We found Kirt Brown doing time at the Brickyard Shopping Center, shuffling down the long corridors, shackled to his mom. His uniform–supersized, soft, and slouchy–mumbled something about classroom comfort.

But our Fashion Wardens aren’t easily fooled. They isolated the look in solitary until it spilled the whole sorry tale.

The primary suspect: long shorts. Their artificially used and abused patina evokes a world-weariness our fresh-faced fashion plate can’t possibly have achieved in his tender 14 years. Beverly Gordon, in her essay “American Denim,” claims such prefab wearywear reflects a longing for counterculture credentials no longer on the market. Even the lingo–“stoned,” “washed out,” “distressed”–has been displaced from life to jeans, which now weather trying times among rocks and bleach, while pampered youth simply hip hop to the Gap to buy into the “been there” look.

The cut is big: sagging waist, drooping butt, cuffs scraping below the knees. According to Clarence Lusane, author of Pipe Dream Blues: Racism and the War on Drugs, low-slung slacks (along with knotted bandanna cap, absent here) are imported straight from prison, where the ban on belts drops trou and sweat-soaked kerchiefs can double, in a pinch, for gang insignia. As teens shuttle between ‘hood and hole, high-security style is paroled from big house to home to Home Shopping Network.

The shirt confirms the suspicion, with its classic inmate stripes and block-lettered “GIRBAUD” stenciled across the back ID-number style.

Brown accessorizes the look with a self-inflicted buzz cut, lock-down short, and spotless Air Jordans over matching Nike anklets. His high tops are groomed with the same obsessive attention that leads inmates of the Cook County Juvenile Temporary Detention Center to plead for the privilege of a spare toothbrush. In the confines of their cinderblock cells, underage offenders brush prison life from their soles, as though pristine sneakers, or their airborne namesake, might inspire a sprint to freedom. The streetwise Fashion Statement? “Already did it.”

Art accompanying story in printed newspaper (not available in this archive): photos/Yael Routtenberg.