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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of braided sandals with a supportive chunky heel proves that you *can* dress up virtually anything: even your favorite band tee and broken-in pair of jeans.
2. A mesh slip-on shoe because, honestly, who has time for laces? These shoes are made from mesh, meaning they'll conform to your foot like a glove while still remaining exceptionally breathable.
3. A pair of structured Clarks flip-flops with footbed cushions, so you won't come away from your day at the beach with aching soles.
4. 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.
5. A pair of slide sandals that feel like walking on clouds. These sandals have an ethylene vinyl acetate sole, which just so happens to be the same material from which spongey running shoes are made. These'll give you all the comfort of supportive, bouncy shoes while also amping up your style with a very on-trend look!
6. 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!
7. 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.
8. 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).
9. 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!
10. A pair of chic sandals that you can wear anytime, anywhere — whether you're off to a meeting, brunch with friends, or getting your wardrobe ready for wedding season!
11. 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!)
12. A pair of wedge sandals that feel like actual clouds, despite the fact that they *look* like ultra-chic uncomfortable shoes. I wore these while on a trip to Croatia a few summers back, and they SAVED my feet as I trotted all day along ancient Roman (aka, marble) streets!
13. 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!
14. A cute pair of boat shoes that *feel* like sneakers while helping you nail your coastal grandma aesthetic.
15. A platform heel with a woodgrain-printed sole, since, yes, wooden soles are *so* comfortable once they're broken in, but can be a bit hard to get used to if you typically reach for shoes with cushioned soles. These shoes form to your feet and feel like air while giving off the vibe of yeah, I can totally walk around in heels for hours.
16. A very cute and trendy mesh flat that is everything you've ever wanted in a shoe — style and breathability! You can wear these with knee-high socks for a funky spin on the classic coquette shoes-and-sock combo, or wear them alone to show off your pedi!
17. A pair of basic round-toe pumps with a kitten 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.
18. A pair of Hoka Bondi 8 running shoes that I wear pretty much everywhere — from my daily runs to long (and I'm talking 10,000+ steps) walks through the city. These offer a ton of support and are very roomy and breathable!
19. A soft rubber sole slipper so you can enjoy the warm, cozy feeling of socks with the protection and grip of a traditional slipper.
20. A sparkly wedge sandal that allows 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!)
21. A pair of cushiony Reebok sneakers so you can have a pair of reliable shoes for running errands, walking the dog, or even just doing chores around the house. And as a bonus, they look ultra cute! How can you go wrong?!
22. A pair of scrunch ballet flats that conform to your feet while you serve your best #balletcore look. They're also quite handy to keep in your bag when you know your feet won't last all night in stilettos.
23. A wedge gladiator sandal for folks who prefer closed-toed shoes, but still want a bit of ventilation. These sandals come with adjustable ankle straps to ensure a proper fit that conforms to your foot.
24. A pair of big buckle Birkenstocks that 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.
25. A pair of Anne Klein wedge pumps that will 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.
26. A pair of faux-leather strap sandals that will look equally good with casual and dressed-up 'fits. They're even engineered to absorb shock while walking, making them perfect for those living in big cities.
27. A pair of Crocs you can wear around town for a casual, errand-running shoe. Want to take it up a notch? Throw these into sports mode for those extra-long shifts where you'll be on your feet all day.
28. And 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.
The reviews for this post have been edited for length and clarity.