According to the Official Preppy Handbook, one of the most important aspects of prep school is dropping out. Quitting school, intentionally or not, lends a man (or woman) an air of danger, of spontaneity, that most people wouldn't associate with preparatory schools. Rogues Gallery is the brand equivalent of the mysterious kid who dropped out midsemester and disappeared, off to bigger, better, and less academic pursuits. Alex Carleton's line originally put nontraditional art on tshirts that felt ideally worn-in right off the shelf. The graphics were dark but playful takes on the iconography of his native New England. As it grew, the brand moved on to take the relaxed clothing of the region and scuff it up a bit. Sometimes a lot. After all, your favorite shirt is more likely to be the one you wore all through school (where the cuffs got frayed), to the beach (where it got a little sandy), to a dozen parties (where it got soaked in beer), the one that has character, than the one you just took the pins off of.

Eventually the dude who dropped out resurfaced in town. He even got a respectable job. Likewise, Rogues Gallery has grown up a little. Even though they still make artfully disheveled clothing for the weekend, they also craft rad tailored pieces. Their woolly sportcoats are made in the United States by an old-school traditional suit maker. The new knits qualify as refined American sportswear. All of it still has a kernel of storm-weathered maritime spirit, but it's been cleaned up. Like the prodigal dropout. After work, at the bar, he rolls up the sleeves of his crisp white dress shirt, and everyone notices the mysterious mermaid tattoo on his forearm.

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