Comfy footwear to bring on your next vacation
Choosing shoes for a trip is always a bit of a balancing act. You want something comfortable enough for all the walking that inevitably happens but also versatile enough that you are not packing a different pair for every outfit.
To narrow things down, I asked our team members which shoes they actually like traveling in—and, more importantly, which ones have proven comfortable after hours on their feet.
The result? A mix of sneakers, sandals, and jelly shoes suited to everything from city breaks to tropical getaways.
Converse Chuck 70 X
The Chuck 70 X is a good option for trips where you want one sneaker that can work across most of your wardrobe. It keeps the familiar Chuck shape but gives it a more elevated finish through premium materials, dual-star detailing, an updated leather patch, and subtly aged touches.
That balance makes it especially useful on trips: casual enough for long days walking around the city but still clean enough to wear with trousers, skirts, or dresses for dinner. It also works across different types of destinations—from cooler city breaks with denim and layers to warmer trips where you might wear it with shorts or lighter pieces.
Puma Tacklette
The Puma Tacklette is for days when a chunky shoe feels too much. Its low-profile silhouette sits somewhere between a Mary Jane, ballet flat, and sneaker, giving it a sleeker look without leaving all the cushioning behind.
A buckle strap holds the foot in place, while the streamlined shape slips easily into luggage. It is especially handy if you tend to wear skirts, dresses, or wide-leg trousers on vacation but still need footwear that can keep up with a day spent out and about.
Melissa Margot in Brown
For relaxed city dressing or somewhere tropical, the Melissa Margot brings the ease of a jelly shoe without the hard plastic feel you might expect. Its Melflex® construction gives the shoe a softer, more flexible feel, with a sole that has plenty of give and a strap that stays gentle against the skin instead of digging in as the day goes on.
The brown shade also makes the matte finish surprisingly easy to style with linen, denim, neutrals, swimwear, and breezy dresses.
Keen Jasper
The Keen Jasper makes more sense when the itinerary extends beyond cafés and shopping streets. Its climbing-inspired design includes laces that run farther toward the toe, giving you more control over the fit, while the roomier forefoot leaves space for the toes to spread.
The suede material softens its outdoorsy appearance, so it can still be worn around town without looking like dedicated hiking gear. It is a solid option for vacations that might include parks, countryside stops, or light trails alongside your usual sightseeing.
Adidas Ultraboost 20
If your vacation plans tend to involve serious mileage, the Adidas Ultraboost 20 brings plenty of cushioning without feeling overly rigid. Its Boost midsole softens each step, while the knit wraps closely around the foot and moves with it rather than fighting against it.
That makes it particularly suited to sightseeing days, airport transfers, and itineraries where sitting down is mostly reserved for meals. The streamlined runner shape also blends easily into casual travel dressing—from leggings and shorts to wide-leg trousers.
Asics Gel-1130
The Gel-1130 is a stronger choice for anyone who prefers more structure underfoot.
Originally designed as a stability running shoe, it combines heel cushioning with additional support through the midfoot, which can feel especially welcome several hours into the day. Mesh panels add breathability for warmer destinations, while its retro runner silhouette keeps it from looking purely performance-driven.
Wear it with loose tailoring, denim, shorts, or a longer skirt when you want support without sacrificing the outfit.
Renegade Folk Woman Soft Insoles
One of our team members wore Renegade Folk’s Woman Soft Insoles around Bangkok and clocked roughly 12,000 steps in them, which says plenty for a flat sandal. The cushioned footbed makes long hours on your feet more manageable, while genuine leather straps and insoles feel soft against the skin, and a rubber outsole adds grip.
The gold finish also gives it more range than a basic daytime sandal, moving easily from linen and shorts to something dressier at night. Its slim profile is another plus when every bit of suitcase space counts.
Keen Newport H2
For beach days, waterfalls, boat rides, and anything likely to involve wet feet, the Newport H2 fills the space between a sandal and a more protective outdoor shoe. Its open construction allows water to drain, while the covered toe offers extra protection around rocks or uneven ground. A grippy outsole also gives you more traction on slick surfaces.
Instead of bringing separate footwear for water activities and the rest of the day, this is one you can keep on once you head back into town.
