeans, checked Van slip-ons and a printed tee. I also rocked a burgundy velvet blazer even through college.

    I agree with the belt-phase. I would put a belt ON TOP of a buttoned peacoat (worn with with tights, shorts and a felt hat obvi).

  • Tiffany

    Idk if should be embarrassed or upset that I still dress like I’m in high school and I’m 24 to make things worse I, currently wearing a Lacoste sweater as I write this

  • Jessica Simpson

    This article does not really live upto the information provided here – http://www.manrepeller.com/what-is-man-repeller .

  • stinevincent

    I think I’m a few years older than you, and remember that BELTZ summer (in my case, fall and winter, too) quite well. I’m actually slightly horrified at the prospect of the waist belt coming back in a big way. Not ready to repeat those looks.