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Now more than ever, there’s a certain excitement that comes with dressing up for work or a special occasion. Following last year’s Covid-induced lockdowns, dressing up in something other than sweatpants has become an activity many women cherish. But even still, it’s often counteracted by the dread of squeezing into too-tight pumps or those beautiful but stiff leather loafers that might look cute but always leave behind blisters.
Truth of the matter is, dress shoes have earned a reputation for being uncomfortable. Beyond temporary soreness and abrasions, wearing ill-fitting or unsupportive shoes can negatively impact the health of your feet as well as that of your entire body. According to a report from the American Osteopathic Association (AOA), high heels place the foot at an angle and often throw the joints and muscles there out of alignment. This leads to poor posture, which in turn can result in pain in the lower back, neck and shoulders. What’s more, sporting styles with too-tight toe boxes can cause you to develop painful and unsightly bunions.
Sure, the most comfortable sneakers will always be your number one choice, but thanks to innovations over the last few years, dress shoes (even heels!) are now more wearable than ever. You just have to know what to look for.
What makes a dress shoe comfortable?
“Find a shoe with no more than a three-inch block heel and wide or flexible toe box,” says Dr. Najwa Javed, associate at Silicon Valley Podiatry Group and founder of E’Mar Italy. A solid block heel provides posture support and ample balance, while a wider toe area leaves room for feet to expand as they may swell throughout the day.
Finding a pair of dress shoes that suits your foot type is also important. “Try to choose a pair of shoes that match the shape of your foot,” says New York-based podiatrist and Vionic Innovation Lab member Dr. Jaqueline Sutera. “For example, if you have a square, wide foot or have bunions or hammertoes, avoid narrow, pointy toe boxes. Instead, opt for a rounder or square toe box.”
And for any women who experience the painful condition of plantar fasciitis, Dr. Sutera suggests shoes with cushion, arch support and a deep seated heel cup. “Patients with plantar fasciitis usually find relief and reduction in symptoms when wearing shoes with a heel drop (where the heel is higher than the front of the shoe),” she says. “For this reason, they should avoid very flat or platform styles.”
No matter your foot type, though, variety is key. “Don’t choose the same style in a few different colors, but instead have a few different options [to keep feet happy],” adds Dr. Sutera.
A range of on-trend, affordably priced labels like Everlane and Birdies as well as luxury brands like Sarah Flint and Gucci offer chic styles you can wear for hours without hobbling around in pain. From classic pumps to kitten heel and work-ready booties, they include craveable features like plush cushioning, chafe-reducing linings and expanded toe boxes.
Taking all this into account, we compiled the 20 most comfortable dress shoes for women that you’ll want to wear even while standing all day. Whether you have flat feet, wide feet, high arches or a foot condition like plantar fasciitis, our list includes specific options to suit every need. And since you’re here, check out our guide to the most comfortable dress shoes for men when shopping for any guy in your life, too.
Vionic Josie Kitten Heels
Vionic proves that comfort-driven footwear doesn’t have to look orthotic. This on-trend kitten heel style from the brand is done in a sleek tortoiseshell finish with a front seam on the toe box for leg-lengthening effects. Like the rest of the brand’s offerings, it’s designed with the help of podiatrists (including Dr. Sutera) and features a deep heel cup for stability, a proprietary molded footbed with arch support and added metatarsal padding.
Dr. Scholl’s Faxon Loafers
Dr. Scholl’s is here to provide you with one of the most comfortable loafers for women that won’t kill your feet on your daily commute. Offered in four standout colorways, the brand’s Faxon loafer is flexible and lightweight. The style includes a cushioned insole and quilted heel counter to reduce irritation on the back of the foot, plus a softly pointed silhouette that won’t crush toes. And if all that wasn’t enough to sell you on these, note that the style is also sustainably-made, featuring a fabric toe box, linings and topcloth crafted from recycled plastic bottles.
Lifestride Gigi Sling Pumps
Our list of the most comfortable dress shoes for women wouldn’t be complete without a style from Lifestride. The Gigi Sling pumps check off all the podiatrist-recommended boxes while remaining a timeless silhouette. They feature a three-part comfort system of breathable foam, extra arch and heel support for balance and stability and a flexible outsole that mimics the responsive feel of a sneaker. There’s so much innovation packed into these heels, your feet won’t know what hit them.
Hush Puppies Angel II Heels
Hush Puppies’ Angel kitten heels offer a heavenly feel for feet with a look that still adheres to most dress codes. Formed with a round toe to let your feet naturally splay, these shoes are set atop a cone stacked heel for a more balanced, stable fit. The pair is topped off with a soft lining, bouncy foam cushioning and a molded rubber outsole to keep you stable even when walking across slick hardwood or tile surfaces.
Birdies Starling Loafers
Not a fan of wearing heels? Birdies’ elegant flat loafers are a great alternative. Created with animal-friendly vegan uppers, these combine the cushiony comfort of a slipper with the elegant appeal of a smoking loafer. Dual-layer memory foam in the insole absorbs shock with each step and supports the arches, as soft quilted satin feels luxurious against the skin. A textured outsole completes the style for slip-free wear on many surfaces. As an added bonus, these come in a range of finishes — including velvet, faux leather, and woven or faux suede — to suit many wardrobes.
Naturalizer Tibby Sandals
During warmer seasons, your feet still should experience the same level of comfort without overheating. That’s where Naturalizer’s sandals come into play. The Tibby model offers breathable linings and underfoot cushioning with Contour+ technology, which is anatomically crafted to meet every contour and arch of your foot. Plus, wide straps, a sturdy kitten heel and non-slip outsole help to create a smooth and balanced design suitable for any occasion.
Clarks Eden Mid Monk Shoes
On days when temperatures start to drop, turn to Clarks’ Eden Mid Monk Shoes. They’re a special type of retro-inspired loafers that feature the brand’s signature Cushion Plus technology underfoot for comfort. These dress shoes will please almost everyone, but they are especially appropriate for women with flat feet. “In general, flat arches make feet more flexible, so women with fleet feet should opt for shoes that have more structure and support in the midfoot, along with the sole of shoe,” Dr. Sutera says. “Women with flat feet should avoid shoes that are super flexible, thin and soft.”
Everlane The Day Heels
There’s a reason Everlane’s Day Heel has earned a cult following. Available with either a smooth leather or suede upper, the design features a sturdy two-inch block heel for an appropriate lift with a ballet flat-inspired silhouette that sits comfortably on the foot. The elasticized heel stretches to fit every shape as a rounded toe follows the natural curves of the foot to reduce pinching at the toe, making these a great option for women with wider feet. “People with wide feet should avoid pairs with narrow, pointy or a stiff toe box,” Dr. Sutera says. “Look for wide, round, soft and mesh styles to help ensure there’s enough room for wider feet.”
Rothy’s Mary Jane Flats
If you’re in the market for a dress shoes that’s not only stylish and comfortable but also eco-friendly, this pair is for you. Made from recycled plastic water bottles, this Mary Jane-inspired flat from Rothy’s is soft, durable and machine washable. The pointed-toe silhouette and bow across the vamp offer dressier appeal. And even better, the bow accent is adjustable so you can customize the fit. This shoe comes in a range of solid colors and patterned finishes, from a classic black style to a golden yellow pair with gingham print accents.
Cole Haan 4.Zero Grand Loafers
These might look like loafers, but Cole Haan’s 4.Zero shoes sure make it feel as if you’re wearing sneakers. You’ll find dual-layered foam cushioning and a TPU sole with flex grooves that make for exceptional durability and all-day comfort. Combined with a timeless look, this style definitely earns a spot in any woman’s wardrobe.
Sarto by Franco Sarto Regal Pumps
These classic and sophisticated pumps come in a variety of colors to go with any outfit. They have a contoured block heel with a subtle tread for stability when walking, along with a cushioned footbed that leaves ample room for your foot to move and grow naturally. And the pointed toe is sleek while still being roomy enough so as not to pinch or cramp toes. In fact, the shoes’ near-perfect customer reviews prove how comfortable these really are.
Sabah Women’s Great Jones Shoes
The second you get your feet in a pair of Sabahs, you’ll understand why people love them so much. Each pair is handmade with exceptional attention to detail and craftsmanship with the softest Turkish leather. Once you break them in, these modern-casual dress shoes will feel custom-made to your foot.
Sarah Flint Perfect Emma Shoes
Beloved by stars like Amal Clooney and Meghan Markle, Sarah Flint’s designs are just as comfortable as they are chic. You’ll find an inset footbed, which means you get the support of a block heel without the typical weight, and thick padding in the arch area to relieve stress in the area with every step. They’re great for people with plantar fasciitis and can accommodate bunions, thanks to their expanded toe box.
Gucci Princetown Leather Slippers
Sure, everyone seems to have Gucci Princetown mules these days, but that’s because they’re straight up great shoes. The silhouette is an easy on-off style that can be dressed up for work and down for athleisure days, without ever compromising on comfort. The slight centimeter heel actually makes a difference in your stride, aiding in proper posture. Plus, we’d be remiss not to mention heavenliness of Gucci’s signature leather.
Marc Fisher Zala Block Heel Pumps
Marc Fisher’s Zala block heel pumps are a top-seller season after season. Not only is the style timeless, but women simply seem to love how comfortable they are (at Nordstorm alone, almost 500 people rated them with four stars or more). The streamlined silhouette adds elegance to any outfit, while the sturdy block heel will keep you steady for hours. Due to their slim toe box and lack of cushioning, though, keep in mind that these are best suited for women with narrow toes and neutral arches.
Söft Ameera Mules
If you’ve never owned a pair of Söft shoes, you’re missing out. This clog-style mule from the brand is cool and casual, while bringing height and sophistication to any look. It offers a smooth leather upper, chunky stacked heel and the brand’s signature arch supporting footbed for ultimate comfort.
Tod’s Kate Leather Pumps
There’s nothing quite like the soft Italian leather of a classic Tod’s shoe. The iconic brand is known for perfecting the driving loafer, including this block heel take on the classic style. Like fine wine, these loafers get better with age as the leather molds to your foot — making them a worthy investment your feet will love.
AGL Block Heel Pumps
AGL is another Italian footwear brand that prioritizes craftsmanship. When modern design meets lasting comfort, everybody wins. In this style, you’ll find a classic block heel just over two inches tall with a roomy yet supportive footbed for breathability and support. The rubber outsole makes for good traction while the sleek leather upper adds a soft touch.
Walking Cradles Belle Slingbacks
This classic slingback includes Walking Cradles’ trademarked Tiny Pillows insoles, which are formed with dual-density foam to provide more bounce with each step compared to memory foam alternatives. With its pointed-toe silhouette, the style adds a sophisticated touch to any outfit and a subtle two-inch lift. It’s available in a mix of widths ranging from narrow to extra wide, so even people with the widest feet can find a great fit.
E’mar Italy Aiden Heels
Any woman who’s worn a pair of E’mar heels will tell you how great they feel on their feet, all day long. The burgeoning brand was founded by Dr. Javed with a mission to create luxury heels that are actually super wearable. All E’mar shoes feature a multilayered foam padding with a patent-pending carbon fiber arch inlay for exceptional support. This chic, multi-textured pair from the brand also has an elongated toe box and recessed heel for better ankle stability.