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Pondering Our Fates for Fun: Generation Z’s Neo Preppies

My mother was, and very much is, a preppy. In her Reagan-era adolescence, the United States was in an aspirational mode, but also fascinated with a certain ‘Old Money’ traditionalism. Growing up in rural Virginia, she was captivated by an idealized vision of the Upper East Coast: an aged Katharine Hepburn in a pair of broken-in chinos and a fishermen’s sweater hiking through the maples, John F. Kennedy Jr. and his flock of Kennedy cousins playing pick-up football in swim trunks in the dunes of Hyannisport. The aesthetic meant dressing as if one was bound for a hereditary place at an Ivy League or Seven Sisters college, evoking both a bright future and a storied past.

Generation Z’s Neo Preppies

There was no context for this ideal during my own youth. She tried, with only lukewarm success, to turn me onto the staple pieces of her preppy past, like argyle sweaters and Bermuda shorts. My generation flirted with 80s nostalgia, but in an insouciant, slash-and-burn manner that resulted in some best-forgotten fashion crimes of inattention to detail. Millennials didn’t look to the past in the way that 80s preppies did, nor did they enter adulthood with a secure vision of the future. As for the preppy ideal, of a litter of bright young things birthed from America’s blue bloods, the late 80s and 90s novels like the college thrill kill satire The Secret History by Donna Tartt, and Bret Easton Ellis’s decadently cynical and violent American Psycho exposed the underbelly of toxic entitlement and elitism beneath that dream. This Gothic strain of preppy prose employed plots littered with lurid crimes to address the character defects and vices of the upper classes and those who aspired to infiltrate them.

Gen Z has neither the idealism of my mother’s generation nor the insouciance of mine. Inattention to detail is not their problem, and they are savvy observers of the increasingly dystopian world around them, whose technological ease makes it second nature for them to create and distribute their reflections of, and rebellions against, that world.

Through social media, they have honed a new school of preppy. They thirst as hard as my mother and her peers ever did for tweed blazers and Montblanc ink pens, loafers with an actual penny in them, and the perfect cable knit sweater, airing their style through Pinterest, Instagram, and Tumblr posts. While a love of fashion brings neo-preppies to the digital forum, their aesthetic runs deep: rec lists of classic paintings to appreciate, novels with a studious and tragically romantic air to consume, and YouTube playlists of indie deep cuts and classical composers sat cheek by jowl, with titles such as, “Feeling Melancholic But Still Have to Study”, “You’re Studying in a Haunted Library With Ghosts”, and “Studying With Poets Long Gone.”

To those who call themselves “Dark Academics”, The Secret History isn’t a cheeky expose of American upper-class callousness, it’s a foundational tome. The neo-preppies are aware of, and embrace, the Gothic side of their orderly aesthetic, and are excited at the idea of ghosts, figurative and metaphorical, that could be lurking in old university libraries, museums, and mansions. They are inspired by the boarding schools of both “The Dead Poets Society” and Harry Potter alike and see no aspirational end in particular to their fantasies. Their orderly curation belies a dedicated and rebellious whimsy. These Gen Z neo-preppies have come into cognizance as hard truths and harder conversations about race and ethnicity and their accompanying systemic oppression, the course of the environment and climate change, and economic reform have bloomed around them, with no resolutions in sight. Their rebellion is to play in the trappings of the past, to befriend its ghosts with boldly playful courage and almost aggressive thoroughness, plus a voracious curiosity my mother’s generation had no inkling of and mine had no stomach for. They are intellectual enough to mourn the fate of Jay Gatsby and technologically adept enough to vlog about it, dressed in impeccable sweaters. They’re wide awake, at home in the ruins, and ironically wearing tweed while pondering all our fates, just for fun.

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