Found: Podiatrist-Approved Dress Shoes for Heel Pain

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Plantar fasciitis is a painful foot condition when inflammation develops in a band of tissue, known as the plantar fascia, that runs along the bottom of your foot. It typically develops when excessive stress is placed on this ligament that absorbs our body weight with every step. This can come from prolonged movement, not providing your feet with sufficiently supportive shoes, or a combination of both. Long distance runners and other endurance athletes are commonly affected, as well as people with jobs that keep them on their feet for most of the day.

However, you can also get plantar fasciitis from wearing shoes with little or no arch support and cushioning. Men’s dress shoes are common culprits, thanks to stiff materials, hard outsoles, and large heels. Fortunately, choosing one the best dress shoes for plantar fasciitis can alleviate and even eliminate your foot pain.

Our style editors know a lot about shoes but we’re no doctors, so we called in an expert for advice. “My main thing to look for in dress shoes is proper arch support,” says New York City-based podiatrist Dr. Brad Scheffer, D.P.M. “Dress shoes can have little to no arch support and are very hard and rigid, depending on which brand you buy.”

So choosing a lighter, more comfortable dress shoe sole is half the battle. That will provide the give and support that your feet need to minimize discomfort. If you prefer a traditional heel, then stick to rubber outsoles over leather and keep heel height to a minimum. Dr. Schaeffer pointed out that you don’t need to drop a lot of money to get comfortable dress shoes. “I have seen very expensive shoes with no support and vice versa,” he explained. “It can be very hit or miss.”

You can pick up a pair of the best dress shoes for plantar fasciitis with any budget, as long as you look for the three key features: a flexible outsole, supportive insole, and strong arch support. Along with picking the right shoes, Dr. Scheffer insists that stretching is key to relieving foot pain. So check out the best dress shoes for plantar fasciitis below, and make sure to stretch out your feet before and after you put them on.

ØriginalGrand Wingtip Oxfords

When we asked Dr. Schaeffer which shoe brands he recommends for dealing with plantar fasciitis, he had a clear favorite. "Cole Haan is my go to," he explained. "Because they have a lot of room and cushion without sacrificing support!" The American footwear company has been a leader in making men's dress shoes more comfortable.

By using lightweight outsole technology borrowed from athletic shoes, Cole Haan provides exceptional support and flexibility for your feet. The ØriginalGrand line also provides ample arch support from the insole, as well as soft leather uppers. Best of all, you still get a classic dress shoe look with the Wingtip Oxfords.

This comfy dress shoe currently comes in ten different color variations, but our top choice has to be the Dark Chocolate-Black. Deep and rich brown pebble grain leather looks good with jeans, chinos, and even tweed pants. These kicks will complete any fall or winter outfit, be it at the office or off duty.

Slipper

Making a more comfortable, easy-to-wear moccasin was the that mission Easymoc started out with. Every shoe is hand made in Maine with the premium materials. Horween Chromexcel leather from Chicago is used for the upper, which is some of the finest in the world. Vibram rubber, which is the industry standard for boots, is used for the outsole.

These mocs feel as good as they look thanks to Ortholite insoles, which provide exceptional cushioning and support. The outsole is tough but flexible enough to move like a sneaker. Better still, it can be resoled when it starts to wear out.

Our style editors love Easymocs as the ultimate leisure shoe. The exceptional quality leather and moc toe give the impression of a high end boat shoe or even a loafer. Yet, the comfort level is like wearing your favorite house slipper.

Whiddon Mid

As a dressier take on the desert boot that Clarks is known for, the Whiddon Mid is among the most comfortable dress boots you'll ever find. The leather upper is soft and flexible a low and wide opening to maximize ankle mobility. An OrthoLite footbed lining provides exceptional cushioning and arch support. The heel is minimal for a boot, so your foot will lay naturally.

Clarks is another brand that comes highly recommended by Dr. Schaeffer. Most boots and shoes offered by the British brand have soft and flexible outsoles. They usually come with some sort of supportive insole built in as well.

Heavy boots can be tough on planter fasciitis, so we like this chukka boot as an alternative that still has a plain toe boot look. The low and open ankle moves like a sneaker, but you can style this the same way as you would any other boot. Rock them with a pair of dress pants and a collared shirt for a smooth office look.

Marando Wing Tip Derby

Don't be fooled by appearances, because this may look like an old fashioned leather wing tip, but it is actually optimized for comfort. Florsheim designed a fully rubber outsole to look like a classic leather version while providing far better traction and give. The inside is a plush Suedetec lining that is both comfortable and breathable.

A cushioned footbed is removable, which is another feature Dr. Schaeffer says to look for. Arch support can always be upgraded in a dress shoe by adding an insert. Especially one that is customized for the shape of your foot.

Our style editors love a good wing tip derby. It looks great with a suit as an upgrade to standard plain toe dress shoes. However, it also plays well with chinos and jeans for a casual look with an oxford shirt or crew neck sweater.

Citytray Cap Toe Tie

Ecco has a reputation for making some the most comfortable dress shoes on the planet. That's why the brand always on any short list of podiatrist-recommended shoes for dealing with foot pain. Not only is the Citytray line one of the most comfortable options, the Cap Toe is a perfectly sleek office shoe.

The leather derby style upper is an essential men's dress shoe feature, while the cap toe provides just enough detail to keep things interesting. The rubber outsole is soft, grippy, and well balanced. Where this shoe really shines is with the Ecco Fluidform insole that provides optimal motion and support throughout your foot.

We're fans of the Citytray Cap Toe because of how simple it is to style. With anything from chinos and a cashmere sweater, up to a full suit and tie, you can't go wrong with these shoes. The running shoe level comfort is just icing on the cake.

Tesoro Penny Loafer

This swanky penny loafer from To Boot New York is actually handmade in Italy. The upper and outsole are fine Italian leather, made entirely by hand. What sets these slip-on shoes apart is the built in cushion and arch support, which you usually don't find in a shoe like this. Even though the outsole is leather, it is still remarkably flexible.

In general, experts would steer you away from all leather loafers since they can be uncomfortable, but these ones are an exception. You can get that laidback loafer style that is so in right now, while still providing your arches and heels with the support that they need. No one will be any the wiser.

Loafers are a favorite of our style editors, especially when they have that luxury finish like these ones. There really isn't any look that you can't wear loafers with these days, so you want them to be as comfortable as possible. These are hands-down some of the most comfy options we've come across.

The Original

Amberjack stands out among men's dress shoes with its innovative outsole design. Built from TPU composite, the front of the sole is light and flexible while the back is harder for more support. The whole thing is smooth and angled like a running shoe. Meanwhile, the upper is full grain leather with a soft sheep skin lining. Essentially, you get the best of both worlds with athletic design on the bottom and dress shoe design on the top.

Another unique feature of Amberjack is the fact that the brand only has one dress shoe design, but it comes in over a dozen different colors. That is some serious confidence, but The Original has the function and style to back it up.

If you're on your feet all day long for work, we highly recommend this dress shoe. The simple plain toe appearance works with any business attire and the insole and outsole design will keep your feet happy.

Plain Toe Derby

When it comes to high end dress shoes, Dr. Schaeffer is a fan of Tod's because of the built in support. This chunky derby is one of the most fashionable looks for men's shoes these days. While there is a large lug sole, it is rubber for ample flexibility. The drop between the heel and toe is not very large either, so your arches will not get strained.

Bulky leather dress shoes can be a source of foot pain, especially if you have planter fasciitis, but Tod's are built well enough to avoid those issues. Every pair is hand made in Italy with soft leather and a supportive insole. The only issue may come from how heavy the rugged rubber outsole is.

We love these derby shoes styled with jeans and a blazer, which is an essential look right now. You can wear them to dress up but they actually work better as a casual dress shoe. Think of them as a fancier alternative to your go-to sneakers for a night out.

Strandmok Cap-toe Oxford with Dainite Rubber Sole

Suede is softer than leather so it naturally has more flexibility, making it an excellent alternative if you're dealing with plantar fasciitis. Allen Edmonds makes a beautiful suede cap toe brogue with a rubber outsole for even more flexibility. The CustomCork insole is designed to mold to your feet, providing optimal arch support.

Every Allen Edmonds shoe is made in Wisconsin using old fashioned techniques. The result is footwear that will stand the test of time. The 360 Goodyear welt on these oxfords means that you can get them resoled, which is relatively affordable with a rubber sole.

A light blue suede dress shoe is great as your second or third pair of dress shoes. It may not be ideal for the office or your next groomsman assignment, but it is more fun than standard leather and makes a classier alternative to sneakers. Our style editors have rocked these shoes with chinos and a cardigan, as well as jeans and a blazer with a t-shirt.

What to Look for in Dress Shoes for Plantar Fasciitis

Arch support, a padded insole, and flexible outsole are the key features that you want to look for when dealing with plantar fasciitis. Caring for your arches should be your top priority, according to Dr. Schaeffer. Most dress shoes do not have built in arch support so always check the details if you are shopping online or inspect the inside of the shoe if you are shopping IRL. Of course, trying a shoe on is the only way to truly know if your feet arches are getting the support that they need.

Look for softer outsole materials like rubber and composites. Most dress shoe companies borrow outsole designs from athletic shoes these days, which deliver far more support and mobility. More flex from the outsole means less stress on your plantar fascia and the rest of your feet. Minimizing the heel drop—which is the difference in height between the heel and the rest of the sole—is also helpful. This is a common source of plantar fasciitis pain for women, but men’s dress shoes have heels too so it is an often overlooked cause. Overall, you want to keep your feet as flat as possible, your heels cradled, your arches supported, and your outsoles flexible.

The best hack for any dress shoe, according to Dr. Schaeffer, is to swap out the insole for an orthopedic inset with better arch support. Which means that you should look for shoes with removable insoles. Most shoe companies will indicate this feature in the description but you can always contact the brand directly through email or social media if it isn't provided.

Meet the Expert

• Dr. Brad Scheffer, D.P.M., is a board-certified foot surgeon with Central Park Sole in New York City

How We Selected

Brad Lanphear is a style pro with more than a decade of experience testing and styling men's shoes, including dress shoes for plantar fasciitis. For this story, he and Deputy Commerce Editor Christian Gollayan tested over 50 dress shoes and evaluated their arch support, insole comfort, and just how great they looked. They also interview Dr. Scheffer for his product recommendations, and combed through hundreds of five-star reviews from e-commerce sites they trust, and also scanned through countless Reddit threads like r/malefashionadvice, for unbiased opinions on the best Harrington jackets to shop.

Shop More of Our Favorite Comfortable Shoes

Shoes for Standing All Day in | Arch Support Shoes | Business Casual Shoes | Insoles for Plantar Fasciitis | Running Shoes for Plantar Fasciitis | Flip-Flops With Arch Support | Work Shoes | Walking Shoes

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