1 of 20 Courtesy of Aerosoles
Aerosoles ($59) provide 360 degrees of comfort with their flexible bottoms, memory foam insoles, and suede lining.
2 of 20 Courtesy of Clarks
Save precious suitcase space with a shoe that can take you from day to night. This style from Clarks ($90) pairs well with jeans, skirts, and beyond.
3 of 20 Courtesy of Amazon
Just what the doctor ordered: a timeless loafer with a memory foam insole from Dr. Scholl’s ($65)—it’s as comfortable as it is classic.
4 of 20 Courtesy of Adidas
Adidas’s Stan Smith ($75), the sneaker du jour, gets major points for being cool and cushy. Plus, the versatile all-white style pairs well with jeans, skirts, or shorts.
5 of 20 Courtesy of Amazon
The supportive rubber outsole and ABS—a really strong synthetic rubber—heel on this Born Khate sandal ($55) is perfect for pounding the pavement in style.
6 of 20 Courtesy of Amazon
Cole Haan’s ZERØGRAND slide sandal ($150) touts the same cushioning technology as the brand’s popular loafers. It’s a chic option for warm-weather destinations.
7 of 20 Courtesy Naturalizer
This leather loafer from Naturalizer ($89) touts multiple elements of comfort—extra cushioning, a flexible non-slip sole, and breathable lining— for a full day on your feet.
8 of 20 Courtesy of Repetto
Forget walking; try pirouetting through your trip in Repetto’s ballerina flats ($295), which are made with the same stitching technique as the brand’s ballet shoes, making them ultra-flexible.
9 of 20
Asics, known for running shoes, brings dependable support to a lightweight sneaker ($65).
10 of 20 Courtesy Bernardo
This Bernardo suede ballet flat ($159) has a no-slip leather outsole, padded insole, and crisscrossed elastic strap for active ankles.
11 of 20 Courtesy Reebok
A seamless neoprene upper makes Reebok’s Skyscape ($20) easy to wear and even easier to pack.
12 of 20 Courtesy of Pikolinos
Before your toes hit the sand, pamper your feet in gel-and-foam-padded leather sandals from Pikolino ($160).
13 of 20 Courtesy of Tevas
Teva’s super-packable crossover strap sandals ($90) have an ample footbed and featherlight foam soles that are still durable.
14 of 20 Courtesy of Soludos
For the ultimate cheeky weekend accessory, see cult espadrille brand Soludos’s collaboration with quirky artist Jason Polan. The limited-edition shoes come in both black and sand, and are embroidered with a pair of winking eyes ($75).
15 of 20 Courtesy Reef
Summer strolls call for a breathable espadrille. Reef’s version ($70) provides arch support and a soft footbed.
16 of 20 Courtesy Rockport
Despite the classic aesthetic of this Rockport shoe ($67), the style is surprisingly rich with features. Built-in sport technology provides shock-absorption, ample cushioning, and lots of support.
17 of 20 Courtesy Keds
All-American brand Keds ($35) puts fun, colorful prints onto rubber-soled, lace-up sneakers.
18 of 20 Courtesy of Tod's
Pebbled driving soles soften the step while pale pink leather raises the trend quotient on this Tod’s moccasin ($445).
19 of 20 Courtesy of Toms
This slip-on from TOMS ($59) will take you from seaside to sidewalk with a rubber outsole, breathable linen upper, and comfortable insole.
20 of 20 Courtesy of Tomas Maier
You will forever find well-made flats from Tomas Maier, the designer who vows to never make a heel. Here, his take on sleek leather sneakers ($480).
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