The 10 Most Comfortable Men's Travel Shoes for 2021

See recent posts by Tyler Schoeber

I’ll admit, in the past I was never the kind of guy to care much about footwear: I’d just slap on a pair of Payless favorites and call it a day. As I’ve gotten older, though, I’ve found that a decent pair of shoes can go a longer way than I thought. Think about it—we’re constantly on our feet, so why not feel good and look good while you’re at it? Without further ado, these are the most comfortable men’s travel shoes.

Cole Haan GrandPro Rally Sneaker

I’m a true Cole Haan fan. A Cole Faan, if you will. The GrandPro Rally Sneaker in this soft matte brown color is stylish enough to rock with any look yet light enough to keep your feet cozy for miles. Whether you’re traveling, commuting, or kickin’ it back, these sneaks are a seriously cool option for any occasion.

Converse Chuck Taylor All Star ’70 Hi

A classic pair of overworn, dirty Converse has been a summer staple of mine for as long as I can remember. Probably my favorite thing about these is that the style hasn’t changed at all since my dad was a kid, which is pretty impressive. By maintaining that timeless look for years on end, these will match your style whether you’re 6 or 60.

Allbirds Wool Runners

I had to talk about Allbirds’ Wool Runners because they’re such a SmarterTravel favorite—and I’m not sorry. As some of the softest sneaks I’ve ever slipped on my feet, these babies are simply foot clouds. Because they’re designed to be temperature-regulating and moisture-wicking, seasonality doesn’t matter much for these; they’re stellar no matter the time of year.

Everlane Court Sneaker

I’ve long been a fan of Everlane because of its sustainably made, affordable line of stylish products, so I knew I was going to love these Court Sneakers before I even saw them. I really dig the subtle pop of mustard yellow here, fitting the vibe when I’ll wear them on sunny days in the city.

Brooks Addiction 2 Walking Shoe

Any guy on his feet all day knows that the Addiction 2 Walking Shoes are built to withstand constant day-to-day use. The slip-resistant design and serious cushion support keep these shoes as comfortable as the day you bought them even if you put them through hell.

Vans Classic Slip-On Core Classics

No laces? Sign me up! These slip-ons have been right under my nose for years and I never gave them a shot, but I’m glad I did—they’re the easiest shoes I’ve ever worn. With just a quick, last-minute slide-in, these shoes will have you out the door and ready to start your day in seconds.

Birkenstock Arizona Sandals

When it comes to walking sandals, it can get a bit tricky picking a pair that can handle a full day on-the-go. That being said, I was initially drawn to Birkenstock solely due to its Arizona design, but was incredibly pleased with how my feet felt after days of wear. I sported these for four days straight at a music festival and wouldn’t have changed a thing.

Bruno Marc Men’s Rivera Oxford Shoes

If you’re looking for a more affordable option to rock this season, check out these oxford sneakers from Bruno Marc on Amazon. Sold for under $40 and offered in more than a dozen colors and styles, these are a worthy sneaker to get you here or there.

UGG Neumel Chukka Boot

If you thought that UGG was generally a women’s brand, think again. These handsome chukkas are an awesome alternative to your regular day boots, offering a breathable yet wildly soft, fuzzy interior for maximum foot-huggage. If you think you need to store these away in the back of the closet when the weather warms up, think again—these babies can work as your go-to indoor slipper until they’re ready to go outside again next fall.

York Athletics Henry Sweatshirt Sneakers

These are meant for the kind of guy who commutes to work in a suit but doesn’t want to commit to dress shoes on the subway. Revamping the look and feel of your all-time favorite gym trainer with modern leather accents, these sneaks are ideal for work, play, and everything in between.

Tyler Schoeber is a production specialist, photographer, occasional writer, travel style guru, and general Renaissance man. Follow his adventures on Instagram at @tylerschoeber.

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