Dressing for Summer Travel: Road Trips and Airplanes

Sidney Poitier in Lilies of the Field (1963)

Sidney Poitier’s tropical shirt in Lilies of the Field (1963) takes his style to the next level behind the wheel of his road-ready station wagon.

With this summer looking like more of a realistic travel season than last year for those looking to safely get away, I wanted to round up some of what I’ve learned in nearly a decade of paying attention to and writing about style and apply it realistically to how I dress for summer travel!

These guidelines may not work for everyone’s sense of taste, style, or comfort—and I’d always advocate for individuality over blindly adhering to what some non-expert on the internet (yours truly) has to say—but I thought it could be helpful to develop a guide based on what has worked for me, particularly in the wake of takes reporting that some are having trouble rediscovering the purpose of their clothing after spending much of the pandemic locked down in leisure-wear.

Of course, leisure-wear might be all you need to pack for summer vacations this year, but it still helps to have something a little practical for the journey, whether by air or on the road…


In the Air

Much is informed by TSA restrictions, your personal anxiety over losing luggage, and the nature of your trip—dressing for a one-day business trip differs from the free-wheeling bachelor weekend or family vacation—but, for the purpose of argument, I’m writing from the perspective of someone dressing for the typical multi-day getaway.

Die Hard

John McClane may be a less confident air traveler than Mr. “Fists-with-your-toes”, but Bruce Willis’ attire in the air looks ultimately more comfortable than his traveling companion. If only he had kept his shoes on after reaching his destination!
Read more about McClane’s famously deconstructed style in Die Hard in this 2012 post.

Jacket: Ideally, this would be light enough to store easily aboard the plane with plenty of secured pockets that can hold all of your personal items when sending your jacket through the TSA security checkpoint (without having to individually collect them all from a tray). Spending much of your time in an airport or plane means worrying less about a weather-resilient top layer, but I think it’s wise to wear something water-resilient enough to avoid needing to bring an additional jacket for incidental rain you may encounter at your destination.

Liam Neeson in Non-Stop (2014)

As an air marshal in the 2014 thriller Non-Stop, Liam Neeson’s character incorporates his frequent flying experience into a practical, layered outfit that would suit him well even on a flight that didn’t have some degree of mid-air combat.

For this stylish and light yet weather-flexible outerwear, I recommend either a classic Harrington jacket with button-flapped pockets or a waxed coat similar to the Barbour Beacon Sports Jacket that Daniel Craig famously wore in Skyfall, as it has plenty of pockets and the treated waxed cotton shell will keep you dry while still looking stylish either at the airport bar or your favorite vacation hot spot.

Shirt: Comfort and general presentability are my keys. I like a collared shirt that guarantees I’ll still have the ability to be relatively “dressy” as needed, should my luggage get lost or flight delayed before a dinner reservation. Air safety experts advocate for wearing long pants and long sleeves on a flight (and avoiding more flammable synthetic fabrics), adding a layer that protects the skin should you find yourself needing to escape in an emergency situation. Given all this, I recommend a long-sleeved cotton polo shirt or button-up.

Trousers: As with the shirt, I opt for comfort and presentability as well as flexibility, as they’ll need to be comfortable for sitting (and maybe even sleeping!) for hours but then may be pressed into service for dinner or whatever plans await you at your destination. A darker color can hide any potential sweat-stains, spilled drinks, or other calamities of travel, so I like dark gray chinos, again constructed primarily from cotton.

Belt: Depending on your airport regulations or the level of TSA screening you’re subjected to, it’s a safe bet to assume that belt-wearers will need to remove them before moving through security. This in itself could make a good argument for wearing beltless trousers, such as those tailored with side-adjusters or fitted with the hybrid belt loop/side-adjuster style offered by some manufacturers.

Keeping this in mind, you’re probably still fine to wear a belt that you planned on wearing for you trip and just make sure your trousers fit well enough that you won’t be exposing any more of yourself than you should when removing said belt in the security line!

Shoes: Be kind to yourself—and those behind you in the TSA line—and opt for footwear that can be easily taken off or put back on when passing through security while still stylish enough to serve you well at your destination. I like Chelsea boots for travel, as their ankle height is compatible with the prescribed long trousers, and their elastic side gussets and lack of laces ensure an easy on/off experience whether going through security or daring to relax in your socks (which you shouldn’t take off!) on the plane. Depending on the nature of your trip, Chelsea boots should be appropriate for the more formal situations you encounter, mitigating the need to pack any more formal shoes. Whatever shoes you wear, remember to walk around barefoot on a rug once you get to your destination, making fists with your toes… “better than a shower and hot cup of coffee.”

My personal preference are my “antique brown” leather Blundstone Super 500 boots, still available from Amazon and Blundstone as of May 2021.

Steve McQueen in The Thomas Crown Affair (1968)

Even for a less conventional method of air travel, piloting a glider through the skies over Massachusetts in The Thomas Crown Affair, Steve McQueen dresses practically in his navy Harrington jacket, Persol sunglasses, side-adjuster chinos, and suede boots.
Read more about this outfit—based on the King of Cool’s real-life sartorial sensibilities—here.

Watch: While there’s little trouble adjusting any mechanical watch to the time zone of your destination, choosing which watch to wear for air travel could be a fun opportunity to celebrate the theme of your adventure with a classic pilot’s watch (think the Rolex GMT Master… or a more budget-friendly alternative) as well as making sure the bracelet of said watch can be easily unbuckled can slipped into that jacket pocket—or luggage pocket—to pass through security without worrying that your watch will be damaged.

A steel pilot’s watch on a metal bracelet would be stylish and sporty but still dressy enough for universal wear during your trip.

“Assuming one has a convenient pocket…”

Many a style writer seem to underestimate the value of pockets, and situations like air travel particularly shine a light on the importance of having accessible and ample pocket space (without walking around dressed like John Milius.) I would make sure your jacket, trousers, and shirt allow you to keep handy:

  • Phone
  • Wallet (for presenting your ID… and presenting your credit card for in-flight drinks!)
  • Printed travel items
  • Chewing gum (for countering ear pops and freshening breath after an in-flight nap)
  • Earbuds or AirPods (to avoid having to dig around your carry-on once you’re aboard)

I don’t think your air travel attire needs to accommodate space for glasses or keys, which can be packed away in your carry-on luggage. I also like to keep a device charger either in my jacket or carry-on.

Read more about skyway style in the BAMF Style archives.


On the Road

It’s easier to have a little more fun with this one and, assuming the rest of your luggage is in more accessible reach than for air travel, you don’t need to be dressed quite as much for contingencies. That said, I still take a more strategic approach to dressing for a few hours on the road.

Jon Hamm as Don Draper on Mad Men (Episode 7.13: "The Milk and Honey Route")

Don Draper (Jon Hamm) frees himself of his corporate lifestyle in Mad Men‘s final season, dressing for an extended drive through middle America in a blue Derby-style jacket, plaid sports shirt, undershirt, slacks, and his signature American Optical aviator sunglasses as seen in the penultimate episode, “The Milk and Honey Route”. Read more about Don’s road layers as he drifts back toward his blue-collar Dick Whitman identity in this 2018 post.

Jacket: Depending on how you manage your car’s internal temperature, you may not be wearing a jacket for most—if any—of your time behind the wheel, but I like having an outer layer handy should you encounter inclement weather… or a passenger who takes a little too much ownership over the A/C knob.

For me, the ideal road trip jacket is a nylon bomber jacket, typically a lighter-weight alternative to the fully insulated Alpha Industries MA-1 (though those are recommended for any man’s closet!)

Shirt: Layers are my go-to for road trips, specifically a short-sleeved button-up over a T-shirt. Sure, going sans undershirt avoids the unfashionable “T-shirt triangle” over the chest, but wearing one provides some climate-informed flexibility while also allowing the overshirt to stay clean if it needs to be removed for unexpected situations like changing a tire or de-layering to catch a few winks.

Shirt pockets are rarely efficient storage, but I find them to be useful in these situations for glasses and toll passes, as needed. These are also items that can be kept somewhere in the car’s console, of course, but storing them in your pockets assures that they won’t fly out of place after taking a hard turn while also avoiding the risk of leaving them in view of any opportunistic passersby with larceny on their minds while you’re at a rest stop.

Steve McQueen in The Hunter (1980)

While not as sleek as his famous style behind the wheel in Bullitt (1968), Steve McQueen’s nylon bomber jacket, dive watch, jeans, and sneakers for his final role in The Hunter (1980) set a template for comfortable and practical road gear.

Trousers: Summer vacations may be the only time some men bring out their shorts, but I still like to avoid these for road trips. For me, there’s a personal presentability factor (though I doubt anyone in the roadside rest stop outside of Terre Haute would judge), but long pants also allow you to blast your car’s A/C without your legs freezing. As with air travel, I like darker colors for trousers, and the rigors of the road are also a welcome opportunity for more rugged cloths like good old, reliable denim.

My go-to pants for road trips are trusty dark blue jeans—my preference are Levi’s 541 “Athletic Fit” in marbled “desperado” wash—which feel like a relatively fashionable and contextually appropriate choice.

Belt: Hunching over a steering wheel for hours on end can be uncomfortable enough on its own that the last thing you need to add to the mix is stiff leather or metal digging at your mid-section. While some of BAMF Style’s more athletic readers may not encounter this issue, your—uh… curvy?—author often finds that regular belts have a way of finding and assaulting fatty parts of my torso during road trips… an issue not helped by said author’s preference for incorporating Arby’s, Taco Bell, and Waffle House stops onto the journey.

To combat this discomfort, I’ve found myself favoring the flexibility of a surcingle belt or web belt when I know I’ll be driving for a distance, often picking ones echoing the colors or themes of the rest of my outfit and accessories for a touch of character. It helps that I also like wearing belts like these when I’m on vacation so they’re not at odds with summery destinations.

Shoes: Keeping comfort in mind, I like wearing shoes that are ready to withstand—and survive—any unexpected roadside calamity, be it a roadside tire change, trekking for gas, or needing to stop in a rainy, muddy area… or just navigating the waters of a poorly maintained gas station bathroom.

Unfortunately, the sleek, comfortable, and appropriately named suede moc-toe drivers are rarely up to these tasks, so I like solidly built sneakers with cushioned insoles, though Chelsea boots or chukka boots would also be a more stylish alternative for those gents who don’t like sneakers.

Barry Newman as Kowalski on Vanishing Point (1971)

The dearth of pockets isn’t quite my style, but Barry Newman’s classic and minimalist outfit for Kowalski’s iconic journey behind the wheel of a 1970 Dodge Challenger R/T in Vanishing Point (1971) blends several wardrobe staples for an ultimately timeless road rig.

Watch: This is a little more of a form-driven choice than function given that your phone, GPS, and car clock are all reliable ways to serve any purpose. Depending on where I’m going, I’ve found my favored road trip watches to be either a steel dive watch on a nylon NATO strap that absorbs sweat and can be changed out with other bands (for beach trips) or a gunmetal field watch on a brown leather strap (for more adventurous getaways.)

“Assuming one has a convenient pocket…”

  • Phone
  • Wallet
  • Cash and currency (for paying tolls, parking, or nabbing quickie rest stop items)
  • Sunglasses or other glasses
  • Car keys (obviously not while driving, but consider where you’ll be pocketing them at rest stops)
  • Pocket knife or multi-tool (as legally permissable)

Read more about dressing for the road in the BAMF Style archives, or take a closer look at some of my favorite examples:


How to dress once you’ve reached your destination is a different story, but if you want to take some 007-approved tips for the beach, check out my updated post looking at what’s in James Bond’s Beach Suitcase, recently updated for summer 2021 with affordable finds from modern outfitters!

Looking for even more recommendations from yours truly? Check out this Spotify playlist I curated of some favorite summer travel tracks, transcending genres and decades for a kinetic, feel-good experience that makes the journey as exciting as the destination.

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