As temperatures climb and we enter the season of exposed feet, we’re here to help, with all the best tricks for keeping your feet presentable, as well as comfortable. While this week happens to be the start of Fleet Week, we’re doing our own take as summer begins. Welcome to Feet Week on the Strategist.
Since we’re in prime getting-out-of-town season, the Strategist has been thinking about the best travel gear (see what our editors can’t get on an airplane without, and a roundup of the best rolling luggage). Below, our latest conquest: the best travel shoes — shoes that can withstand both the airplane and cobblestones, for men and women.
“These Kenneth Cole shoes are so comfortable: They feel like walking on a cloud, even after the hours I’ve spent wandering on unforgiving cobblestone streets. Because of those tiny little holes, my feet never get sweaty or smelly, and somehow they are indestructible — I wore them on a treacherous hike down to the beach and got them wet and full of sand, and they were just fine.” —Alexis Swerdloff, Strategist editor
Note: These sneakers are sold out, but here is a very similar, equally-comfortable-seeming sneaker from Sperry.
“These work with a nicer workout and you won’t feel schlubby, which also makes them perfect to complete my airplane travel. They’re so comfy and very easy to slip on and off if need be.” —Marissa Berg, director of visitor experience, Jewish Museum
“These are perfect for traveling because they’re a comfortable sneaker but they also add a little height — cute and comfortable.” —Olivia Brown, policy partnerships manager, Lyft
“Traveling or not, I can almost always be found in white Superga sneakers. I’ve gone through so many pairs and styles over the years, but I’d have to say these are my favorite. They’re classic and comfortable enough to wear pretty much everywhere, especially while traveling.” —Steph Korey, co-founder, Away Luggage
“I love an ugly-cute shoe and am always in backless loafers — I definitely have the cost-per-wear down on these Robert Clergerie mules. They’re perfect for slipping on and off while going through security and couldn’t be more comfortable, whether I’m walking across a city or sprinting across a terminal. They’re like the mullet of shoes: business in the front, party in the back. Just don’t forget to bring a pair of plane socks for the journey.” —Jen Rubio, co-founder, Away Luggage
“For good measure, I never leave home without my Birkenstocks. They are classic and fit me like a glove. They’ve become a staple of my wardrobe — I often find myself slipping them on every day when traveling. I usually also bring along my Philip Lim mule loafers because they can add sophistication to a business meeting and I can slide them on for dinner with friends. When it comes to sneakers, I go with the Allbirds wool runners. They’re incredibly comfortable and extremely lightweight.” —Ariel Kaye, CEO and founder, Parachute
“My go-to are Golden Goose sneakers, but I also just designed these Capybara Espadrille, which are Argentina inspired. They are incredibly easy to slip in and out, you don’t have to take them off at security and they are warm and soft.” —Sofia Sanchez de Betak, art director, fashion consultant and author of Travels With Chufy
“Sabah’s are the ultimate travel shoe because not only do they slip on and off with complete ease, but they are suitable for so many different climates. I wear the same pair to the beach that I wear in the winter with wool socks. Their supple leather molds to your foot making them super comfortable even after a long flight, and the unfussy design keeps them very lightweight. Not to mention they can elevate even the most basic stretchy pant to gypsy chic, and only look better the more global miles logged.” –Abra Boero, founder and creative director, Off Season Rockaway
“Lately, I’ve been noticing that everyone on my flights have been wearing some version of the Nike Flyknit Lunar 3. Seasoned travelers, from finance bros in half-zip Brooks Brothers sweaters to the Céline-sunglasses-wearing ladies toting Goyards, seem to have caught on to the fact that the Lunars aren’t just great gym shoes — they’re perfect for traveling. There’s no need to switch shoes once you arrive at your destination, either, especially if you’ll be bopping around on foot. The super-soft cushioning of the soles might be built for cross-training and 5Ks, but they’re incredibly comfortable for sightseeing, too.” –Jason Chen, Strategist senior editor
“I don’t get people who wear flip flops or anything without socks to the airport — that’s gross. And there’s a special place in hell for people who wear heels to the airport. I almost always wear my classic Stan Smith’s — comfortable and simple.” —Joe Grun, marketing manager, Butter Group
“The Converse Chuck Taylor Low Tops are my uniform shoe. I wear them to the office, to travel, to go out at night, and anything in between. I always have multiple pairs and will oftentimes bring more than one with me when traveling — but always in white.” —Josh Udashkin, founder and CEO, Raden
“My version of these Diadora sneakers are a collaboration with Patta. Those aren’t so widely available, but this is the same style. They’re snug, but also comfy so they’re easy to get on and off.” —Alex Chapman, associate brand manager, SWG
“Climate permitting I’ll fly in Havaianas because I love my feet to be open and breathe. Otherwise I’ll go with suede moccasins from U.K. brand Clarks. The Dakin Walk is timeless, incredibly comfortable and they breathe so well you almost don’t notice you have them on even on a long flight.” —Wilbert Das, owner, UXUA Casa Hotel & Spa
“I own eleven pairs of Mephisto’s. They began as walking shoes, or as the English call them, trainers. The same comfort technology is applied to their dress shoes. You can carry one pair for daytime hiking, and another pair for a nice dinner. I can comfortably walk back to my hotel at the conclusion of the evening.” —Navin Sawhney, CEO Americas, Ponant
“Sanuks are very comfortable traveling shoes, even though my feet seem to expand when flying. Sanuks are the only shoes that still feels fine.” —Chris Blackwell, owner, Island Outpost Jamaica
“I often wear loafers as they are easy to slip off for security checks and on the plane.” —Roeland Vos, CEO, Belmond
“I see tourists wearing Crocs, and a few pilots wearing black Danskos. No. Just, no. I wear a pair of Greats and combine it with TSA Pre-check. Comfortable, stylish, and the TSA agents give compliments but don’t make me take them off.” – Mike Arnot, founder, Owen & Fred
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best socks for traveling, dopp kits, rolling luggage, weekend bags, travel necessities, and portable speakers. We update links when possible, but note that deals can expire and all prices are subject to change.
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