Long before the pandemic took away my will to wear anything remotely uncomfortable, my foolproof first date outfit was sneakers with a dress. In the words of 2018 Allie, "I think making awkward small talk while being strapped into painful shoes is actually one of Dante's circles of hell." I still stand by this statement, as pairing sneakers with a dress makes for a heavenly, put-together fit for first dates and otherwise.
For starters, lacing up a pair of sneakers with a dress looks stylish without overdoing it. TBH, any outfit that allows one to both wear comfy shoes and not wear pants is, in my humble opinion, *chef's kiss.* Many sneakers are also better for feet compared to sky-high heels or flat sandals that don't provide any arch support. (Although contrary to popular opinion, there are many podiatrist-approved sandals that give your arches some sweet relief.) Lastly, sneakers are straight-up more versatile to do things in; whether it's commuting to work (if you're back doing that), walking the dog, or meeting friends for dinner, sneakers with dresses are just more comfortable, plain and simple. And if you don't believe me, check out the sneakers below that will convert you into a full-fledged, dress-with-sneakers believer.
8 comfy sneakers that pair well with a dress
Available sizes: women’s 5-10, in half sizes
Sneakers with a dress are a classic, but if they’re white sneakers? Arguably even more timeless. For that simple, chic look, you can’t go wrong with Thousand Fell’s minimalist, “ride-or-die” sneakers. Made from ridiculously comfy, sustainable materials, you will never, ever want to Thousand Fell’s cute kicks off. And you don’t have to—not even when you’re playing dress up. The effortless, sleek design looks adorable with all sorts of dresses. What’s more, they’re breathable, stain, and odor-resistant, too, which means they’ll stay fresh n’ clean no matter what sort of adventures you get into. Seriously—the brand apparently tests them for durability, and they last a whopping 2.4 million steps before they get tired. AKA, they last a lifetime.
Available sizes: women’s 5-12, in half sizes
If you prefer a chunkier sneaker with a bit more body, add the Nike Air Force 1 ’07 to your cart. Another timeless style, the Nike Air Force 1s have that iconic, sporty look that looks just as good on the basketball court as it does commuting to work or throwing back drinks at Happy Hour. Since it was designed for hoops, it’s got plenty of support, especially in the ankle and padded collar. But don’t worry about it weighing you down—these sneaks are as light and breezy as the dresses you pair ’em with.
Available sizes: women’s 5-11, in half sizes
For a beachy, laid-back vibe, swap your Reef flip flops for a pair of Reef sneakers, which are just as comfy as their open-toe’d counterparts. The Sunset Shoe is perfect for summer nights when you want a casual sneaker that’s supportive and protective and still is fashionable. The upper is made from an airy linen that’s as cool as an ocean breeze, while the soft-as-a-cloud footbed comes with built-in arch support and heel cupping. The espadrille detailing around the outsole and creamsicle orange laces are a nice touch, too, and elevated minimalist dresses.
Available sizes: women’s 5-13, in half sizes
Prefer the lace-free life? Get a pair of Rothy’s Original Slip On Sneakers, which are undoubtedly some of the best slip-on sneaks out there. Not only are they adorable, they’re eco-friendly and good for the planet as their upper is made from recycled plastic water bottles. But they’re washable, too, meaning if they get dirty or muddy, you can pop them in the washing machine and they’ll come out looking good as new. Bonus: They don’t stretch. While other slip-on sneakers inevitably stretchy out, these hold their shape, so you won’t have to worry about them falling off your feet down the line.
Available sizes: women’s 8-13, in half sizes
Aether is a go-to for sleek, stylish pieces that look at home in the city, but are functional for outdoor adventuring. These sneakers are their first sneakers for women, and they come in both black and white. Thoughtful detailing is a staple for the brand, and what stands out about these is that the insole is made with the same shock absorbent, impact protective material that their motorcycle gear is made from.
Available sizes: women’s 5-15, in half sizes
Found: the perfect chunky-but-not-too-chunky sporty sneakers. They’re a little clompy, which gives a nice contrast to ultra-flirty dresses. Since they’re made by Hoka you know they’re a treat for feet as they’re designed to be supportive, plush, and shock-absorbing with every step. Choose from versatile neutrals like gray and white, or add a splash of color to your ‘fit with the baby blue (“country air/bit of blue”), chocolate brown (“cappuccino/cork”) and sea foam (“smoke green/celadon tint”).
Available sizes: women’s 5-15, in half sizes
These shoes were designed for skating, but even if you’ve never even set foot on a skateboard, you can still benefit from the memory foam insole and sticky grip outsole. The simple design and seven neutral color combos make these very wear-with-anything-able. Every purchase of Cariuma shoes plants two trees.
Available sizes: EU 36-43
Part of a collaboration between M.M.LaFleur and Koio, these sneakers, which are handmade in Italy, are simultaneously dressy and chill. They’re simply begging to be paired with that dress in your closet you love but can’t figure out how to style. The sneakers come in three monochromatic colors: azalea, white, and gray.
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