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To speak of preppy-with-a-twist among trad purists is to garner reactions ranging from “What does this have to do with Ivy style?” to “Stop wasting my Internet, I want to look at old advertisements.”

But as much as Ivy stylers would like to forget it, the apparel industry does not operate within fixed genre parameters. There are gray areas, economic changes, and the ever-nebulous terminology used to describe things. It is hardly arguable, however, that fashion trends have at least some measurable effect on even the stodgiest of menswear merchants. From approximately 2004 to 2012, the fashion trend we can term “Neo-Prep” achieved remarkable mainstream popularity.

But will it last?

It may seem odd to attempt a history of less than a decade of a single fashion trend, but in the Information Age 10 years is an eternity. Some time at the dawn of the 21st century, this trend began possibly as a refutation of the relaxed nature of the ’90s, a rejection of the slovenly style of Silicon Valley, or a reaction against collegiate t-shirt culture (including those intrepid undergrads who wear flip-flops in January). Regardless of its origins, the aspirational wheels were in full motion by 2009.

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Gant, heyday shirtmaker for the Ivy League that has since evolved into a multinational European apparel brand, refocused much of its creative energies on its Rugger line designed with an eye towards ’60s Ivy League sportswear but cut aggressively slim and pre-weathered to appeal to the mass-marketed rebellious vibe embraced by millennials. Rugby Ralph Lauren, founded in 2004, was having remarkable success in branding itself as a “preppy with a twist” line for young adults anxious to set themselves apart from the masses by sporting a tie and a fake crest with their denim instead of an ironic t-shirt. The year 2009 was also the start of Tommy Hilfiger’s eventual resurrection from streetwear obscurity to preppy powerhouse. After years of logo saturation and brand trashing, the company slowly brought itself about. With giant steps forward, including a rejuvenated relationship with Macy’s and acquisition by Phillips Van-Heusen, in 2010 Women’s Wear Daily declared Tommy Hilfiger the “Master of Reinvention.”

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The Neo-Prep cultural moment seems to have reached its high-water mark from 2010 to 2011. Perhaps the most glaring example of the existence of this hipster fashion prep subset was 2010’s unlikely collaboration between J. Press and Urban Outfitters. Books published during these years included the re-released “Take Ivy”, “Hollywood and the Ivy League Look,” but more on point “Preppy: Cultivating Ivy Style” and Lisa Birnbach’s return to prepdom with “True Prep.” In the spring of 2011, Tommy Hilfiger’s namesake brand embarked on what was billed a “Prep World Tour,” setting up temporary shops in public spaces across the world’s capitals in miniature faux-New England cottages.


After some setbacks in various American locales, Rugby Ralph Lauren opened a store in London in the fall of 2011.  Neo-prep blogs, foremost among them Unabashedly Prep, reflected an active population of young adults interested in taking preppy staples and wearing them in ways that felt current, items of clothing that were steeped in heritage (not always fully appreciated or understood) worn alongside neon sneakers that would pass muster at any ecstasy-soaked Röyksopp (for the fogeys: a Norwegian electronic music duo) concert.

Speaking of music, the soundtrack to the Neo-Prep trend is inarguably Vampire Weekend. This group of Ivy Leaguers exploded on the music scene in 2007 and was downloaded immediately onto countless Neo-Prep iPhones to be blasted in the ZipCar whilst cruising towards Chatham on Route 6 or Sagaponack on the Montauk Highway. The bands first two albums are musically lighthearted with danceable, African-influenced rhythms, yet they also touch on very preppy problems, such as materialism and the WASP legacies of colonialism and sexual repression. There is also a song about vampires taking over Cape Cod, which is a less pressing preppy problem, but a catchy tune nonetheless.


It looked as though the second decade of the 21st century would continue to be dominated by twentysomethings listening to loud music in louder clothing, yet in 2013 Rugby was shuttered. The void was filled by the confusing Red Fleece line by Brooks Brothers, and York Street by J Press, which is less Rugby and more Thom Browne-style fashion forward rather than tweedpunk lifestyle. The novelty of überlayering has, shall we say, worn thin, and Neo-Prep outfits look terribly dated to this author. Tommy Hilfiger has subdued some of his louder outfits, and  Ralph Lauren is making far more money from Denim & Supply grungewear than it ever did from Rugby. Vampire Weekend’s latest album, “Modern Vampires of the City,” released three years after their previous project, is darker, more concerned with recent college graduates’ chronic unemployment than Louis Vuitton or coastal escapades.

True preppy style — clothing that could be described as Ivy style weekend wear — isn’t going anywhere. It will continue to influence fashion designers, to be used as a cultural marker for wealth, to be worn by those across the globe who appreciate it. However, the highly specific youth-driven fashions sold for the past few years (velvet slippers worn as street shoes, fake varsity patches, tweed vests worn with bow ties and distressed denim) have largely either disappeared from current mainstream stores, been adopted as streetwear by adolescents, or been drafted piecemeal into higher-end fashion lines at higher prices. It would seem that Neo-Prep has, for the time being, disintegrated.


If this trend has indeed run out of steam, if the Neo-Prep zeitgeist has truly run its short course, ultimately what may have doomed the upbeat movement is the decidedly downbeat spirit of this new decade. The same anxiety that spawns countless nightmares of nuclear cannibal apocalypse and has replaced the stylish vampire with the decaying ravenous zombie in films does not bode well for fun shirts and Converse sneakers.

Considering that 2012 was only last year, it’s a little soon to attempt a post-mortem. After all, this may be a mere lull in what might turn out to be an enduring trend. It also remains to be seen where the bulk of the young people that drove this trend end up, sartorially speaking. It’s very likely that the generation will simply move on to the next trend, whatever that may be. This is the usual course. Naturally a few will stay on, to be found wandering the halls of the Ralph Lauren, catching the elevator at 346 Madison, or pestering the salesmen at J Press. — DANIEL C. GREENWOOD

Daniel Calvert Greenwood is an occasional writer, but can be found more often singing classical music professionally. His family owned and operated a textile company from 1865 to 2005 that paid for many Ivy League tuitions and many Brooks Brothers suits. He lives in New York City.