Road Warriors

When you're hauling ass down Route 66 in a T-top Trans Am, your gear should match the landscape

Actually, it doesn't matter what highway you get your kicks on. Route 66—the storied stretch of asphalt running from Los Angeles to Chicago—may have been immortalized by Nat King Cole and the Stones, but whatever stretch of road gets you and a buddy the hell out of Dodge this summer will do. Question is, what do you pack when you're channeling Wyatt and Billy from Easy Rider?

Not thought-out outfits, that's for sure. All you really need is a duffel bag in the backseat with a motley assortment of pieces spilling out, any of which can be pulled on or off anytime. That means: layers that can be shucked as the weather (and finicky A/C) demands, denim shirts that look better wrinkled, and the kind of sun-bleached chinos that wear coffee splashes and French-fry grease like badges of pride. You want it all distressed, dusty, and worn-in—just like the highway itself.—Will Welch

On Arthur: Tank top, $70 by T by Alexander Wang. Shorts, $68 by A|X Armani Exchange. Jacket (beneath him) by Neil Barrett. Boots, $100 by Clarks Originals.

**On Stephanie: **Camisole by Michael Stars. Panties by Betsey Johnson Intimates. Bracelet by Scout.