After having passed half my life adhering to the demands of a school uniform dress code, my feelings are mixed when it comes to the resurgence of prep school fashion.
When I was still attending double periods of math and had the luxury of a recess break, my relationship with the school uniform teetered between noncommittal acceptance and a hypervigilant fascination with the micro-trends of the locker room. Although I never questioned why I was required to wear a tie like an eleven-year-old investment banker, I was passionate about the length of my skirt. My main concern between the ages of 13 and 18 was how short I could roll my skirt. Despite the school administration's best efforts to make our skirts a more comprehensible length for existing in the world, my desperate desire to roll it yet shorter still took up a shocking amount of space in my brain.
I was very impressionable when the original Gossip Girl debuted in 2007. While I was still required to wear a uniform, I was mesmerised by Serena's blatant disregard for the regulations of the prep school aesthetic. However, I now embrace the no-frills button-up look of Constance and St Judes in my daily life. And with the 2019 HBO revival of the school uniform powerhouse, the preppy look has returned to the zeitgeist for a new generation.
I have noticed three typologies within the blazer and box pleat revival. Musician Olivia Rodrigo has spearheaded the first, a sort of school uniform with an early aughts rebellion interwoven. The second is a more vintage take on the prep school, influenced by the dark academic aesthetic, the recent resurgence of Princess Diana, and the plethora of biopics on the People's Princess. There is also a slightly more minimal and sportier version, with little tennis skirts and sweatshirts along the lines of fashion labels Sporty & Rich and Rowing Blazers.
However, the school uniform look frequently hovers slightly too close to some schoolgirl fantasy and ignores the full depth of the preppy tradition and look. It's borrowed from the boys, with boys including your grandfather's collection of tweed and cashmere, your financier uncle's striped shirts, there is perhaps some sportswear from a boyfriend that is into sailing, and most importantly, your 8-year-old cousin who is visiting from boarding school. It's every character from 'The Talent Mr Ripley' (1999)
Although often seen as strait-laced, the preppy look can veer into desperate chaos. As seen with Caroline Calloway's transition from Cambridge Art History graduate to the New York literature scene with a side-step into Rowing Blazer advertisements. There is a whole gamut of possibilities of tailored basics and sportswear that shifts and adapts to the occasion with a gentle ease, rather than the strictures of a dress code.
Although I no longer have a dress code, I have made my own which consists largely of shirts from my brothers' Nautica and Tommy Hilfiger days, white turtlenecks like a primary school winter uniform, and loafers, mainly because I can never muster up the effort to lace up shoes. I don't care how effortless Veja trainers look; the sheer effort of lacing up sneakers from bending down and unlacing them and then having to do it all again is just too much for 7:30 in the morning. To complete the look, I am still searching for the perfect grey pleat front trouser, and I may just have to return to the uniform swap shop at a local high school.
Despite the current expression of the prep-school look, the underlying tradition of prep fashion realises a desire to get dressed and have your clothes, from the articles themselves to the way you wear them, embody a certain leisurely vision of your life. It is wearing clothes with a certain ease, rather than easy clothes. More importantly, it is an ease within the clothing that allows your outfit to become secondary to your lifestyle. It is less school uniform and more those few hours when you got home from school and the late afternoon sun would settle through the windows and you hours to simply exist.
While I will continue my search for the ideal grey trouser, I truly desire those unhurried afternoons, with stiff shirts softening and no fear of what to wear tomorrow.
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