Somewhere along the line I got fairly preppy in my fashion style. I went from dressing like a little boy, to not really caring, to grunge, to punk, to looking like I was plucked from Union Pool in Brooklyn on any given night, to where I am now: preppy. I think at first it was almost me being ironic the way I matched up my personal appearance with a look that didn’t seem to complement each other very well, but still somehow worked. It’s funny to be sitting at a restaurant in a very conservative dress, pearl earrings from Tiffany and an almost completed half sleeve of tattoos. It’s almost as if I’m having an identity crisis, when I’m actually not. I think maybe I’ve always been on the preppy side but just didn’t embrace it until now.

As I prepare to leave New York City yet again for another month (off to Colorado to visit my sister), I’m weeding out what I’ll be taking and what will be boxed up and left behind so as to make room for girl subletting my place while I’m gone. While doing this, I’m realizing that, jesus fucking christ, I’m not packing for a month in the mountains of Colorado, I’m packing like I’m headed out to the Kennedy Compound in Hyannis Port! It’s like J.Crew threw up in here and there’s nothing I can do about it but be forced to wear it all!

Here are some key items that your wardrobe must have if, like me, you’re delusional enough to think your invite out to Hyannis Port is just an email away.