Did Anyone Else Have a Preppy Phase? What the Hell Was That All About?
Like most young adults, I cringe when I think back on some of the outfits I wore as a teenager. Instead of looking back on outfits full of bad trends or something from a long dead subculture, I have pictures of my 15 year old self looking like a PTA mom. It’s true. I walked into public high school each day looking like it was a casual Friday at my corporate office job. I had a preppy phase, and that comes with a whole different kind of embarrassment. Especially because I did not have the kind of money to actually pull it off. There was actually a lot that was embarrassing about it. Let’s unpack this.
My preppy phase started towards the end of middle school. I spent through the end of 7th grade desperately trying to fit in. My sense of style was just like everyone else’s at the time. I wore skinny jeans, Aeropostale t-shirts, and I styled my hair with a mini snooki bump. At school dances I would put some black pencil eyeliner that I dug out of my mom’s makeup drawer on my lower lash line. It was quite a time to be a tween.
By eighth grade I had figured out that no matter how normal I tried to seem, it was never quite going to happen. I needed to re-brand. What style is good for an awkward teen who gets good grades, is afraid to break the rules, and still doesn’t want to stand out too much? Preppy! So I quickly filled my closet with tank tops and sweaters with bows bought on clearance at Abercrombie and Hollister. This was my uniform for a while. Almost all my clothes were in three colors: Navy Blue, Maroon, and Grey.
Over the next few years I slowly built up and expanded my preppy wardrobe with finds from clearance sales, TJ Maxx, and gift card shopping. At one point I owned three pairs of boat shoes and thought a sweater with a collar peeking out from underneath was the ultimate ensemble.
The style fit me at the time. It helped distinguish me, but it wasn’t something that was too open to ridicule. I was studious, opinionated, and a goody two-shoes. I slowly started to change my style once I got to college. Now with those years far behind me, I cringe. Here’s why:
As I said earlier, I just didn’t have the money to pull it off. I didn’t grow up poor. I never had to worry about food or housing. My parents had money for us to do extracurriculars and take us on vacation. The kind of money to comfortably afford Vineyard Vines, Ralph Lauren, and Lilly Pulitzer would have been a level of privilege a bit beyond what I had. There’s definitely styles that are much easier to attain on the kind of budget I was allotted. Also, the preppy aesthetic is associated with old money, the descendents of tycoons, and political dynasties that go back decades. I was badly trying to jam myself into an aesthetic that was not meant for a middle class girl whose ancestors immigrated here too late to be part of those old money families.
Also, I didn’t realize the implications of the aesthetic (if that makes sense). To me, preppy is a very Republican style. I was never Republican. I did not realize this when that was my style. If it isn’t quite Republican, it at least represents a status quo. While I was timid and afraid to rock the boat too much back then, I always had an incredibly strong sense of justice and I was not afraid to share my progressive opinions when I felt like I needed to. It’s hard to truly be a woman of the people when you’re dressed like a narc.
Lastly, I think I’m a little too quirky for a style that’s so rigid. I always have been! I kind of wish I wasn’t so afraid to show it. I can’t necessarily blame my teenage self for being so afraid of being different. I think the need to conform (at least mostly) is normal for that age. I’m so much more happy now that I’ve embraced my weirdness. I wish I could go back and encourage my younger self to do the same.
All in all, I suppose there are worse phases I could have gone through as a teenager. I’m glad I can now laugh at a former version of myself. I think that means I’ve actually grown quite a bit.
