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.

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 DailyFinance noted 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.

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Interesting article. I live in San Francisco, the land of insufferable yuppies and insufferable hipsters. What a weird combination of youngin's. That being said, as a hippie from my youth in the 60's (I am 58), I would actively challenge "J"'s comment that hipsters do not like authenticity. I cannot speak for youth of today, but I most certainly sought authenticity as a hippie in my youth. We were reacting to what we perceived as deadening corporate culture and we roamed through thrift shops and pursued crafts and creative work to make a different look than our parents had worn. I am still not corporate in any way and I live as a self employed person. Vinnie, I think your take on the Tea Parties is rather broad. I am not a Democrat, not a Republican, I am an Independent. I have no naive illusions that the government monster is going to stand down without a fight. However, in towns around our nation, there are people who are networking and helping one another and encouraging self-reliance. That to me is the essence of the Tea Parties: not a party per-se, but a realization that the core values that founded this nation are taking care of one another and not trusting in government to do it for you. I do not expect Social Security or Medicare to be there for me, even if I make it to 62 or 65. I paid into it all my life but I do not trust anything but my faith in God, which has sustained me. I dress in comfort and I am about as authentic as you can get,thank you very much.

November 01 2010 at 3:52 AM Report abuse rate up rate down Reply

ANYTHING is better than seeing those young men with the waist of their jeans at about mid-thigh with their underwear exposed. ANd those stupid baseball hats they were at a bill pointed sort of side tilt but not they REALLY think that look is attractive? If so, I've got news for them. Seems, the sloppier the wonder public opinions are low of them. OR exposed Butts. I DO NOT WANT TO SEE anyone's crack, thank you very much. To quote Bill Cosby, "PULL YOUR PANTS UP!"

November 01 2010 at 12:11 AM Report abuse rate up rate down Reply

pretty mumbley convo. Reaks of the emporer's new clothes

October 31 2010 at 11:07 PM Report abuse rate up rate down Reply

Your appearance reflects how you want the world to see you. Enough said.

October 31 2010 at 9:27 PM Report abuse +2 rate up rate down Reply

"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." No. Hipsters HATE authenticity. The entire point of being a hipster is to sneer at people who are authentically interested in something and express that interest. Hipsters pretend to be cooler than the world and to have rejected it. This is so they don't have to admit that it rejected them.

October 31 2010 at 7:16 PM Report abuse rate up rate down Reply

i like prepsters, they crunch nicely

October 31 2010 at 5:18 PM Report abuse +1 rate up rate down Reply
Big Bobzilla

Hey, the "Bum" look is just catching on. Unpressed pants, shirt you slept in, three-day growth of beard, unkempt hair. Don't believe me? Watch prime TV and the Late Shows. If people don't take pride in their appearance, they will have no pride in anything else. Including their country.

October 31 2010 at 1:17 PM Report abuse +6 rate up rate down Reply
1 reply to Big Bobzilla's comment

........round awhile in our yuppie_doms as they live out their grunge years..

October 31 2010 at 7:58 PM Report abuse rate up rate down Reply

Another 'space filler' chapter from AOL. Totally useless and senseless 'information' just to fill vacant space like the 'news' from the cable companies that is total garbage. I have cancelled my Comcast cable because of the number of commercials and will never go back to cable unless THEY PAY ME to watch. Passivity is a negative American trait that has brought us corporate ownership of our government, both federal and local. We should have the passion of the French who will not be cowed by their government into passively accepting the political dogma that is more in keeping with a dictatorship than a democracy. The TEA party defends the 'free market' that in turn controls their lives by bribery and corruption of the so called 'leadership' of their own political lives. To believe that corporations and people like Dick Armey have no agenda for raising millions for the TEA party is in my mind unbelievable and infantile. The TEA party WILL be brought under the total control of the Republican party regardless of what the members believe will happen. People like O'Donnel, Angle, etc, and the other neophytes will be eaten alive by the Republican party and to believe otherwise is very naive indeed. Parading home made placards and banners will NOT change the apathy of the majority of Americans. The world no longer looks to America as a 'leader' in anything so we should be prepared to do what it takes to make our lives better, because if we go down the tube, most countries will say 'good riddance' and keep moving on.

October 31 2010 at 1:12 PM Report abuse +1 rate up rate down Reply