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Preppy 2.0
Preppy 2.0

A guide to navigating this brave new world of genderlessbathrooms and Ivy League wannabes with your tartan intact.

Alex Hawgood

It’s not easy being a card-carrying Prepster in 2018. The tennis club now has genderless bathrooms, New York University practically acts like it’s part of the Ivy League, and, last October, J. Crew founder Arthur Cinader, one of the last great preppy-style deities, was finally bumped off the waiting list for that great country club in the sky. Don’t bother dusting off Lisa Birnbach’s Official Preppy Handbook, either. Published almost four decades ago, this book of once timeless how-to’s is, sad to say, about as relevant today as a black velvet foulard bow tie. So how, pray tell, is the modern Prep supposed to navigate these topsy-turvy times? Well, fair reader, you are in luck, because we here at W are going to help you figure it all out.

While we cannot offer guidance about whether the labradoodle, the sheepadoodle, or the bernedoodle is the right hypoallergenic pet for the modern preppy household, we can happily dispense our seasoned expertise on something far more urgent: updating the preppy dress code for 2018. Whether it’s Demna Gvasalia’s subversive CBGB spin on Connecticut boarding-school attire at Balenciaga, or Miuccia Prada dipping into fox-hunting drag at Miu Miu, looking the part no longer means sticking to the fuddy-duddy cult of forest greens and salmon pinks. (Unless, of course, you aspire to look like an off-duty Republican senator.) If you follow the abundance of wisdom on these pages, you’ll be able to hop from a sailing trip with the boys along the Sound to superyacht adventures with Russian oligarchs in Ibiza, from an AA meeting to a green-juice bar, from J. Press to Dover Street Market without a hiccup.

Post-Nuclear-Meltdown Prep

In today’s uncertain world, you might, on occasion, have to dress for life after a nuclear blast. It’s in the Prep’s DNA to overcome trying conditions: Just as your ancestors endured the Mayflower’s spartan amenities, you should be able to withstand fire and radiation equal to approximately 10 million tons of TNT. In the unfortunate instance that nearly everything and everyone else turns to toast, it’s wholly appropriate to take refuge in the most quintessentially preppy emblem: plaid. Should garments in your family clan’s heritage check be incinerated, an appropriate backup is Alexander McQueen’s Mad Max spin on the über preppy shirtdress, paired with a thin black belt with a shell clasp. (As every preppy woman knows, garments are to disguise rather than emphasize the female form.) The look was shown with motorcycle boots, which, with their low, stacked heel, are useful for stepping over radioactive puddles.

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Best Performances Volume 1 2018