A Question of Preppiness

I'll probably catch flak for this. I am well aware. Disclaimer: I am not hating on prepsters, but rather questioning the lifestyle that "preppy" sometimes puts forth. My big question is this one: why is the preppy clothing style also a lifestyle? Perhaps I just don't understand. Perhaps the way a "preppy" lifestyle is often portrayed as one that has too much money and seemingly people that care too much about material things, what label is on your collared shirt instead of whether or not someone is a good person. Don't get me wrong, I think the way someone dresses says a lot about who they are, and I also think it's important to adhere to the old cliche, "dress for success," but "preppy" takes this to an entirely different level.

Let's start in the beginning. I was raised in probably the least preppy town in Massachusetts. My best friend from high school was teased (playfully!) about her popped collared Polo shirts (she happened have an after school job at Ralph Lauren). I was publicly educated. My favorite store in elementary school was The Children's Place. Later, The Gap, or Express. I had barely ever heard of Lilly Pulitzer or Polo. "Preppy" didn't exist at my high school. I was an athelete, and most days my senior year I arrived 5 minutes late for homeroom with wet hair and clad in sweatpants. And I was not the only one that did this. Of course, it did matter if you looked good, but not to the extent of the label-whoredom of many "preppy" schools. Where I went to school, you were cool if you had a boy's football hoodie (cut down the neck of course). The older your car, the more notoriety. If you had a new car, you were spoiled. My sister and I were the only girls in school that had Vineyard Vines totes, and we only had them because we bought them one year vacationing on the Vineyard because we thought they were pretty (and for the record, that was 2004, and I still carry the same one).

So forgive me for not understanding. Recently, The New York Times wrote an article about the sequel to 'The Official Preppy Handbook,' a book that was written to poke fun at the preppy lifestyle but instead apparently backfired and taught everyone how to be preppy. Sweet. What really gets me is that it seems that preppies think that their way of living is the only way to live. Conveniently, there are a few prerequisites I have observed: One must have money, be a Republican, and apparently love monograms, Lilly Pulitzer, bowties and boatshoes. One must not only love these things, but tell everyone how much they love these things, and how much of these things they have.

Don't get me wrong. I'm not saying it's bad to like preppy clothing. In fact, despite my love for sweatpants, my style from high school has changed into a more classic, more preppy one. This could be a factor of where I decided to attend college, or it could simply be a factor of growing up. But notice I said style. Many of my friends adopt this clothing style without the lifestyle. I, too, have a decided appreciation for boat shoes and Lilly Pulitzer, but my closet doesn't vomit these things, and I would never look down my nose at people who didn't adhere to preppy clothing. What I'm trying to assert is that what has come forth as a preppy lifestyle is seemingly shallow: care only about material wealth and what one can buy with that material wealth, including the most expensive simple clothing there is, and then seemingly brag about it. Somehow, preppy clothing has translated into this preppy lifestyle, this way of living that shows the world how wealthy you are. My mother did not subscribe to a preppy lifestyle whatsoever, and yet always looked beautiful and put together and kept a beautiful home. If all you have is your monogrammed sweater to help you sleep at night, your life is empty.