Haute couture: not quite dressed

The other day I saw a teenage boy sort of tiptoe-shuffling his way down the sidewalk in what I'm sure, if you move in the right circles, was a very chic outfit. He wore a jacket, a bulky sweatshirt, plaid boxers, jeans belted entirely below his ass, and unlaced sneakers into which he had inserted his feet only half way. Is this a new trend? For those who want not only their butts, but also their heels to garner the benefit of a refreshing breeze? Niiiice.