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 for pairing with a suit, or the best flats for summer office days, 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, Allbirds and Everlane, as well as some new favorites (hello, Alohas) to add to the mix.
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Best comfortable pumps
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The sustainable footwear brand’s ultra comfy pump has a roomy toe box and medium-height heel.
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Whether paired with jeans or a gown, the 2.5-inch heels are so painless you’ll forget you’re wearing them.
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These handmade Italian suede and leather pumps are built to last.
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A cushioned footbed with arch support makes this leather block heel agreeable for daily wear.
Best ballet flats
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Insider editors swear by these leather flats (available in 10 colorways) which mold to your feet like socks.
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Made from Rothy’s signature recycled material, it also has a vegan, carbon-free rubber-and-TPU sole.
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The $100 flats offer a sleek silhouette that is breathable, flexible, and supportive.
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These bejeweled satin d’Orsay slip-ons look equally great with distressed denim or a formal dress.
Best loafers
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Everlane upgraded their fan-favorite loafer with a rounder toe for wiggle room and more flexible leather.
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Despite the 2-inch chunky heel, these chainlink-embellished loafers are so easy to walk in.
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This version of Gucci’s iconic horsebit loafers can also be worn as a loafer mule by folding down the collapsible heel.
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Glossed leather gives this square-toe shoe with 3-inch heel an elevated look.
Best mules
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The footwear brand taps podiatrists to develop shoes with built-in arch support, like these non-slip mules.
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This pointed-toe slide brings the drama thanks to its luxe velvet upper and quilted satin insole.
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An open-toe silhouette and wooden 1-inch kitten heel make these the perfect summer evening staple.
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These add a stylish sparkle to evening looks, with kitten spool heels that are easy to walk in.
Best booties
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The durable lug sole makes these suede and leather boots highly walkable, despite the 3.3-inch heel.
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The high point of this leather or suede ankle bootie: a sculptural 2.5-inch wedge heel.
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This special occasion stiletto bootie comes in neutral suede hues or an eye-catching gunmetal lame.
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The trendy cowgirl bootie gets an elegant upgrade with these two-toned canvas and leather stunners.
Best sandals
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These festive strappy sandals are made with sustainable leather and have a 3.3-inch wide heel.
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These ultra comfortable heels have a square toe platform and slim 3.5-inch block heels.
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Five millimeters of plush foam padding and a 2.5-inch heel make these sandals superior in walkable comfort.
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A lightly padded footbed adds cushion to these 3-inch ankle strap wedge sandals.
FAQs
What dress shoe style is the most comfortable?
Many types of dress shoes can actually be quite comfortable if you know which features to look for. A flat shoe is often the most walkable, as long as there’s plenty of wiggle room in the toe box. Lower heels are typically less taxing on your feet than higher heels, so be sure to check how many inches you’re committing to before purchasing. While a skinny heel like a stiletto doesn’t allow much real estate to balance on, a block or a wedge heel can be more stable. Steel rod stilettos offer more security and are more durable.
Look for brands that offer arch support, which can be found in flat shoes as well as some heels. If your foot is particularly wide or narrow, you can find shoes specifically designed to accommodate different foot widths.
How can I make dress shoes more comfortable?
With dress shoes, there can be a bit of a break-in period, so it’s not advised to wear a shoe for the first time ever for a long event with lots of standing or walking. If you have a new pair of dress shoes, especially leather ones, you should take a practice run in them for the first few times before the day of the event.
To get you through the break-in period, you can also rely on blister tape in any areas where the shoe is pressing on your foot or toes. With loafers and dress boots, you can find no-show socks to add a bit of cushion between your feet and the shoe. If you find the footbed too flat, try adding insoles.
