The Prep Year

Where the walls so tall and stately of our Alma Mater rise,

Where the elm trees’ waving fingers strive to touch the bending skiesNature smiles with aspect sweet—darkly braided on the greensward at our feetLie the shadows of the elms.

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It is both a blessing and curse that hindsight is twenty-twenty. On the one hand, it’s great to be able to reflect and see the missteps of your younger self, but on the other, it nags at you in such a way that you just know, if you could go back and do it again, you wouldn’t make such stupid decisions. I can pinpoint when I realized that who I had been for fourteen years just wouldn’t cut it anymore. I was walking through the King of Prussia mall with my mother when we stumbled upon a store that I had only heard about online; it was a quintessential maker of so many pieces in every New England prep’s wardrobe. Needless to say, I had never owned anything from that store. I didn’t beg, but I think she could see a sort of longing in my eyes, because she asked me then and there if I wanted to go inside.

Stepping into this store was a religious experience. For a moment, I was immersed in the culture of Augusts on the Vineyard and white-skirted tennis lessons and breaking in new boat shoes on an actual boat. It wasn’t unfamiliar to me—I had been surrounded with this since my private early childhood education—but somehow, this time, it felt different. Perhaps more attainable. I remember looking at a price tag of a garishly printed shift dress in a loud turquoise and seeing a number with three digits before the zeroes. If I could’ve reached out and grabbed in my hand that feeling of belonging to this exclusive society earlier, I certainly couldn’t now. My mother called me over to the clearance section. I have never been one to scoff at the clearance section; growing up poor, I couldn’t be. It was then that she showed me two items. One was a tote bag with bright pink straps. On the body were black pandas that looked like they had just been drawn on with a calligraphy pen. The other item was a kitschy knee length skirt with an all-over pink and orange bicycle print that looked more like an array of citrus fruits than anything else. I now know how ridiculously lurid these things were, but in the moment, all I knew was that this is what the girls I went to school with wore. I told my mother I loved them both, though in retrospect I might not have really loved them at all; I might’ve just seen them as a key to this insider world I so desperately longed to be a part of. Since they were on clearance, my mother told me I could have them, and I remember beaming with glee, feeling like she had just given me the world. The total was still too much money for one skirt and one bag, but I would be going into my freshman year of high school with girls I have known all my life and I’d be able to look like them—or at least to dress like them; their complexions were noticeably lighter than my own.

You don’t really realize how much you did to try and fit in until you get some distance. Now, at twenty-one, I wish I could bound back in time and tell my self-conscious fourteen-year-old self that the skirt won’t help me make any friends, that the bag won’t do more than hold my books. Neither the skirt nor the bag were much of a conversation piece, as I had almost expected them to be, but I don’t think I minded that. If no one was talking about what I was wearing, I assumed it meant I did a good job. I was your run-of-the-mill Moses Brown School girl, bicycle skirt, panda bag, and all. The difference was this; at the end of the day, I wouldn’t be going home to my Barrington waterfront mansion, playing with my two Bernese Mountain dogs in our gorgeous, sprawling front yard, waiting for mom to come home and cook us an organic dinner. I would come home to a section-eight apartment with a cat and a small dog we weren’t technically allowed to have, take off my skirt and take my books from my bag, and return to the real world.