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Picking out the perfect outfit can be a challenge under the best of circumstances. So when the weather doesn’t cooperate or you're about to commute on foot, you can feel...extremely frustrated. That's why we put together this list of shoes that are comfortable, supportive, and can stand up to less-than-ideal conditions — all without ruining your outfit.
Water-friendly slides that are chic enough to wear out…
If you’re looking for slip-on sandals that feel light as air but can hold up against torrential downpours, these Big Buckle sandals from Birkenstock are our pick. Like most Birks, they’re contoured to fit your foot just right — but these are made of EVA, so they’re actually waterproof. The eight tones are muted and versatile, so you can really wear these anywhere.
All-white sneaks with old-school flair…
These Reebok Club C 85 Vintage sneakers simply won’t stop popping up all over our social feeds. We love that they’re unisex, insanely comfortable, and add a hint of nostalgia to any daytime look.
Closed-toe sandals with built-in arch support…
Two editors tried out DREAM PAIRS for the first time and loved their shoes’ thick soles, thoughtful designs, and wallet-friendly price points. These closed-toed flats are a great option for when you want to wear sandals but don’t want to expose the toes.
Mary Jane flats with major sneaker energy…
If you’re going for the ballerina look but navigating arduous terrain (or just walking a lot), these Adidas Mary Janes will be your new best friends. They have the comfort of Adidas sneakers (thank you, Cloudfoam Comfort footbed) and the classic design of a ballet flat. It’s one of our favorite day-to-night options.
Woven mules if you’re over basic flats…
These Mi’i mules from OluKai are inspired by traditional Polynesian lauhala weaving techniques and the feeling of bare feet on wet sand. They’re super supportive and pair well with shorts, jeans, and dresses alike, making them the perfect shoe to pack while traveling.
Tall black boots you can wear year-round…
These simple, yet sophisticated knee-highs have a thick sole that will give you the height of a 2-inch heel without discomfort or knee pain. They’re the LBD of footwear, especially on rainy days. Wear them with a lace skirt or slip dress for date night, or over jeans for a more casual look.
Classic Sperrys that never go out of style…
We heard 2026 is the new 2016, and that means breaking out our tried-and-true Sperrys. They’re always a classic, but they come in some new prints and colorways (like cottagecore florals and leopard print) that make them feel fresh again. They're also functional, thanks to a leather exterior and tractioned outsoles.
A cuter version of our favorite “Dad shoe”...
No one knows practical, durable footwear like the dads in our lives. These New Balances would make him proud, but these colorways (like lavender and butter yellow, or muted tan and blue) feel current. They’ll last for years and pair with more items in your closet than you think.
A cloud-like running shoe that’s sleek and supportive…
We’ve been big fans of Brooks for a while, and the new Hyperion Max 4 doesn’t disappoint. They’re surprisingly lightweight and offer maximum support for walking or running, and the sleeker silhouette is easier to style than chunkier versions. If you see us with a little extra pep in our step, it’s probably because we’re wearing these.
The most comfortable strappy sandal…
For near-clinical levels of comfort, we turn to Dr. Scholl’s. These sandals are inspired by their bestselling Time Off sneakers, but these have adjustable ankle straps and a slight heel take it to the next level.
Loafers worthy of a princess…
If Docs are good enough for Mia Thermopolis, Queen of Genovia, they’re good enough for us. We love these loafer versions for a classic ‘90s look with jeans and an oversized button-down, or with lacy socks and a maxi skirt.
A chic Mary Jane you’ll wear well into fall…
Like all Clarks, these Mary Janes are designed to feel broken in right out of the box. They’re comfier than most flats we’ve tried, but the faux-croc finish gives them an elevated feel.
Combat boots that make a statement…
Combat boots aren’t just for winter. These ankle boots are an easy way to add edge, and the white colorway makes them appropriate for any season. They’re a true all-weather staple, and (bonus) they’re under $45.