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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of basic round-toe pumps with a mid-sized heel that'll look fancy at special events while being comfy enough to wear all night long — yes, that means buh-bye flip-flops that you bring to every wedding.
2. A pair of Adidas Cloudform running sneakers because training for a race is challenging enough — make it at least a bit less painless with these lightweight, breathable, and cushy sneakers.
3. A soft rubber sole slipper so you can enjoy the warm, cozy feeling of socks with the protection and grip of a traditional slipper.
4. A cushy pair of slides you'll gladly wear absolutely EVERYWHERE, whether you're sporting them to waltz around the house or putting them on to run your weekly errands.
5. A sparkly wedge sandal allowing you to bring a touch of glam to your 'fits without having to fortify yourself from blisters. (Goodbye, trying your hardest to hide bandages underneath dressy shoes!)
6. An espadrille wedge that absorbs shock with its platform-like sole and keeps the foot in place with its ankle strap. All while looking cute enough to wear with any dress in your vacay wardrobe.
7. A pair of braided sandals with a supportive chunky heel proving that you *can* dress up virtually anything: even your favorite band tee and broken-in pair of jeans.
8. A mesh slip-on shoe because, honestly, who has time for laces? These shoes are made from mesh, meaning they'll fit your foot like a glove while still remaining exceptionally breathable.
9. A pair of big buckle Birkenstocks — these form to your foot over time without compromising on comfort. And those buckles aren't just for style — they're adjustable, which is a BIG plus for people with high arches or bunions.
10. Or a cozy pair of waterproof Birkenstock sandals that'll work great as house shoes or chic headed-around-town shoes when the moment strikes!
11. A black pointed-toe pump because it's the type of basic, versatile shoe that belongs in every wardrobe. The footbed forms to your foot, while the leather stretches easily for a perfect fit. I have these shoes, and I can easily spend hours in them without feeling an ounce of pain.
12. A quilted slip-on shoe with memory foam insoles to make it feel as if you're stepping on a fluffy pillow with each stride. Pair these with your favorite leggings for times when you want to be comfy while running errands, but you also want to look put-together.
13. A handmade pair of leather huarache sandals you'll *definitely* want to collect in every hue. These shoes hold onto your ankle to provide support during long walks and even have a platform that adds cushion!
Macarena Collection/Etsy
Promising review: "Shoes are so cute and comfortable. I bought the black and I actually want to get other colors. Perfect for skirts, summer dresses, capris, and jeans. I will take them when I return to Italy. Love them!" —Melissa McCormick
Get it from Macarena Collection on Etsy for $46.42 (originally $61.90; available in sizes 5–10 and in more colors/styles here).
14. A pair of low wedge flats, because finding shoes that accommodate wide feet can be tricky — throwing a high arch into the mix can make things even trickier! I personally have wide feet with a high arch, and I always recommend a roomy shoe with just a liiiiiittle bit of wedge for extra support!
15. A pair of chic sandals you can wear anytime, anywhere — whether you're off to a meeting, brunch with friends, or getting your wardrobe ready for wedding season!
16. A pair of chunky sandals for helping you release your inner Daria. These are perfect for anyone who wants to serve '90s vibes but needs something less intricate to emulate the decade. These shoes are super simple to throw on and add an immediate edgy (and cute!) touch to your 'fit.
17. A patent leather loafer, because what's better than wearing sneakers to the office? Wearing work-appropriate shoes that feel as comfortable as sneakers, that's what!
18. A pair of Anne Klein wedge pumps that distribute pressure evenly throughout the entire footbed — not just on the heel or sole. This is great if you want an elevated look with a cozy shoe feel.
19. A pair of braided sandals if you need something that will bring you everywhere during your upcoming vacation while slotting seamlessly into your carry-on bag. (I'm looking at you, light packers!)
20. A pair of Western booties to prove that tying together a chic outfit doesn't have to mean contorting your toes into an uncomfortable boot. What's more, these booties have a handy zipper, which is excellent if you often struggle (same — wide feet problems) to casually slip into most cowboy boots.
21. And a braided thong sandal with an adjustable buckle so that you can wear gladiator sandals that won't feel constricting or uncomfy after a few hours. Hurray for style and comfort!
22. A pair of Sperry sneakers essential if you're increasing the coastal grandmother aesthetic in your wardrobe. These shoes, plus an oversized button-up shirt, has ~going to Cape Cod this weekend~ written all over 'em.
23. Or a cute pair of boat shoes that *feel* like sneakers while helping you nail your coastal grandma aesthetic.
24. And a pair of sporty sandals with adjustable straps, because your everyday sandal should look good *and* feel comfy! The cushioned sole means you can wear these during long walks with your pup or while running errands at the grocery store.
The reviews for this post have been edited for length and clarity.