Let’s throw out an old myth: Stylish, dressy shoes do not need to be uncomfortable. Sure, we might all rather be lounging in a pair of fluffy slippers at any given moment, but certain occasions like an office setting or a wedding call for more sophisticated attire. Still, there are plenty of dress shoes for women on the market that won’t force you to lug around your back-up sneakers or rely on the complimentary flip flops at a wedding reception.

Whether you’re looking for pain-free pumps, the best loafers to pair with a suit or the best flats for spring, we’ve rounded up the very best dressy footwear in every category — all with comfort in mind. You’ll find top picks that our editors reach for again and again from tried-and-true brands like Rothy’s and Everlane, as well as some new favorites (hello, Alohas) to add to the mix.

If you’re looking for a great pair of dressy pumps, we love The Heel by Margaux, a brand that topped our list of the most comfortable heels. And if you need a great suit or pair of pants to wear with your dress shoes, see our guide on where to shop for women’s workwear. 

Best comfortable pumps 

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  • The sustainable footwear brand’s ultra comfy pump has a roomy toe box and medium-height heel.

  • Whether paired with jeans or a gown, the 2.5-inch heels are so painless you’ll forget you’re wearing them.

  • These handmade Italian suede pumps have a sturdy block heel and light insole padding.

  • A cushioned footbed with arch support makes this leather block heel agreeable for daily wear.

Best ballet flats

  • Our editors swear by these leather flats (available in 9 colorways) which mold to your feet like socks.

  • Made from recycled materials and cushioned by Rothy’s signature In Love insole.

  • Available for under $100, these flats run large and have a heel cushion to prevent blisters.

  • These bejeweled satin d’Orsay slip-ons look equally great with distressed denim or a formal dress.

Best loafers

  • Everlane upgraded their fan-favorite loafer with a rounder toe for wiggle room and more flexible leather.

  • Try pairing these satin-lined smoking slippers with patterned tights for a dynamic and textured look.

  • This version of Gucci’s iconic horsebit loafers can also be worn as a loafer mule by folding down the collapsible heel.

  • Glossed leather gives this square-toe shoe with 3-inch heel an elevated look.

Best mules

  • The footwear brand taps podiatrists to develop shoes with built-in arch support, like these non-slip mules.

  • This pointed-toe slide brings the drama thanks to its luxe velvet upper and quilted satin insole.

  • Handmade with Napa leather, these narrow square-toed mules stand out with an artsy wooden heel.

  • This “Goldilocks” heel is just the right height for lengthening your leg without being too steep.

Best booties

  • These kitten-heeled moisture-wicking sock boots are a stylish alternative to rubber rain boots.

  • This special occasion stiletto bootie comes in neutral suede hues or an eye-catching gunmetal lame.

  • The trendy cowboy bootie gets an elegant upgrade with these metallic leather stunners.

  • The touch point of these leather platform block-heel booties are the plush, padded insoles.

Best sandals 

  • These festive strappy sandals are made with sustainable leather and have a 3.3-inch wide heel.

  • These ultra comfortable heels have a square toe platform and slim 3.5-inch block heels.

  • Five millimeters of plush foam padding and a 2.5-inch heel make these sandals superior in walkable comfort.

  • A lightly padded footbed adds cushion to these 3-inch ankle strap wedge sandals.

 


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