Trucker Hat, Meet Boat Shoe: Here Comes the Prepster

In style blogs and magazines, newspapers and television shows, fashionistas have recently begun bandying about a new term: prepster. An amalgamation of two seemingly irreconcilable looks, preppie and hipster, the new style seems poised to take hipsters to a new sartorial level while it brings preppies to the forefront of fashion.

The new look draws much of its inspiration from preppy clothes, a style that, while seemingly eternal, is somewhat anti-fashion. With its emphasis on classic looks, loose-fitting clothes and well-worn garments, the preppy ethos evokes a style that is never really in fashion, but also never completely out of fashion. It seems to promise that, while tweed jackets and pink shirts may never fit in with club wear, they will serve the wearer well in most circumstances.

On the Margins: Preppy Style

The preppy style's classic retailers are similarly stodgy and reliable. In 1980, Lisa Birnbach's The Official Preppy Handbook outlined the classic preppy brands, a collection of companies that have never really achieved fashion superstardom, but have managed to maintain a robust cultural presence for decades -- or, in the case of Brooks Brothers, over a century. From LL Bean to J Press, Murray's Toggery Shop to Paul Stuart, these brands are the opposite of faddish: steadily profitable, they have generated loyal, if relatively small, followings.

After Birnbach's book was published, the preppy look gained greater cultural traction. Mass-market brands began taking the style to a broader audience: Ralph Lauren (RL) and Abercrombie and Fitch (ANF), for example, took preppy to the mall, wooing millions of consumers. On another level, Land's End, a classic preppy company, sold out to Sears (SHLD), vastly widening the scope of its audience. Yet even with Land's End and Lauren courting the masses, the preppy look never really attained the cutting edge of culture.

The Hipster Cachet

For the past ten years or so, that cutting edge has partially been occupied by hipsters, a loose conglomeration of young urban style mavens. Pinning down the hipsters is extremely difficult, although writer Mark Greif attempted that feat in the most recent issue of New York magazine. In his article, Greif proclaimed the death of the hipster, noting that its growing broad base of popularity is poised to ruin the mystery and exclusiveness that has given the style much of its cachet.

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Part of the problem with classifying hipsters, not to mention writing their eulogy, is that there is very little to unify the group across time and space. In their short history, hipsters have embraced a wide variety of styles, many of which are contradictory. Through it all, however, two key aspects have united the culture: an appreciation of authenticity -- the sense that a style has a strong, true cultural base -- and a deep vein of irony. Beyond that, hipsters tend to hew closely to American styles and products, and many of the products that they have fetishized have been middle and lower class American artifacts.

In their current incarnation, hipsters have leaned toward body-hugging clothing, like skinny jeans, form-fitting t-shirts, and leggings. The look's most iconic brand may be American Apparel (APP), whose collection of inexpensive lace and leotards propelled owner Dov Charney to the top of the hipster heap. Recently, however, Charney's ship has been sinking: APP's stock price is down from a height of $16.80 in December 2007 to a current rate of $1.05.

Charney's solution is to go preppy. In a recent interview with the San Francisco Chronicle, he said that "Hipster is over," and unveiled plans to move into blazers, button-down shirts and other preppy stalwarts. The revelation shocked many fashion watchers, who found it hard to integrate the old American Apparel with this bold new direction. However, for those who are familiar with popular brands Zara, H&M and Uniqlo, Charney's move shouldn't be too shocking. As DailyFinancenoted over a year ago, classically-styled, bargain-priced office wear is a booming market.

Embracing the Prep(ster)

While Charney's move to prepster style may be a tipping-point of sorts, he is far from the first retailer to embrace the look. While popular retailers like the aforementioned Zara, H&M and Uniqlo have latched on to a stylish office look that borders on preppy, some of the classic preppy brands have also sought to capture the hipster market. LL Bean, for example, launched LL Bean Signature, a more slim-cut, tailored version of the company's classic garments. Priced a little bit higher than most of the brand's offerings, Signature's clothes were designed by popular designer Alex Carleton, and are skewed to a younger audience. Similarly, Brooks Brothers' Black Fleece and Paul Stuart's Phineas Cole lines also pander to a more body-conscious audience.

As with any emergent style, it remains to be seen if the prepster look is the fashion of the future or a flash in the pan. However, its ability to draw from two distinct, well-established subcultures suggests a promising outlook. With cultural analysts and fashion critics arguing over whether prepsters are groundbreaking hipsters or hip-leaning preppies, it seems like the style may actually be a robust mix of two strong styles that work well together.