While fashion scholars can debate all day long about the distinction between Preppy, Classic, and Traditional styles, (and, believe it or not, they actually do ) we kind of have to agree with the ones who claim that what people call Preppy today isn’t what it used to be. 

Before it was co-opted as a “look” by the mainstream in the early 80’s, it was generally acknowledged that the prep-and ivy-educated elite (and those who associated with them), tended to favor a sort of dorky, dowdy, uniform look that consisted of certain well-made, classic sportswear pieces and, for the men, boxy English-style suits.   The “uniform” (khakis, polos, crewneck sweaters, etc.) was consistent and more or less the same for everyone, regardless of age or gender, which is why, as Lisa Birnbach put it in The Official Preppy Handbook, “Preppies wear clothes for twenty-five years and no one can tell the difference."  
And while that sounds lovely now, it should be pointed out that in the 1960’s and early 70’s, when most young people were wearing things like bell-bottoms denim jackets with peace signs on them, dressing like one’s grandparents was not exactly the quickest route to Cool Town, if you get our drift.  No wonder preppies rarely left their private Clubs--they would probably have been beaten up anywhere else.  
(Which is why it was such a big deal when Oliver Barrett IV went outside the tribe and married Jennifer Cavelleri in Love Story--didn’t he get beaten up by townies or something at one point?)  

But then 1980 arrived, and it was suddenly Hip to be Square, and The Preppy/Preppie look became all the rage (much, we’re sure, the the Old-School Preppies’ horror).  Whether it was the new Reagan-era political conservatism, a pop-culture obsessed with 50’s nostalgia (Happy Days had been a TV hit for years, and Grease was one of 1978’s top grossing movies), or a simple case of hippie-disco backlash is anyone’s guess, but America’s youth abandoned their platform shoes and tie-dyed shirts en masse to start dressing like Ward and June Cleaver.

Of course, that meant that a lot of the tenets of true Preppy
dressing were compromised (which, any Preppy can tell you, always happens once you let the
riffraff on board). 
Mass-produced Fair Isle sweaters were blended with--gasp!-- acrylic, non-Topsider boat shoes that wouldn’t make it across a swimming pool deck flooded the stores, and there was a waiting list--waiting list! for an L.L. Bean down vest.
Alas, poseurs and wannabes were everywhere, forcing the genuine Preppies, like poor Louis Winthorpe III, even further underground.

While some good did come out of the whole thing--Lilly Pulitzer revived her defunct brand, and La Coste Chemise regained it’s licensing rights back from Izod, for instance--there are lots of
young people out there who, to this day, think of Preppy as nothing
more than an 80’s fad, like Punk or New Wave.

That’s certainly not the case--trust us, Preppy is alive and well
and living in colonized pockets across the country--but we do feel like there’s a broader definition these days.

To us, the new Preppy is not a person, but rather a taste point that tends to attract a broader range of upper middle class people who, while they might not have prepped in the East or attended an Ivy, were most likely educated in private schools and/or colleges. (That’s not a prerequisite, by the way--just an observation). But now that merit-based admissions are a reality at even the most exclusive prep schools, today’s well-heeled elite is much more assimilated with mainstream culture, and as a result, more influenced by fashion-- than they used to be.  And while it’s hard to shake those Prep roots once they’ve been hardwired, (in our case, it was a result of growing up in one of Connecticut’s WASPier towns ) most of us have moved beyond the old boundaries.
In short, we would define today’s Preppy as simply a look that combines traditional elements and quality workmanship with current trends.

So what’s Preppy now? 



Of course, the old standbys, La Coste, Lilly, and Lauren—are still
going strong, especially because they all continue to tweak their
iconic pieces (adding stretch, changing the silhouette, etc) to stay
current.  (Unfortunately, not all of yesterday’s preppy favorites have kept up--you won’t find many well-dressed people under 45 shopping at Land’s End, Talbots, Brooks Brothers, or even--we hate to say it--Ann Taylor these days.)


But lots of other favorites have endured :  Yankees love Thomas Pink, J.McLaughlin, and Vinyard Vines,  Southerners still wear Vera Bradley and Jack Rodgers, and the Palm Beach crowd continues to go for Molly b and Charlotte Kellogg.

And the purists can deride J.Crew all day long, but there’s no question that this retailer embodies all of the beloved hallmarks of young Preps everywhere while still managing to be hip.  (In fact, if you want an Official Preppy Handbook for 2008, just pick up a current J.Crew catalog.)  And if you haven’t noticed, Banana Republic is looking more J. Crew-like every day.

 As far as Ready-To-Wear designers and up-market retail lines go, the current favorites are definitely Tory Burch, Theory, Marc By Marc Jacobs, Diane Von Furstenberg and Kate Spade. 

Tory Burch Reva Flats

And for a uniquely Tampa take on Preppy, don’t forget  Town Toiles and Nilla Shields

Tampa Toile Tote from Town Toiles

Because remember, old Preppies never really die....

...they just leave office.