8 Travel Shoes to Make Your Holiday Trips Slightly Less Terrible

'Tis the season to invest in some slip-ons

November 9, 2023 12:53 pm
a collage of the best travel shoes for men on a runway background
With holiday travel on the horizon, you'll need a trusty pair of airport shoes. These are the best.
InsideHook/Getty Images

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In the year of our lord 2023, we’re beyond lamenting the woes of holiday travel. (We have already done this, to be fair.) It will be heinous. It will be awful. Much of it will be spent on our feet, in traffic or rolling an overstuffed carry-on through days-old slush. So instead of whining, we’re doing the sensible, adult thing, and planning for this intrusion. Item number one to take care of? That’d be commandeering a pair of the best travel shoes we can find.

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The Best Travel Shoes for Men

This is a trickier task than it might first appear. After all, there are plenty of types of travel and tons of shoes that generally suck at delivering a painless experience whether on the road or in the skies, and after you’ve arrived at your destination. That is where we come in — as jetsetters, pro travelers and glorified test monkeys, we’ve put dozens of styles to the test when traversing TSA, I-95 and everything in between.

What Should You Look for When Buying Travel Shoes?

As we previously mentioned, there are tons of types of travel, but some universal rules of thumb stick out when choosing the best travel shoe for your upcoming journeys. Comfort should trump aesthetics every time (warning: ultra-push trainers can cramp the foot on six-hour flights) and shoes that prioritize breathability and easy adjustment or removal naturally make a ton of sense.

Perhaps these instructions strike you as vague, or perhaps you just don’t want to hunt through the thousands of boots and sneakers clogging up the interwebs or your local DSW. We got you covered, with eight expertly-selected picks that we’ve personally used to traverse the continent, and in some cases the globe. There are ultra-popular Birkenstock slides, versatile Cheslea boots, artesian clogs and much, much more. Choose what feels right for you, and remember that your gate agent is a person, too. Below, the best travel shoes for men this holiday season.

The Travel Shoe to Rule ‘Em All: Birkenstock Boston Shearling-Lined Clog

As we mentioned, we’ve flown, driven and Ubered in dozens of shoes, and, to exactly nobody’s surprise, our go-to travel shoe remains Birkenstock’s wildly popular Boston clog. Snug enough to surefoot your way through baggage claim or up an icy driveway, all while remaining incredibly easy to slip off on the JetBlue flight (just put them back on before you go to the bathroom, please), they’re sensible, pack down beautifully, and, if you secure a pair of the shearling-lined versions, beefy enough to deal with chilly temps. Do yourself a favor and just buy a pair already.

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The Snuggly Slip-On: The North Face ThermoBall Traction Mules V

If Birkenstock’s behemoth isn’t quite your speed, The North Face offers a sleeping bag-style alternative in their ThermoBall Mules, a weatherproof slip-on that’s designed with the same technology as the outdoor brand’s best-selling jackets. A collapsable heal makes them just as easy to pull on, and their crunchy, semi-bulbous look should do enough to appease crunchy and hypey travelers alike.

The Dressy Option: Yuketen Bit Loafer

Traveling for work? Jetsetting for a wedding? Luckily for you, Yuketen’s Bit Loafer offers a smart option that is still a joy to earn skymiles in. Crafted from an Italian-tanner leather that’s hand-sewn by leather artisans in Maine, these loafers are set atop an original rubber camp sole, providing a flexible and forgiving alternative to the typically stiff dress shoes outsole. Trust us, they’re worth every penny.

The Do-It-All Travel Boot: Blundstone 510 Classic Boot

Of course, not everyone has the luxury of galavanting around in slippers. Whether your trip necessitates packing light or some serious TOT (time on toes), Blundstone’s versatile Chelsea is the only way to go. Built on a sturdy outsole and featuring signature pull tabs for easy on-off-ability, they can handle literally anything you throw at them — an eight-hour drive, a serious snow shoveling session or just the approving looks for local buddies and former high school crushes.

The True Travel Slipper: Ugg Classic Mini Boot

Grow up. Uggs are for everyone, and anyone who says otherwise is denying themselves the pleasure of a snuggly-wuggly experience for the dogs. Just make sure you were socks, else risk hateful eyes in the TSA line.

For Serious Sneakerheads: Nike ACG Mountain Fly 2 Low Sneaker

Laces? In the airport terminal? Even the most dedicated sneakerhead — the one to rock, ten to stock among you — will agree that it’s a hard no. So what to do? How will people know that you are insufferable, and you will happily talk to them about it? Salomon is the easy answer, but we’d suggest a deeper cut from Nike’s latest ACG drop. The Mountain Fly 2 Low has a similar lace toggle for easy adjustments, but we find it’s cushy foam midsole —designed for tackling tough terrain — to be kinder on the underfoot than the average technical shoe’s rock-hard sole plate. Plus, they go very hard.

The Celeb-Endorsed Kicks: Lusso Cloud Scenario Slip-On

Celebs, they’re just like us! In the sense that they also love an affordable slip-on that still counts as a socially acceptable shoe, despite being breathable af thanks to a preferred foam design. Shawn Mendes, Justin Bieber, a Joe-Bro and more have all been spotted rocking Lusso Cloud’s airy slip-ons around town, and that’s just the tip of the iceberg.

The Trendy Travel Flex: Gardenheir French Recycled Hemp Garden Clogs

Travel shoes are all about comfort, functionality and ease…but that doesn’t mean you can’t get a ‘fit off while you’re at it. This hemp clog from Gardenheir, chic garden supply importer for and menswear brand extraordinaire, is weatherproof and makes total sense for cross-country flights, but also ticks all the swag-goo boxes we’re looking for in 2023 — tastefully minimalist, built to be worn with chunky socks and generally indicative that you have a standing date with McNally Jackson for your monthly mag pickup.


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