'These Dress Shoes Are So Comfortable, I Could Wear Them All Night'

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Dress shoes can be so uncomfortable. Want a heel? You're in for a night of discomfort. Wearing leather? Make sure they're broken in before heading out. But finding a comfortable dress shoe shouldn't have to be such a chore. So, the editors and writers at Women's Health put a bunch of dress shoes that claim to be comfortable to the test to come up with a list of the 14 best options for every preference, from the best walking shoes to options for wide feet and even shoes for standing all day.

After weeks of testing, our favorite overall pick were the Sperry Seaport Heels because they have a high heel with arch support, so there's no pain in sight. Looking for a pair to wear to a wedding? Stewart Weitzman nailed their strappy heel with a thick platform that makes you feel like you're wearing nothing. IMO, the trendiest pair on this list is the Reformation Bethany Ballet Flat. Enough explaining—let's get into our suggestions for the best dress shoes that you don't dread wearing.

Seaport Heel

You may see a heel and immediately turn your head, but these Seaport Heels from Sperry deserve your attention. Per online reviews and a WH editor, they're actually super comfortable thanks to their 4mm EVA foam footbed. They also fit true-to-size, they're suitable for wider feet, and they're easy to pull on and off with the addition of a heel pull. These comfortable heels look so cute paired with anything from jeans to a casual dress, and they'll get you anywhere without causing dreaded foot pain.

Editor Review: "These boots have been my go-to work shoes this winter. The heel is pretty high, but it’s comfy enough to go from the subway to the NYC streets for hours on end. I love wearing them when I want to look put together. My only caveat is they crease pretty easily, especially in the front ankle area, but my jeans usually cover that part of the shoe anyways. On the flipside, the shoes are flexible enough that they don’t restrict movement or cause any weird chafing to my feet." —Jasmine Gomez, commerce editor at WH

Bethany Ballet Flat

I've been seeing these super chic ballet flats everywhere. While sometimes style doesn't equal comfort, these are different. The foot strap offers ankle stability while the slight heel protects your feet from getting too sore while you're out and about all day. They come in so many different colors and patterns—I'm personally loving the black mesh style, which offers a little peep toe action.

Editor review: Heels are out and flats are in! Not only are these flats super chic and modern, but they allow you to be comfortable, too." —Kristen Saladino, executive fashion director at WH

Saint Black

These may look like typical black loafers, but the chain detailing on the front of the shoe turn them up a notch for fancier events. Most importantly, the podiatrist-designed shoe has four layers of support and cushioning along with a utility-inspired sole and a super sleek upper. The shoe also features the brand's patented Sole Hero Footbeds, which cushion the heel and offer mega arch support to help with lower limb alignment. Each shoe you purchase also comes with a Sole Saver Pack, which are customizable insoles that cater to your exact feet.

Editor Review: "I love a chunky, sleek loafer, and this pair from Frankie4 are the most comfortable pair I own. I didn’t even need to break them in! They also come with a pack of different sized insoles for added comfort!" —Rose Lauture, assistant fashion editor at WH

Brooke Knee High Platform Boot

As someone who owns two pairs of Vagabond shoes, I'll be the first one to tell you that they're some of the most comfortable shoes I own. Although some pairs may take some breaking in because they're made with real leather, they feel like a dream once they've been worn a few times.

This specific pair of boots have a block heel and a platform to keep the foot protected. Plus, according to reviews, the calf area is stretchy enough to fit around many different sized calves, so you don't have to worry too much about them being too small.

Ada Fashion Square Toe Ankle Boots

Add these stylish and affordable chunky ankle boots from Amazon to-cart ASAP. Their budget-friendly price tag means you can wear them all over town without stressing over a little wear and tear. Trust, you'll find yourself wanting to rock these boots all day long.

Boasting a solid 4.5-star rating on Amazon, they've earned numerous positive reviews for their comfort, featuring a lower heel, breathable plush lining, and a slip-resistant outsole. A happy five-star reviewer sums it up: "I love these boots—they're incredibly comfortable, and I get lots of compliments when I wear them."

Women's Sofie Pump

These elegant pumps are made out of super soft and flexible suede and leather materials, so they're easy to wear and they feel flexible against your foot. Even though they have a slight heel, their patented Bounce footbed—it's made with layers of memory foam—makes you feel like you're walking in a comfy pair of sneakers.

Editor Review: "I love these shoes because they look so preppy and high-end, even though they’re less than $100. What I really enjoy about these shoes, though, is their soft, cozy footbed. It’s made with memory foam, which helps soften the blow of every step I take, and living in NYC I take a lot." —Jasmine Gomez, commerce editor at WH

Leather Pointed Ankle Boots

If you have wide feet and the quest for a pointed-toe shoe has been a struggle, look no further—this pair is legit tailor-made for you. Boasting a wide toe box and an elongated pointed toe, these shoes go the extra mile to ensure your toes have room to breathe, eliminating any discomfort from squeezing. As far as leather boots go, these gems require minimal breaking in; the moment you slip them on, it feels like you've owned them for years.

Editor Review: "I'm always pretty hesitant when it comes to buying a new pair of leather boots, especially when they have a pointed toe. As someone with wide feet, I typically struggle with a point, but these hug my foot in all the right places. Plus, they didn't require any breaking in—I immediately hit the town upon opening them and was out and about the entire night without complaints." —Lily Wohlner, associate e-commerce editor at WH

Square-Toe Water-Repellent Heeled Boots

If you haven't heard about Vivaia, they're kind of the epitome of comfort. First off, they're made with a super stretchy material that forms to your foot, no matter what shape or size it is. Their specially-designed block heel is also designed for all-day comfort if you're hitting the town. But what makes them the most wearable is their inserts, which are made from a cushioned feel microfiber that offers improved arch support and pressure relief. Plus, this specific pair is water repellent.

I have friends that own these shoes, and they all agree that they look adorable paired with anything and they're the most comfortable heels they've ever tried.

Satin Bow Ballerina Flats

Another pair of flats recommended by Saladino, this pricey but super elegant pair from Miu Miu takes the cake for the best splurge shoes on this list. Their leather outsole keeps the feet protected, and the round toe holds the foot in place during long days out and about. Online reviewers also rave about their comfort, saying they're enjoyable to wear all day long and they don't feel stiff.

Jadon Boot Smooth Leather Platforms

These shoes look casual, but they can easily be dressed up by pairing them with a dress or a skirt. They do take some breaking in, but once you wear them around a bit they are so comfortable and they'll literally last you forever (I've had mine for eight years and they're still going strong!). The key to their comfort? A wide, rounded footbed, a two-inch chunky platform, an inner ankle zip, and a heat-sealed upper and sole that provides extra padding and durability.

Editor Review: "I bought these boots four years ago now and they're still one of my favorite investments. They're extremely comfortable—I wear them literally everywhere—and I get compliments on them from everyone. Plus, they add a little height, which I love! I don't remember the break-in period being too long, either." —Addison Aloian, assistant editor at WH

Ivona

Wedding shoes can be super uncomfortable, but these platform heels from Stewart Weitzman go against all odds. They have a thick heel for stability, a large 4-inch platform to protect the ball of your foot, and adjustable ankle straps to hold the shoe in place as you ~strut your stuff~. They're suuuper affordable rn (under $300 for Weitzman is rare), so get your hands on them while you can.

The Day Glove

Many flats don't have arch support, but these keep your foot protected all day long thanks to a cushioned insole and a rubber outsole. They slide on the foot so easily, feature side vents for breathability, and hug your foot in all the right places so they're truly ready for anything.

Editor Review: "I am extremely fussy about shoe/foot comfort. I never wear socks, either. So I’m looking for soft, breathable shoes that look good everywhere and wear well because once I find the right fit, I just stay in them. These have no pinch points, regulate temperature well, and they are polished and modern. You’ll think you’re wearing sneaks and you’ll look classy and put together. Promise." —Laura McLaughlin, managing editor at WH

Black Leather Boots

IMO, everyone needs a pair of comfortable black boots to go out in, and I have been eyeing this particular pair for a while. They're chunky, they're funky, and they're perfect for everyday wear—just with a bit of an elevated twist. Comfort comes in with the patented and super cushioned OrthoLite recycled non-removable footbeds and EXTRALIGHT outsoles that provide lightness and shock control.

Plus, they're 30 percent off right now, so get your hands on them while they're affordable.

Cleo

Metallic is in, but uncomfortable heels are out. That's where these super comfortable Mary Janes come in. They're made with a proprietary plush insole with arch support, which was developed by biomechanics, so they're suuuper comfy. One online reviewer even said she walked an entire mile in these without an ounce of pain.

How we chose the most comfortable dress shoes for women

For months, Women’s Health editors, including associate commerce editor Lily Wohlner, have been researching the bestselling, most popular, and top-rated comfortable dress shoes. Lily reached out to the entire WH editorial team to see which pairs of dress shoes they actually wear in the their daily lives, from everyday options to special occasion faves. She examined their picks in comparison to the best customer reviews to narrow down a list of the absolute best comfortable dress shoes for women with a wide range of needs and preferences.

Shop more comfortable shoes

Most Comfortable Wedding Shoes | Most Comfortable Sneakers | Most Comfortable Heels | Comfortable Ankle Boots | Best Hoka Running Shoes | Best Walking Shoes

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