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Most Comfortable Dress Shoes for Women
There’s a certain excitement that comes with dressing up for work or special occasions — but for many women, it’s often counteracted by the dread of squeezing into too-tight pumps or those beautiful but stiff leather loafers that 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 not only the health of your feet but also 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.
Nowadays, however, dress shoes are more wearable than ever — and not only when it comes to offerings from traditional comfort brands. A range of on-trend, affordably priced labels like Everlane and Birdies to designers like Sarah Flint offer chic styles you can actually wear for hours without hobbling around in pain. These looks offer perks like hidden cushioning, soft, chafe-reducing linings and expanded toe boxes.
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Doctor of osteopathy Sajid A. Surve explained to the AOA that the best heels and shoes should offer balanced height, ample toe space and a snug fit to minimize friction.
Whether you’re on the hunt for a classic pump, kitten heel or work-ready bootie, FN rounded up the most comfortable dress shoes for women that you’ll never want to take off. Read on to find the can’t-miss selection.
Everlane The Day Heel
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 2-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.
Naturalizer Tibby Sandal
During warmer seasons, your feet still should experience the same level of comfort without overheating — that’s where Naturalizer’s sandals come into play. These slip-on pairs offer hidden cushioning with Contour+ technology, which is anatomically crafted to meet every contour and arch of your foot. Plus, a sturdy kitten heel and widened straps help these sandals offer a smooth and balanced design for any occasion. The non-slip outsole adds grip to your step as well, formed with breathable lining to help reduce moisture buildup.
Clarks Laina Bootie
On days when the temperatures start to drop, turn to Clarks’ Laiana booties. Offered in solid colorways and textured shades for a pop of personality, these elegant boots have it all. The elastic goring creates stretch and mobility around the ankle as a leather sock lining aims to reduce chafing. The brand’s signature Cushion Plus cushioning then reduces strain on the ball of the foot and supports your natural range of motion for easy, all-day wear.
Birdies Starling Loafer
No a fan of wearing heels? Birdies’ elegant flat loafers are a great alternative. Created with animal-friendly vegan uppers, the brand combines 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 to suit many wardrobes, including velvet, faux leather, and woven or faux suede.
Sarah Flint Marigay Sling
Beloved by stars like Amal Clooney and Meghan Markle, Sarah Flint’s designs are just as comfortable and they are chic. This slingback heel from the brand features hidden elastic in the strap for a more secure fit and thick padding in the arch area of the footbed for elevated support. Rubber at the forefoot of the outsole adds traction on slicker surfaces, while a steel rod in the stiletto heel makes the pair more stable and durable — even at nearly 3.5 inches tall. The style comes in a floral jacquard finish if you’re looking for statement pair to add to you closet, as well as an all-black version that can complete many outfits. Peek-a-boo cutouts across the top add an eye-catching touch.
LifeStride Nadine Pump
Consider this your new staple pump. Equipped with a balanced 3.15-inch heel, this pointed toe silhouette offers a classic look with extra space built in for comfort. The expanded toe box and flexible uppers with curved side panels help take the pressure off the front and sides of your foot, while a cushioned footbed provides a soft base for every step. To top it all off, a traction outsole helps keep you stable during your morning commute or while working in-office.
Rothy’s Mary Jane
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 offers a dressier appeal as the the flat outsole puts your feet at ease. Plus, the bow across the vamp is adjustable so you can customize the fit. This silhouette comes in a range of solid colors and patterned finishes, from a classic black style to a golden yellow pair with gingham print accents.
Vionic Josie Kitten Heel
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, complete with a proprietary molded footbed, soft foam top layer and added metatarsal padding. Keep in mind that the brand advises only wearing the heels for a few hours at a time to start, so you can adjust to the feel of the pair’s elevated support.
Rockport Total Motion Pointy Pump
You can never go wrong with a classic pump like this pointed-toe pair from Rockport. Offering 3 inches of extra height, these heels come in over 20 different shades and fabrics to fit any outfit. They come equipped with TruTech padding for maximum shock absorption and responsiveness with each step, plus a cushy foam footbed. What’s more, hidden metal shanks in the midsole and outsole enhance the stability and sturdiness of the style. On top of all that, a suede split base helps reduce slippage and a foam backing ensures your feet are cushioned from all sides.
Ecco Block Heel Sandal
Ecco’s block heel sandals can easily be dressed up or down for any occasion. Plus, the comfort features ensure you’ll want to wear these 24/7. A thickened upper strap holds the foot in place, while a breathable smooth leather lining helps keep feet cool. A full anatomical footbed and last is designed with the unique shape of a woman’s foot to cradle its natural curves, cupping the arches and providing lift underfoot. The two-inch block heel also gives you a subtle boost of height.
Hush Puppies Angel II Heel
Hush Puppies’ Angel kitten heels live up to their name, offering 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 sturdy even when walking across slick hardwood or tile surfaces.
Dr. Scholl’s Faxon Loafer
Dr. Scholl’s is here to provide you with a work shoe 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. Additionally, its softly pointed silhouette boosts its dressier appeal without crushing toes. And as if all that wasn’t enough to convince you to purchase a pair of these, note that the style is also sustainably-made, featuring a fabric toe box, linings and topcloth crafted from recycled plastic bottles.
Anne Klein Evera Pump
Unlike most other traditional pumps, this pair from Anne Klein features a trendy square toe silhouette that’s quite of-the-moment. It’s designed with the brand’s iFlex technology, a lightweight foam cushioning with shock absorption and 90 degrees of flexibility to support the foot’s natural path of motion. It also boasts a sturdy 2.25-inch block heel, subtle hardware and a textured rubber sole for extra traction.
Aerosoles Long Beach Sandal
Add height and texture to all your ensembles with Aerosoles’ Long Beach sandal. Featuring a 3.5-inch heel, this snakeskin-embellished style is great for boosting shorter frames, yet doesn’t skimp on comfort. It features an advanced heel rest that balances your body weight towards the heel to take the pressure off the ball of your foot. It also includes a memory foam footbed and the brand’s Diamond Flex sole that absorbs and disperses friction from impact. The adjustable strap across the ankle helps to create a sturdy, custom fit.
Easy Street Chiffon Pumps
Opting for more comfortable heels doesn’t meet you have to give up your taste for glamour. Easy Street offers this glittering design with a classic pointed-toe silhouette and manageable kitten heel. The insole includes a generous amount of padding so you can step into any event confidently. The flexible uppers take the pressure off the sides of your feet, while an agile outsole bends for a more natural feeling flex. And best of all, the heels are offered in four different widths — narrow, medium, wide and extra wide — so you never have to feel constricted.
Chocolat Blu e Bai Sandal
Finished heel-to-toe in a smooth, rich leather, this chunky peep-toe shoe offers fun retro appeal that can easily transition from the office to happy hour. The cushioned footbed features thick foam for softness underfoot with a wider slingback strap that won’t dig into your heel. What’s more, the pair also features a smooth interior to prevent rubbing, as well as an adjustable closure on the slingback strap for a closer fit. Finally, a sturdy block heel ensures you can comfortably stand in these for hours.
Cole Haan Vannie Bootie
From a leader in comfortable footwear offerings, these Cole Haan booties offer a sleek way to bring support into your office attire. The shoe upper features a knitted, sock-like material that hugs the foot for a locked-in feel. Meanwhile, the heel and toe areas are covered with soft suede for a cool mixed media look. For days when you want to keep your outfit looking ultra-professional, wear the style peeking out of long trousers, as the suede finish offers a polished look that’s suitable for boardroom meetings and presentations. Finished off with a thickened 3-inch heel that’s designed to be easy to walk in, you’ll definitely want to add these to your cart in both the black and navy colorways.
Walking Cradles Belle Slingback
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 also adds a subtle 2-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.