Dandy and white suit wearer Tom Wolf is credited with first coining the phrase in an article for for Esquire about the elite preps vacationing at Martha's Vinetard. He writes:
The jackets were mostly navy blazers, and the ties were mostly striped ties or ties with little jacquard emblems on them, but the pants had a go-to-hell air: checks and plaids of the loudest possible sort, madras plaids, yellow-on-orange windowpane checks, crazy-quilt plaids, giant houndstooth checks, or else they were a solid airmail red or taxi yellow or some other implausible go-to-hell color. They finished that off with loafers and white crew socks or no socks at all. The pants were their note of Haitian abandon… at the same time the jackets and ties showed they had not forgotten for a moment where the power came from.
- Subdued accompaniments. The most important part of pulling off the "go-to-hell" look well is to not go over the top, or you'll just look like a clown. This means going for an overall "conservative" look with one shocking element. Here, note that the classic look of the sweater, button-down, shoes, belt, and watch really allow the pants to shine.
- Get the color or pattern right. It's called "go-to-hell" for a reason. Now is not the time to be shy. Go with the boldest and most clashing color or pattern possible. Think yellow, salmon, red, or seafoam for solids and big bold plaids for patterns. If you go embroidered pattern route (tiny sailboats, flamingos, or the like), make sure it's something representative of your personality.
- Boat Shoes. Sperrys are a prepster essential, so if you're planning on pulling off the go-to-hell look anywhere near an ocean, make sure to grab a pair.
- Fun socks. Also envogue nowadays. Just 'cause it's too cold to go sockless doesn't mean you can't have fun "down there". Spice up your Sperrys with some fun patterened or striped socks.