None

18 Most Comfortable Travel Shoes

October 25, 2016

Subscribe for Access


Travel can take many forms, from hiking glaciers in Patagonia to riding horses in the High Sierras. But whether you’re getting there by plane, train or pack animal, having comfortable footwear is essential to enjoying the journey and the vacation as a whole.

After all, cozy flats will get you through security and into the first-class lounge, but for hours of ambling along cobblestone streets, you need rugged slip-ons or stylish boots ready for action. We’ve rounded up 18 shoes for men and women that will put a spring in your step as you explore the world.

LOW-PROFILE

Travel can take many forms, from hiking glaciers in Patagonia to riding horses in the High Sierras. But whether you’re getting there by plane, train or pack animal, having comfortable footwear is essential to enjoying the journey and the vacation as a whole.

After all, cozy flats will get you through security and into the first-class lounge, but for hours of ambling along cobblestone streets, you need rugged slip-ons or stylish boots ready for action. We’ve rounded up 18 shoes for men and women that will put a spring in your step as you explore the world.

LOW-PROFILE

For Him: Toms

There are many reasons these canvas slip-ons are so popular: The classic Alpargata style feels perfectly comfortable through an entire day of wandering; they are available in myriad colors and materials; and the price point makes them easy to stock up on (which of course, means more shoes for needy children with their one-for-one promise). We like the distinguished Charcoal Herringbone Classic option ($55).

For Her: Tieks

Tieks’ distinctive blue-soled shoes combine style and comfort for those constantly on their feet. The rubber bottoms and cushioned instep provide more support than your average ballet flat. And while elegant enough to go from day to night, the shoes fold for purse storage in case you need to switch to your red soles. Available in supple leather or vegan fabric, shiny metallics or muted mattes, the rich burgundy ($175) is a great color for fall.

URBAN COMFORT

For Him: AllBirds

Since maxing out a 2014 Kickstarter in just five days, AllBirds has made a business of beautifully simple merino wool kicks. The secret of these Kiwi creations, which come in a variety of colors for men and women, is a machine-washable superfine wool that stays soft, wicks away moisture, keeps odor at bay and regulates temperature. Given the company’s dedication to keeping its product natural and sustainable, the Wool Runner ($95), is a shoe that feels good in more ways than one.

For Her: Sperry

Made popular by the nautical adventures of the Kennedy family in the ’60s, Sperrys are the epitome of practical prep. With wet-dry traction and hand-sewn construction, the Gold Cup Original Boat Shoe ($111.97) adds a touch of luxury with ultra-soft lambskin linings and memory foam.

FUZZY BOOT

For Him: Tod’s

If you want a VIP lounge for your feet, Tod’s is the obvious choice. Though this Italian luxury brand is known for its moccasins and driving shoes, it’s hard to imagine a more plush shoe experience than the Suede Lace-Up Ankle Boots ($565), with exquisitely crafted suede.

For Her: UGG

The popular but polarizing surfer boots of 2003 have evolved with the times yet remain some of the most comfortable shoes available. With water- and stain-resistant styles and the signature fluffy wool, UGGs can keep your feet cozy on long-haul flights or on chilly walking tours. Go with the Classic Cuff Mini ($160) in navy for a boot with several styling options.

VERSATILE BOOT

For Him: Billy Reid

Award-winning designer Billy Reid marries a down-home Southern aesthetic with luxe materials. The butter-soft calfskin leather and contemporary piping details on the Short Anderson Boot ($495) make for a dapper style that can cross continents.

For Her: Frye

Since 1853, this iconic American heritage brand has focused on quality leather goods. Frye boots fit beautifully, have a universal appeal and stand the test of time (in terms of both fashion and durability). For a classic riding boot that can go from casual to sultry, try the Jackie Button ($418) with hand-burnished antique leather and an elegant heel.

TREKKING SHOE

For Him: Merrell

If your preferred style of vacationing is a little more rugged, turn to top hiking-boot maker Merrell, whose products are tough and durable yet lightweight and supportive. The popular Jungle Moc waterproof trekkers ($80) have the features of a hiking boot in a more casual slip-on.

For Her: Ahnu

Consistently ranked among the most comfortable trekking shoes with no break-in time, Ahnu’s Montara II WP ($135) is a breathable, lightweight hiker designed to help you keep your footing in the rockiest terrain (the company is appropriately named after the goddess of balance). Partnering with charitable organizations, Ahnu ensures that its supply chain is ethical and beyond reproach. Plus — not that it should matter when talking about such highly rated hiking boots but — they come in very pretty colors as well.

SLIP-ONS

For Him: Clarks

Thanks to almost 200 years of shoemaking, Clarks has perfected the classics and continues to innovate. Its latest line, Cloudsteppers, are incredibly light, breathable and flexible to ensure comfort in every step. The Votta Free ($59.99) slip-on provides cushioning for wherever your travels take you.

For Her: Vince

With minimalist design and high-end materials, Vince is the epitome of everyday luxury. These leather sneakers ($195) are a polished take on a slip-on, with subtle details that make it anything but ordinary.

CITY SHOE

For Him: Cole Haan

The 89-year-old Cole Haan brand has made innovation a central tenet of its Grand Revolution line, essentially combining dress-shoe styling with running-shoe comfort. The Washington Grand Laser Wingtip Oxford ($280) touts a complete redesign of the classic oxford, making it sleek, lightweight and cushioned.

For Her: Repetto

A Parisian classic since 1947, Repetto’s ballet-inspired shoes still exhibit careful attention to stitching and quality. These Fado Oxfords ($375) offer stability with a touch of elegance.

STYLISH SANDAL

For Him: Teva

If your feet yearn to be free but you can’t exactly go barefoot, look no further than Teva. Its sporty, sturdy sandals will support your feet through the roughest circumstances. After all, the original design was spawned from rafting in the Grand Canyon back in 1984. The Katavi style ($65) supplements rugged utility with a touch of plush suede.

For Her: Birkenstock

Known for its signature contoured footbed that molds to the shape of your foot, this flower-child favorite has matured over the years. The popular Mayari Antique Lace sandal ($94.95) shows a delicate side of Birkenstock, with a strappy toe loop and pearled shine.

SEXY SNEAKERS

For Him: Common Projects

A highly sought-after brand for luxury sneaker aficionados, Common Projects is the collaboration of American design and Italian craftsmanship. A choice example of its sleek minimalist aesthetic is these high-top sneakers ($420), with all-over suede.

For Her: Vans

Widely known for its comfort, Vans has finally come out with a more grown-up version of the skate shoe. Meet the vintage-inspired Leather UA Reissue ($75) in Whisper Pink Gold.

Get Inspired for Your Next Adventure

Register to sample:

  • One-of-a-kind itineraries
  • Inspirational travel articles
  • Free e-newsletter from our editors
All fields are required.

TAGGED
By Erin Russell Hideaway Report Contributor

Contact a Travel Advisor
Hideaway Report members have access to travel advisors at our partner Andrew Harper Travel. Learn More
Call Andrew Harper Travel:
1 (800) 375-4685
OPEN M-F 8AM-6PM CST

Follow Us