Photograph by Philip Sison
Style Necessary Style

An illustrated guide to preppy style: at work, at play, at sea

New and classic staples that look the part.
Giancarla Espinosa Aritao | Nov 06 2018


Functional pieces, such as a classic polo shirt and a hat, score points whether you are on or off the greens. If you keep the colors unexpected, the look stays faithful to the personality of preppy, known for spawning multicolored plaid pants.


Ditch the tie for something more laidback. But prep casual is always thrown together with precision. That means never crossing the line of looking too casual. Pick easy items like a button down shirt and khakis, but keep it tailored by adding textures through layering.


The concept of preppy as power dressing came to its apex in the ‘80s, when economies were booming and greed was good. Channel Wall Street by donning a classic suit—never cut too slim or tight—and reinvent Gordon Gekko by adding a throwback piece like a waistcoat.


Test drive trends at night. Live a little with patterned bowties and shirts, but keep the rest of your clothes simple. Pattern-mixing should be approached the same way you would good wine. Savor each note, but do not have too much.


Few situations embody the lifestyle of an unabashed preppy than sand and sea. It is sealed by images of a young JFK on a yacht and the ads of Tommy Hilfiger. Invoke its carefree spirit by donning the triumvirate of beachwear: bermudas, boat shoes, and a luxurious sweater.


Photographs by Philip Sison

This story first appeared in Vault Magazine Vol 5 2012.