One-Shoe Trip? These Are the Best Pairs That Do It All

Here’s the one pair to consider for every travel demand, whether you’re looking for day-to-night versatility or a weather-appropriate workhorse.

The biggest one-shoe travel mistake you can make is opting for clunky rain boots—even if you’re heading somewhere perpetually rainy. There are many more versatile options than the traditional Wellington, which is heavy and often lacks insulation.

Lower-cut waterproof options with a sleek design and warm lining are best: Tretorn’s Lina winter rain boot is one of the warmest I’ve found. My personal favorite for day-to-night waterproof style is Kate Spade’s Sedgewick rain boot. The Chelsea cut of these boots makes them more attractive than the average rain boot, and the style is unisex: Men’s options include Tretorn’s Gus Rain Boot.

Warm destinations are the easiest places to pack a light bag for, but bringing two types of sandals or slip-ons can feel necessary if you’ll be doing both active and smart-casual activities. There are, however, versatile options that fit both occasions thanks to Tevas, which are newly on-trend and still durable.

Chic utilitarian options like the Teva Midform Universal Geometric or Teva Midform Universal Leather are virtually foolproof for women going from long walks to dressing up at dinner. There are also plenty of men’s Teva sandals to choose from, but waterproof, closed-toe options like the featherweight Arrowood 2 Waterproof or Teva Wilder are worth considering if sandals won’t do for your dinner reservations.

In the transitional weather of fall and spring, ankle booties are key to staying warm while still being able to walk comfortably, thanks to a little more insulation than the average walking shoe. Clarks is a reliable brand for walking shoes with support, and has stylish ankle boots like the Maypearl Ramie for women and various desert boots for men.

Related:9 Stylish Boots You Can Walk In

For strictly casual trips, all you need is the right pair of stylish sneakers. Traveler-favorite Allbirds are sustainably made and come in an array of styles and materials. Options include lightweight, breathable Tree Runners for men and women—or choose a warmer merino wool sneaker, also available in both men's and women's versions. For something a little more polished, Johnston & Murphy Tamara Perf sneakers stand out in a crowd.

If nightlife or nicer restaurants (the kind with a no-sneakers policy) are on your must-do list, walking shoes that look like anything but are ideal for transitioning from day to night. For women, Johnston and Murphy’s Cassandra sandals do it all in warmer weather; for a closed-toe option, Everlane’s Day Glove flat molds to your feet while staying supportive, breathable, and versatile.

For men, Timberland’s Cross Mark Oxford sneakers (SmarterTravel’s Editors' Choice winner for best new men’s travel shoe in 2018) combine a lightweight rubber cushion with premium leather to easily camouflage as dress shoes.

Related:5 Travel Wear Pieces That Go from Day to Night

Winter weather doesn’t have to mean putting up with heavy snow boots. There are plenty of warm, waterproof options that are also surprisingly lightweight and stylish.

Cougar Shoes are a good go-to brand for snow and waterproof everything, from night-appropriate heeled boots to snow bunny-approved “Winter Sneakers” that ingeniously pair the lightweight idea of sneakers with winter features like waterproof anti-slip soles and warm insulation. Cougar Shoes also mixes up men’s snow options with the sleek Crowley Winter Chelsea Boot.

Related:Winter Boots for Walking

Don’t bother wearing your hiking boots the whole active trip—even if you think you’re being smart by wearing them on the plane. Heavy hiking footwear could be replaced by Merrell’s MQM Flex GTX Men’s Hiking Shoes, which are also available for women. They’re lightweight (14 ounces) and breathable like a sneaker, but still waterproof and supportive, and they even have anti-slip outsoles like a hiking boot.

Business travelers don’t have to travel in comfy sneakers and then change into restrictive dress shoes anymore—it’s easy to find a pair that can do both comfort and business-appropriate style. Johnston and Murphy has men's and women’s options worth investing in as your one-shoe travel companion, like the Prentiss Plain Toe leather sneaker for men, and the Elaina leather slip-on for women.

• Editors' Choice Awards: Best New Travel Shoes for Men
• Editors' Choice Awards: Best New Travel Shoes for Women
• 12 Amazing Waterproof Shoes for Spring Travel

SmarterTravel’s Shannon McMahon writes about all things travel. Follow her on Instagram @shanmcmahon.