Nantucket Reds, Sperry Top-Siders, Brooks Brothers shirts and knit v-neck tennis sweaters delicately draped over the shoulders have been the traditional garb of the Northeastern elite who spend their weekends dividing time between regattas and country clubs. More recently however, “prep fashion” has started to permeate into sartorial spheres outside of the yacht club, faring on a more prominent level than in years past.

Books such as Shosuke Ishizu’s 1965 fashion book, “Take Ivy,” and “The Official Preppy Handbook” are gaining popularity with their recently released sequels and reissues. Former prep mainstay Abercrombie & Fitch is returning to its roots with the release of a new collection, Elements of Ivy. The collection features a varsity cardigan, sweaters and not one, but two different khaki chinos, just in case you want to mix it up.

Most notably, hipsters have taken notice and have co-opted the trend in a paradoxical manner — just as most suburbanites cannot understand the emotional terror of brutal gang violence, most hipsters know nothing of boat races on the lake and tennis matches at the club. Retailers like Abercrombie, Hollister and American Eagle Outfitters are actually considered “poor people” brands by the Ivy League style crowd.

The term hipster itself also carries several meanings. The hipsters referred to here aren’t people with a slight interest in fashion and music that extends beyond the realm of radio, but the self-proclaimed cultured elite, who make obscenely large differentiations from normative social and fashion codes. Trying to be hip is fine. Trying to be the epitome of hip is obnoxious.

Mark McNairy, former creative director of prep-wear mainstay J. Press and perhaps the human manifestation of the mesh between hipsterdom and preppy, noted the clientele shift within Ivy League-inspired fashion.

“When I started [at J. Press], basically their customers were dying … literally. Most of their main customers were in their 60s or 70s,” he said in a 2010 interview with New York Magazine. “The young customers we have now are, like, really hip kids,” McNairy said in a 2007 New York Times article. American Apparel has further demonstrated this trend, “diving into more sophisticated garments such as blazers, pleated pants, shirts and more formal lace tops,” according to BusinessWeek, as opposed to their more stereotypical hipster clothing offerings.

Dov Charney, CEO of American Apparel, expounded on the movement from hipster to prepster in an August 2010 interview with a blog on Village Voice. “The stereotype of a hipster is not something people aspire to anymore. Nobody wants to be a hipster.” If you are at all skeptical of Charney’s observation, look no further than American Apparel’s share price, which is hovering at under a dollar after having been removed from the New York Stock Exchange. The stock underwent a 66 percent loss in share prices over the previous year.

Charney’s keen analysis of his company’s own shortcomings are about the only legitimate piece of insight he offers, as he claims later in the interview that neon has the potential to become preppy and the idea of American Apparel being predominantly hipsters as more of a perception than a fact. Charney will probably have a hard time navigating his way into a market that hasn’t changed in the past half-decade if he thinks neon will fly. As far as perceptions go, hipsters being American Apparel’s base consumers is indeed a perception. A perception of fact. People generally do not wear yellow unitards with high-waisted pants and horn-rimmed glasses with non-prescription lens.

McNairy is no better. In an interview with New York Magazine, he talked about his ascent from being a huge shopper to someone who just shops at the Salvation Army, where he apparently has built up a collection of over 300 Brooks Brothers button-down shirts. According to the interview, he also never leaves the house without his Parker Jotter pens, because heaven knows Pilot V7s aren’t obscure enough.

Since his departure from J. Press, McNairy has created his own personal line of clothes of exceedingly hipster design. Not because it is that cool, but because it is that bad. He even went so far as to release a T-shirt and handkerchief emblazoned with the phrase “Forget Ivy.” For the extremely bitter, and more bold, he has one that says, “Fuck Ivy.” Take that, Martha’s Vineyard!

The only people that have actually appreciated the clothing are the preppy Ivy Leaguers themselves. The popular prep-wear blog Ivy-Style.com featured the “Forget Ivy” handkerchief with the caption, “For the last couple of years, one of the recurring refrains on the trad forums and blogs has been an impatient wish for the Preppy/Ivy/Trad/Americana (PITA) trend to go away so that stubborn fuddy-duddies can go back to being behind the times. Rejoice, gentlemen, for that day is here: Mark McNairy, arguably the leading guru of ‘Take Ivy’ fashion hipness, has decreed the Ivy trend officially over on this $12 handkerchief.”

Prepsters’ hostility can’t be blamed. The entire mentality of hipsterdom is based on an illogical conundrum: being cool by liking uncool things. Under normative hipster principles, the more really bad things you like, the higher your status. By this logic, hipsters liking prep-wear means that prep-wear is really lame. Nobody who’s not a hipster wants to be lame.

Printed on Wednesday, August 31, 2011 as: Hipster fashion left in 2007, prep clothes make comeback.