I’d start by saying I wrote the book on preppy, but I most definitely didn’t. I know this because it was The Preppy Handbook that first blew my mind in the summer after 5th grade. I remember, specifically, being in my sisters room and asking her what it was.

her: It’s a handbook about preppy style
me: What’s preppy style?
her: It’s a style.
me: What’s a style?
her: It’s just, like.. a way to dress.
me: What do you mean? (I asked an insane amount of questions as a kid.)
her: (getting annoyed) It, I dunno.. it’s just like a way.

Round and round until I got kicked out of her room. That was all it took though. It was the first thing I ever remember not understanding at all, so I had to find out. I read the whole thing, twice. I wore all the clothes and I constantly was asking my sister for approval. Are these preppy? What about these? O.k.. and these? I’m sure at some point she wished I had never seen it sitting on the bench in her room, or wasn’t so weird to actually be drawn in to that madras cover or he/she diagrams of weekend sporting outfits, but I was. I can tell you what I wore that summer.. all summer. Sperry top-siders, IZOD sporty shorts and a Lacoste/IZOD shirt. Total goon.

There are only a few things I’d claim to starting in my home town, at least in my and surrounding grades, and hear they are: Madras and/or fruity colored shirts, black loafers.. (all mine except for the loud senior in my Latin class.. ) and tapering your pants (learned from California Lomas). Except always from the knee, which was one of the finer details that was just plain ignored, so everyone would only do the cuffs and end up with a funny haz-mat suit look. No, this isn’t bragging.. more like shamefully admitting. Though I will brag that if you gave me an L.L. Bean catalog right now, I could “yes, no, yes, yes, no, only if you’re really hunting for quail, yes, no” the whole thing faster than you can turn the pages. Like riding a bike, some things you never forget.

My point of all this is, any preppy chump knows that top-siders are like preppy 101. The shoe you wear until you realize that every preppy dad and wine chugging Martha’s Vineyard mom wear them with their whale pants hiked way too high. What I’m saying is, they just aren’t that cool. Not then, and not now. Any prep school freshmen can tell you that a four hole blucher moccasin is cooler in every way, shape or form. If the hipsters must get on it.. this is what they should be getting on. All I can think of when I see their colored top-siders underneath those silly no-butt girl pants is “what a bunch of n00bs”. Combine that with those trashy Filenes Basement big-knit and too-long cardigans? Oof, you’re killing me. Stick to the neon sunglasses and leave the east coast footwear to the professionals, dudes.