How to Dress Comfortably (Yet Practically) for Summer Road Trips

what to wear on a road trip - man with dufflebag getting into c3 corvette

Time to get out of town.

The great American road trip has been a summer tradition for as long has there have been roads… and cars to drive over them. Fumbling with unfamiliar radio stations, maps, and coins for the toll booth have given way to modern conveniences like aux cords, Waze, and E-ZPass and FasTrak, but even all the ergonomic advances in car seat technology haven’t made it much easier to spend six hours crouched behind the wheel.

This summer, invest in your own comfort by following our guide to feeling your best—and still looking stylish—when you hit the road.

The Shirt

→ Recommendation: Short Sleeve Henley

Your nice polos and resort shirts will have plenty of time to shine once you reach your destination, but I’ve come to rely on the short-sleeved cotton henley as my favorite shirt for some serious driving.

Blending the comfort of a T-shirt with the dressier philosophy of a polo with a touch of insouciant ruggedness, a henley with its short placket semi-buttoned seems to embody the free spirit of the road. You can look for one with a pocket to store your sunglasses or just clip them over the unbuttoned placket for easy access.

As far as colors, you can’t go wrong with the Primer-approved thin white cotton henley that’s also been favored by on-screen road trippers like Ryan Gosling in Drive and Daniel Craig’s James Bond. Of course, if your road trip agenda includes scarfing down fast food burgers, you may prefer a color that would better hide Big Mac sauce stains.

The Jacket

→ Recommendation: Rainproof Shacket

On a sunny day with temperatures climbing, the last thing on your mind might be pulling on another layer, but a wise mantra on the road (and in life) is to expect the unexpected, whether that means changing a tire in the rain or the more pleasant surprise of grabbing a bite at a restaurant overcompensating for 90-degree weather by blasting the A/C.

You may never need to wear it, but you’d be smart to keep handy a lightweight jacket, preferably in a material treated to withstand some rain. Any jacket style would work, from bombers to truckers, but I like the versatility of a shacket that can also double as an unobtrusive top layer as needed.

Chances are that if you have it ready, you’ll never even need it!

“I travel not to go anywhere but to go. I travel for travel’s sake. The great affair is to move.”
– Robert Louis Stevenson, Travels with a Donkey in the Cevennes

The Pants

→ Recommendation: Army Green Cargo Pants

buck mason cargo pants

Buck Mason

It may be tempting to reach for sweatpants or shorts, especially if you’re a driver who values comfort most, but – even at rest stops – I think there’s some value in a more intentional manner of dressing than sweats. You could make an argument for shorts but, especially if you’re blasting the A/C against heat outside that’s 90 degrees and rising, the skin on your shins may thank you for covering them up.

Some may be bemoaning the return of cargo pants, but they’re a sartorial gift to road trip drivers as the side-rigged pockets offer an alternative to the orthopedic nightmare of a wallet lumped in your back pocket for hours on end as well as a more accessible alternative to being crunched over your thigh in a front pocket.

Luckily, modern manufacturers seem to have recognized that cargo pant form can still meet function, offering sleeker fits that more flatter profiles so you won’t look like you merely updated your 8th grade closet when you get to where you’re going.

(If you still need to be convinced, read about their military heritage as an element of British battle dress!)


canvas sneakers from vanishing point

Canvas sneakers from Vanishing Point

The Shoes

Recommendation: Low-top Sneakers

Shoes are a bulky thing to pack, especially for the summer when the rest of your clothes are going to be lighter, so you’ll want to save space by wearing shoes that you’ll also want to have when you reach your destination.

That said, your feet will need to be nimbly able to navigate between the brake and gas pedals (and clutch, if you’re so inclined), so you’d want to avoid the flapping clumsiness of your beach sandals. Boat shoes and espadrilles could work better in a pinch, but you’d probably be best-served by a pair of low-top, lightweight sneakers with cushioned insoles.

Of course, the color would be dealer’s choice—or driver’s choice, in this case—though I prefer all-white low-tops as a nod to my favorite movie driver, Kowalski in the original Vanishing Point.

“A journey is a person in itself; no two are alike. And all plans, safeguards, policing, and coercion are fruitless. We find after years of struggle that we do not take a trip; a trip takes us.”
– John Steinbeck, Travels with Charley: In Search of America

The Watch

Recommendation: Chronograph

You’ve got a car clock and a phone, do you really need another way to know the time?

Maybe you picked up your dad’s habit of regulating rest stops or maybe you just want to make a grand show of checking the time when asked “are we there yet?” for the millionth time.

Either way, there’s always a reason to wear a wristwatch. Even if you’ve joined the masses who have adopted smartwatches, use the road trip as an opportunity to disconnect from the distractions of texts and other notifications by strapping back on a analog wristwatch.

In the spirit of the road, a racing style chronograph with its trio of sub-registers suggests that you belong behind the wheel. Check out Primer’s favorite chronographs—and how to use them.

Timex Chronograph

Timex Chronograph, One of Primer's Best Watches Under $200

Tortoiseshell sunglasses

The Sunglasses

→ Recommendation: Tortoise Acetate Sunglasses

You got an early start to the day, the right music is playing, and you’re coasting up the freeway as the sun starts coming up into your sightline. With the right pair of sunglasses, you’re now king of the road.

In my experience, the perfect road trip sunglasses have lightweight frames, polarized lenses to protect your eyes, and—perhaps for more aesthetic purposes—classic-inspired style. Last summer, we heralded these tortoiseshell Carfia round-framed sunglasses made from a light, flexible acetate that resists breaking or bending after being tossed into your bag or pocket. (Though we imagine Primer readers treat your specs a little better than that!)

The Persol-inspired design touch—without the Persol price tag—adds a dash of Steve McQueen style to your road fit… but that’s no excuse to start racing any black Chargers you encounter on your journey.

David King Duffel Bag

The Travel Bag

→ Recommendation: Leather Weekender

Whether you’re traveling solo or have someone riding cockpit, you’ll find it considerably easier to have a bag with outside pockets that can be easily navigated without having to rifle through everything you’ve packed just to find that spare phone charger.

The handsome David King & Co. extra large duffel in tan leather is still one of our best weekenders for less than $150, with room for everything you’d need for a weekend (or more) and plenty of pockets along the outside to slip in your road-ready items.

C3 Corvette

Read more about Andrew's experience buying his Corvette.

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Nick Guzan

Nick Guzan is a public relations consultant and writer living in Pittsburgh. He blogs about men's style in movies and TV at His interests include old movies, muscle cars, maritime disasters, fast food, and single malt Scotch.