LET’S HEAR IT FOR THE BOYS: The Prepster

The prepster is a rare hybrid of the preppy self-entitled schoolboy style with the grunge cluttered aesthetic of hipsters. Madras and boat shoes and Ray-Bans (oh my!) are the holy trinity of Cape Cod chic, so it only makes sense to bring the look back down with acid washed jeans and heavy-handed styling.

This Fashionisto’s plaid gingham shirt is a popular item every spring. Styled with sloppily rolled cuffs and left purposely wrinkled, this shirt gets an A+ for lack of effort. Nothing says Seattle Sound better than a grunged-out plaid that would make Kurt Cobain proud. Blue leather boat shoes add to the authenticity of the preppy mode and the lazy cuff on the faded grey jeans really makes the prep pop. That’s what makes the difference between boating on your parent’s luxury yacht and your illegally built houseboat with Claire Boucher while listening to Grimes. If that reference was too farfetched for you, you should seriously reconsider you time spent on Spotify. Overall we’re left with a look that gives off a laid back New Englander vibe.

These outfit choices are perfect for those almost-spring days. Those days when you just want to say, “Screw it, I’m drinking an iced coffee today,” and then you regret it after the brain freeze and wind chill set in. Untucked and cuffed on every limb, casualness is no excuse for style rules. Take note of how this Fashionisto cuffs his jeans only once — jeans should only be cuffed once, one inch. Otherwise, say chinos or cords, you can cuff them as many times as you’d like in half inch increments. I don’t make the rules, I just call them, so if you’re reading this with jeans cuffed up above your ankle, now is the time to check yourself before you wreck yourself.  

Sometimes the best mash-ups of fashion aesthetics are clothes of one mode worn in the style of another. Whether that means running the dryer a little extra or tucking in your ironic graffiti T-shirt, I encourage you to give prepster a try. It has all the perks of prep with all the sex appeal of bohemian style.

Hint: Sometimes you need to look like you were laid off to look laid back. That means expensive clothes worn like you're broke. Try this lightweight cotton shirt from J.Crew with these super-fine tortoise Ray-Bans. Wear the whole look with these classic Sperry Topsiders and you’re ready to try out prepster-chic. Iced coffee in hand, give those hipsters a taste of their own irony.

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