STYLE GUIDE: Hack the System in These Classic Preppy Outfits


By @Melizards

Sometimes the best way to be subversive is to blend in…because in the consumerist society we live in, appearances often hold a weighty portion of people’s judgment of character. Patrick Bateman in American Psycho couldn’t have gotten away with his destructive behavior without his dashing good looks and accompanying clean-cut yuppie style. In The Wolf of Wallstreet, Leonardo DiCaprio’s character played a mercenary that hacks the stock market with the panache of a respectable businessman. As the anarchist punk-turned-Harvard Law School lawyer in the film SLC Punk concludes: “we can do a hell of a lot more damage in the system than outside of it.” In essence: conform to reform.

There’s also something endearing about the contradiction of good-guy style with a rebellious agenda. Imagine the feeling of wearing a polo with a sweater tied around your neck while blasting Slayer at 2am. The mundane life of conformity that society expects meets the ecstatic rush of chaos and disobedience that humans crave to ultimately ignite a sardonic pleasure over the discordance of it all.

Whether or not you attend polo matches in the summer, snag yourself some chinos and button-ups from Karmaloop and you can trick people into thinking you just stepped off a 200-ft yacht. Play the game of first impressions right and the opportunities can be endless.


Who would ever expect a rebel to don teddy bears on their pin-striped dress shirt? Stay undercover with the Denim Bear Button Up Shirt by Ezra Wine, which pairs perfectly with The Skate Life Stretch Chinos in Khaki by Diamond Supply Co. Boat shoes tie together any preppy look done right, like The Spinnaker Boat Shoe in Navy, White, & Red by Sebago. Keep your chin and your pants up high with The Manchester Belt in Black by Commune.


Every wardrobe needs a staple black sweater. The Fitted/Crewneck Knit Sweater by Biography Wear also looks great draped over the shoulders. Add a pop of yellow and nautical with The Anchor Printed Twill Chino Shorts in Yellow by Allston Outfitter…which matches impeccably with the anchor on this Emancipated Soul Genuine Leather Bracelet in Black by Profound Aesthetic. Shade yourself from the haters with the Cooper Black Sunglasses from Collins Bridge.


The Carlton Woven Shirt by Filthy Etiquette looks nice and dapper paired with The Week-end Pants in Jungle Green by RVCA. Complete the timeless look with The Billfish 3-Eye Boat Shoe in Tan & Beige by Sperry Top-Sider and The Classic Warwick Watch in Silver by Daniel Wellington.

Recommended For You

Leave a Reply

Your email address will not be published. Required fields are marked *