What We’re Wearing

Road Trip

What We’re Wearing

Road Trip

Easy, breathable layers for long drives and spontaneous stops

Men's road trip outfit

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.

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Your On the Road Fit

Men's road trip outfit inspiration
alex mill linen chore coat

Linen chore coat,
$250 by Alex Mill

buck mason field-spec t-shirt

Field-spec T-shirt,
$62 by Buck Mason

roark pro traveler pant

Pro Traveler pant,
$99 by Roark

jcrew suede camp shoe

Suede camp shoe,
$198 / $138.99 by J.Crew

noah striped sock

Striped sock,
$24 by Noah

levi's heritage tote

Heritage tote,
$64.50 / $45.15 by Levi's

walden airman sunglasses

Airman sunglasses,
$99 / $49 by Walden

carhartt harlem cap

Harlem cap,
$48 / $39.99 by Carhartt

hamilton khaki field watch

Khaki field watch,
$795 by Hamilton

Your On the Road Fit

Men's road trip outfit inspiration

Harlem cap,
$48 / $39.99
by Carhartt

 
 

Airman
sunglasses,
$99 / $49
by Walden

 

Linen chore coat,
$250 by Alex Mill

Pro Traveler pant,
$99 by Roark

 
 

Striped sock,
$24 by Noah

 

Suede camp shoe,
$198 / $138.99 by J.Crew

 

Heritage tote,
$64.50 / $45.15 by Levi's

 

Field-spec
T-shirt,
$62 by Buck Mason

 

Khaki
field watch,
$795 by Hamilton

Take More
Short Trips

Map pin illustration
Map pin illustration

Sometimes an extended weekend away is all you need to hit the reset button. Low-key and low stakes, you can plan them on short notice, unlike a vacation that takes months to save for and is more expensive. Whether it’s 30 minutes away or three hours to the next city, unplug, rest and relax.

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