Tom Cruise in Risky Business, 1983.Warner Bros / Getty Images
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.
Essential Dirtbag Prep: Jack in Carnal Knowledge.
But the fun has found its way back. As one of the originators of preppy style. J. Press might seem one of the least likely champions of this emerging sensibility. The brand was founded in New Haven in 1902 by immigrant Jacobi Press, who aimed to clothe Yale’s up and coming crop of America’s future leaders. Recently, though, the brand has started leaning into more contemporary looks like baggy jeans and a denim shirt with a blazer thrown over it and an embrace of the rugby shirt, a staple of east coast campus life for decades. That might not sound like anything too crazy, but if you’ve been paying attention to the Ivy Style culture for the last decade or so, you know that, for whatever reason, denim is looked down upon in that world. Things are changing; things have changed.
When I need inspiration, I look to the Instagram account @Berkley_Breathes, run by unofficial menswear historian Jonathan Wertheim. His motto—“I believe that Ivy is for everyone 🤝 Have fun with it -- it ain't that serious!”—sums up where the preppy look should have been going all along. In one post, dissecting the looks of one character from the 1997 film Contact, Wertheim points out that “Ivy style is fascinated by views of its clothing from ‘the outside.’" Which is to say that the whole Ivy-preppy look has long reinforced the idea of the insider. Wertheim is more interested in old pictures of Elaine May in her 1971 classic A New Leaf, or bald gentlemen in Shaggy Dog sweaters. He sees the history of the Ivy look along two lines. The first, is the WASP line: “This line continues into films and books about that culture, the Official Preppy Handbook, Kennedy idol-worship, and other general valorization of elite class culture,” Wertheim says. The other is “the underrepresented Ivy history—people of color, Jews, LGBT+, working class/blue collar, etc.”
Wertheim sees his place at the intersection of those lines. He doesn’t believe the history is false, “but rather oversimplified.” But Wertheim also believes that the idea of the death of formality has been greatly exaggerated—not because people don’t want to wear suits or ties anymore, but because “we’re tired of Men’s Wearhouse, car salesman versions of workplace formality, one size fits all shiny ties, bad shirts and black pants.” He points to the success of brands like Noah and Aimé Leon Dore who he sees “selling individuality, with a mix of formal and casual.”
The latest preppy comeback isn’t exactly new. It has been in the works for a few years now, with nearly every outlet that covers style recognizing the way brands like Rowing Blazers or Noah mesh old traditional prep looks with streetwear cool. To my mind, Dirtbag Ivy is something a little different, and that says something more about right now than the last few years. Dirtbag Ivy emerges from our desire to get dressed again—but not too dressed, at least just yet, maybe not ever. Dressed down dress up, basically. This might be a signal of how we get dressed in the future. We’ll likely still see people wearing blazers, but it’s just as likely there will be a sweatshirt or rugby shirt under it as there could be a shirt and tie. The old ways might finally be dead.
Personally, I couldn’t be happier about it. My own look is still largely based on my teenage years growing up a very not-WASP-y skateboarder in a WASP-y place when skateboarding wasn’t as socially acceptable as it is today. I always sat somewhere between trying to not draw attention and also subverting preppy looks: old Ralph Lauren Polo shirts I inherited and baggy chinos; a tennis sweater and jeans with a pair of Vans; a pair of old madras pants I cut into shorts; Brooks Brothers’ button-downs that I could purchase for a couple of dollars at thrift stores that I could wear while riding by skateboard along the curb at a bank before it opened, and then to school. I haven’t been on a board in years and would probably break a bone if I tried it, but my general day to day look is still along those lines. So, when the new Noah lookbook drops, I always find myself drawn to it, I understand where they’re coming from. And while I appreciate suits and ties, I’ve just never seen myself as a person who could wear those things on a regular basis. Something like a rugby and chinos with a pair of New Balance and a Barbour trench is my sweet spot. Or maybe a riff on Dustin Hoffman’s Kramer vs. Kramer look: a pair of corduroy pants, an old olive army jacket and a pair of loafers. And if I have to wear a blazer, personally, I’d rather wear it with a pair of jeans. Sorry. I’m always going for a little prep school, a little dirt bag; a little class and a severe lack of it at the same time.
Pay attention long enough and you’ll notice that the preppy look goes in and out. There’s a new take on it every decade. Yet this time feels...different. It’s less dependent on the ties to the old-school it had been sold on in the past. Nobody wants to look like they hang out with people named Muffy and Biff; nobody wants to suddenly start putting on the trousers and dress shirts that were already an uncomfortable fit less than 20 months ago. But none of us really know what the future holds, either. We’re slowly re-entering the world and the old rules don’t apply anymore. And while there’s something terrifying about the unknown, it’s also a chance to write some new laws and dirtbag some classic styles up a little.
-"Ivy Style Enters Its Dirtbag Era"