Getting kicked out of a noise show isn’t the easiest thing to pull off: they’re usually hot, dark and the decibel level will likely come back to haunt your hearing. Yet not only does the artist Dick Carroll remember that he got booted from seeing the band Lightning Bolt seven years ago for trying to defend people from over-aggressive bouncers, but he recalls exactly what he was wearing: “A pink short sleeve OCBD, khakis, white socks and burgundy penny loafers.” He also mentions that his hair may have been “tidy” as well. He was a preppy in the pit with the punks. This was, in its own way, punk: “It was sort of counter-culture for me in the 2010s to dress this way.” That might give you pause, considering loafers and a Brooks Brothers Oxford shirt don’t exactly give off “smash the system” vibes. Preppy doesn’t sound like a style that goes against the mainstream. In fact, it seems like the opposite. But that really isn’t the case.
Today, the Australian-born Carroll has amassed a sizable fansbase for his playful drawings of folks wearing items like camel coats, berets or old oxford shirts. But the thing I especially like about his art is the untidiness of it all. His well-dressed subjects have messy hair, and mustaches, and a general lack of preoccupation. Between Carroll’s own noise show vibe and his work, he’s a perfect example of what I think of as the dirtbag preppy look, if you will. It’s Ivy, but for everybody. It’s Dirtbag Ivy.
To my mind, Dirtbag Ivy is a nod to the past, but one that is more Mad magazine and less secondary character in Dead Poets Society. The idea isn’t to look like you just got back from a country club or you’re the missing member of the Tenenbaums; instead, the dirtbag preppy look takes little bits from the past as a starting point, and lets the individual build from there. Think: t-shirt, jeans and a dad hat, but with a three-button blazer. Think: a striped blazer and schoolboy shorts with a pair of socks that almost go up past the ankles. Think: a renewed appreciation for the bengal stripe by the company that made it famous. There is the return of the beret. You can even wear a tie, but only if you technically don’t have to.
Tweaking the preppy look shouldn’t seem too radical, but it sort of goes against everything preppy fashion is and means. “Preppy” started out as a WASP subculture, an anti-fashion that developed among blue-blooded college students along the East Coast. The “look,” as Jeffrey Banks and Doria De La Chapelle describe in the book Preppy, developed in the 1920s as “a relaxed new way for collegians to dress by co-opting athletic clothes from playing fields, mixing them with genteel classics” and adding little bits of flair like ties or pins. And it mostly stayed that until 1980 when the perfect storm of satire and commerce struck. Ralph Lauren, Lacoste and other brands brought the looks to the masses, and in The Official Preppy Handbook, Lisa Birnbach was satirizing it, making it easier to understand if you weren’t part of the world the look and vibe originated from. The “guide” that explained things like the books every preppy needed to read (from The Catcher in the Rye to The Prime of Miss Jean Brodie by Muriel Spark and anything by George Plimpton) to the bars preppies hung out at to how “The Old Boy Network” supposedly works. It was supposed to be silly, but people took the satire seriously enough to make the book a massive bestseller, like they were getting a real look at a world that was once closed off to most of us. It was the first of many preppy waves over the last 40 years, but it nonetheless missed the point that, at its core, preppy was about rebellion. It was rebelling against the old-money, old-power old ways that students came from, which wasn’t exactly bolsheviks throwing bombs, but it was rebellion nonetheless. It was supposed to be fun. But somewhere along the way, “Preppy”—or its closely related cousin “Ivy Style”—started to mean dressing like you have power, or you’d like to have it. Subversiveness was mostly lost in translation.