Hit the road, Jacks.

Skateboarders were, for a long time, something like modern-day outlaws, getting into shenanigans wherever there was a rail to ride or a little old lady to scare.

A recent post on A Time To Get got me thinking about how "totally rad" this subculture is and how much more I want to learn about the sport and the people who have made it so gnarly (especially the girls because there are so few of us but especially the boys because they are so darn cute).

Skateboarding, surfing, and that whole California thing have, in the past fifty years or so, come to define the American youth. Think of Lords of Dogtown, the X Games, the Beach Boys. Tony Hawk on a box of Frosted Flakes.

The whole wide world has gone to the boards.

And for the past six months I have cruised all over New York City on my American-made Zig Zagger, put together by the pros at Autumn.

My deck (and my carefully honed ruffian persona) would be nothing without this dirty pair of Jack Purcells which have seen me through many long nights and epic rides. I may not be the fiercest hooligan on the street, but I know a good shred when I see one.

The Jacks look jaunty with shorts and fresh to death under a sun dress. Together these summer staples (skateboard and sneaks) have cruised seamlessly into fall, and keep my street cred alive and kicking. Or so I tell myself.

All pieces, from the selvedge shirt to the chambray frock, are by J. Crew.