What We’re Wearing

Road Trip

You can see the end of summer on the horizon, but it's not over yet. In fact, between “summer Fridays” or well-timed vacation days, not to mention an upcoming long holiday weekend, you've got a few chances left for a leisurely weekend getaway. Why not hit the road? There's something about a good road trip that feels both spontaneous and deliberate. Maybe it's the promise of an open highway, a perfectly curated playlist, or the fact that time bends a bit differently when you're behind the wheel with nowhere to be for a while. But whether you're heading out for a weekend getaway or just cruising a few hours to visit friends, what you wear matters more than you think—comfort is key, but you still want to look like the guy who's got it together when you roll up to the gas station or check into the motel.

The ideal road trip outfit strikes a balance between easy movement and everyday style. It should be soft, breathable, and layer-friendly—something that won't wrinkle or overheat, even after hours in the driver's seat. And because you're bound to make some unscheduled stops along the way (coffee, tacos, roadside attractions), it doesn't hurt to be dressed in something that looks just as good outside the car as it feels inside it. Here's what to wear when you've got miles to cover and a loose plan to follow.