If you think a travel shoe that’s both stylish and comfortable is a myth, think again. We hunted down a selection of attractive, comfortable shoes that perform well on the move—whether you’re navigating cobblestone streets in Lisbon or making a quick dash to a lunch meeting in a museum café in Brussels.
Seasoned business travelers who tested these pairs had a few practical tips: choose natural materials like leather that breathe and give slightly with wear; never plan to break in brand-new shoes while traveling—make sure they fit comfortably at home before stuffing them in your carry-on; and remember that aside from cabin swelling, travel often includes uneven pavement and many stairs, so prioritize support and traction.
Women’s:
The Leather Street Shoe by Everlane
The Leather Street Shoe by Everlane ($135)
For travelers who like to pack light, this pair can cover meetings and long museum days without sacrificing comfort. Built with 100% full-grain leather uppers and leather footbeds, the Italian-made shoes feature hand-cut soles layered over four levels of foam for support. Gently ridged rubber outsoles provide reliable traction and cushioning for city streets. Available in grey and black, they offer a polished, versatile look that transitions easily from day to night.
© Off the Beaten Track
The Bee Cave by OTBT – Off the Beaten Track ($125)
When you want a little height without sacrificing comfort, the Bee Cave wedge sandals from OTBT’s Globe Trotter collection are a solid choice. With a relaxed, San Francisco summer vibe, they dress up or down depending on your itinerary. Leather uppers with matching stitching are accented by metal buckles, and the leather-covered heel and cork footbed deliver excellent shock absorption and cushioning. Offered in black, gold, and pewter, they’re ideal for travelers who want style plus steady support.
Men’s:
Mephisto Irwan Moccasin
The Irwan by Mephisto ($299)
This refined moccasin, available in black and dark brown, blends classic style with comfort-focused engineering. Smooth leather uppers and leather linings sit on durable rubber soles, while built-in heel shock absorbers and removable insoles with the brand’s Soft-Air Technology reduce impact. The Irwan pairs seamlessly with a casual suit or jeans and a cashmere pullover, delivering a polished look without compromising on cushioning and support.
© Pitman Run
Pitman Run by Clarks ($140)
The Pitman Run from Clarks’ Tor collection combines modern casual style with proven comfort technology. Constructed with soft textile uppers—30 percent wool knit—and suede mudguards, this lace-up features stylish perforations and a clean silhouette suited to travel. Ortholite cushioning, EVA soles, and ExtraLight construction deliver flexibility and lightweight support, while strobe stitching adds durability. These sneakers hold up well to long days of walking and maintain the comfort Clarks is known for.
Choosing the right pair comes down to material, fit, and the kinds of surfaces you expect to encounter. Opt for leather or breathable textiles, ensure a comfortable fit before you travel, and favor soles with good traction and cushioning. With those priorities in mind, you can find stylish, travel-ready shoes that keep your feet happy mile after mile.