The 10 Best Comfortable Dress Shoes for Women of 2023

Jan 19, 2024

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Chic pumps, flats, and sandals that go from work to play with ease.

Not to state the obvious, but shoes are a crucial component to any look. What you wear on your feet can make or break an outfit—especially if it's for a dressier occasion. When shopping for women's dress shoes, it's important to keep versatility in mind. You want a style that's smart-looking, but also conservative (and comfortable) enough to wear in your day to day life.

The best place to start is with the classics: a pair of comfortable high heels, feminine ballet flats, or classy loafers. Then build out your collection with cute mules, elegant kitten heels, and platform shoes. Don't be afraid of incorporating some color and texture, too: While men's dress shoes commonly skew more neutral, women's shoes come in a variety of pretty shades that evoke both a mood and a season. At the end of the day, it all comes down to your personal style and taste.

Here, the best comfortable dress shoes that go from work to play with ease.

Sarah Flint's aptly-named pumps are as classic as it gets. With a slim stiletto pump and a perfectly-pointed toe, the high-heels will carry you from day to night, from boardroom meeting to happy hour, from garden party to black-tie gala, all without a second thought. Another plus: The shoes have a specially-designed anatomical arch and cushiony footbed that adds extra support and comfort with every step.

Size Range: U.S. 4—U.S. 13

Here's a dress shoe you'll be living in all summer long: Stuart Weitzman's editor-favorite sandals (Kate Middleton's a fan too!) come with a not-too-high, not-too-low stacked heel that's perfect for all kinds of occasions. And just to give you an idea of how supportive and comfortable they are: T&C's Emily Burack wore them in white for 12+ hours on her wedding day without a single ache or pain.

Size Range: 4—12

While wearing ballet flats with the signature bow detail at the toe is great for all kind of events, we'd argue wearing a pair with a touch of sparkle is even better for dressier fetes. These Manolo Blahniks are exactly what we had in mind and ideal when you want to give your feet a rest from heels, but still want to wear something that'll zhuzh up your look.

Size Range: IT35—IT42

A classic pair of loafers will always be a wardrobe essential, and these horsebit ones are timeless as can be. They can go with your favorite pair of jeans and white button down shirt or you can wear them with a blouse and maxi skirt for dressier occasions—you'll look chic either way. Oh, and the best part of all? They're available in over 10 colorways, so it might be smart to double up!

Size Range: 4—13

Metallics are always a "do" at dressier affairs. Combine that with platform sandals, and you have yourself a killer pair of shoes. Margaux's take on the style is the perfect sweet spot with a walkable 3-inch block heel and 1-inch platform, as well as the plush padding that feels like a dream to walk in, dance in, stand in—you name it.

Size Range: 2.5—14

Another great flat dress shoe: the mule. This velvet pair, with an elegant pointed toe and a crystalized Mary-Jane style strap, is the perfect complement to your LBDs, maxi skirts, jeans, and just about anything else in your closet.

Size Range: 5—12

Everything from the patent leather to the slight stacked heel and gold buckle detail on the strap makes these Mary-Jane pumps from Repetto hard to resist. You'll wear them for all your formal occasions, but you'll also definitely be sporting them to brunch, the office, and beyond.

Size Range: 36—42

Have an outdoor event to attend this summer? Loeffler Randall's beloved Penny sandal mules have you covered. According to T&C's Caroline Hallemann, "the thicker heel makes outdoor receptions more manageable as there's no sinking into the grass" and "the padded footbed ups the comfort factor." In other words, you get the best of both worlds in a summer dress shoe.

Size Range: 5—11.5

From the camel hue to the polished knotted detail and itty-bitty curved heels, these kitten sandals are the definition of a wear-with-anything shoe. Pair them with a maxi dress, pair them with a skirt, pair them with sleekest trousers you own—you really can't go wrong no matter how you style them.

Size Range: 34—43

A slingback is also a must-have dress shoe. This lacy pair was designed by a surgically-trained podiatrist and features a science-backed cushioning design to ensure all-day comfort.

Size Range: 35—42

Sophie Dweck is the associate shopping editor for Town & Country, where she covers beauty, fashion, home and décor, and more.

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