I have never been preppy. When I was growing up, being labeled a ‘prep’ was almost as bad as being referred to as a ‘poser’, i.e. the uncoolest thing that could happen to you.  I avoided being preppy at all costs. Much better to be an individual, punk, retro or unique, I thought.  And, for the most part, I still follow this basic rule.

However, there is just something about that preppy look. “Fashion is about how you want people perceive you,” a buddy of mine said the other day, “ and being preppy shows the world that you are pulled together, powerful and in control.” She explained. “That, or that you are rich.”

Growing up those are not necessarily the ways in which you want to be perceived. Much better to be cool, bohemian and show the world that you just don’t give a fuck. That’s what I always thought, anyway. However, as we grow up and enter the business world, perhaps we have something to gain from tapping into the inner preppy. I mean, are your collection of vintage concert t-shirts and Manic Panic streaks going to help you get hired or close a deal?

I have just returned from a weekend on Cape Cod, i.e. ground zero for preppy chic. And while I did not spot any Kennedys, I did see a few Puritans.

Puritan is a Cape Cod boutique that was founded in 1919. Walking into their Chatham location is like walking into a movie set. As soon as I entered, I drew in a breath of perfect, clean, crisp Americana. So this is Cape Cod style, I said aloud, pleased with myself for discovering such an authentic gem.

“There are actually 2 Cape Cod styles,” explained Michelle Wilson Blaze, the Manager of Puritan Chatham. “There are the people that are from here, and then there are the washashores.”

Inside the Puritan shop.

I love local terms for outsiders, but ‘washashores’ has to be my new favorite.

“The people from here are the really conservative kind of preppy, the brands they wear haven’t changed, and they tend to wear the local brands like Vineyard Vines.”

Washashores, it was explained, wash up on the shores of the Cape from places like Boston and New York, bringing with them a bit of their big city tastes along with preppy sensibilities. Brands like Tory Burch and Burberry pop up in the store, adding a contemporary preppy twist on the classics. Ginghams, tunics and embroidered tops peer out from among the plaid and Bermuda shorts.

For men, the style is pretty consistent. Blaze explained to me that the men wear Polo. The old men wear the small horses and the youngs wear the big horses. They all wear khakis and if they are over 50, well, then it’s time to bust out the Tommy Bahama.

Some of these preppies probably don’t realize how au courant they are.  The ‘it’ preppy shoe happens to coincide with the ‘it’ shoe of the rest of the world at the moment: the Sperry Top-Sider.

“We have women coming in here are snatching up all of the Sperry Top-Siders, because they just can’t find them in Manhattan,” Blaze explained. Sperry Top-siders are a preppy staple, and stores like Puritan have sold them for years, but now that they have exploded into the mainstream, they are flying off the shelves like never before. The Puritan Chatham location reports selling almost double the amount of Topsiders this year than previous years.

Behold the Topsider.

So are Topsiders just the tip of the preppy iceberg? Are we entering a new era of prep? Possibly. True Prep by Lisa Birnbach and Chip Kidd – the follow up to the 1980 classic book The Preppy Handbook – is set to be released in September. Maybe it will lure another generation into the cult of cashmere?

Fall is a great time for Blair Waldorf wannabes to break out the blazers, plaid skirts, knee socks and loafers. But the new preppy look, much like the beloved washashore style, comes from taking the preppy with a twist of funkiness and individualism. According to Style.com, the “The casual Preppy style trend 2010 would train you to look stylish and also unique”. They suggest taking classics and adding something unique to make it your own.

For some great tips for dressing preppy with a twist, I highly recommend the blog Preppy With a Twist. Its author Mariel is “caught somewhere between a prepster obsession with plaid and the hard hitting trends of New York.” Sounds perfect!

So I guess it’s time to grow up. Preppy sophistication doesn’t have to mean selling out. The new preppy is elegant, refined, and an individual. And that is something I can work with.