Stylish Men's Dress Shoes for Plantar Fasciitis and Diabetic Nerve Pain

Updated on November 13, 2019
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GreenMind has written extensively about style, especially shoes. This guide offers style options for men with foot pain.

Dress Shoes That Look Good and Relieve Foot Pain

Foot pain and discomfort can come from many sources, but two of the primary causes are nerve pain and plantar fasciitis. These are very different conditions with very different causes, but both can make walking and standing miserable. I have experienced foot pain through the years in my own fight with plantar fasciitis, and I'm always looking for stylish shoes that don't hurt my feet.

The shoes in this guide have been carefully chosen to give the benefits of foot comfort and style. It can be very difficult to find good-looking shoes that will give some relief to sore feet, and it's true that the more serious your condition is, the more likely it is that you'll need to sacrifice some style for comfort. The shoes in this guide are among the best options for a man suffering from nerve pain or plantar fasciitis who needs presentable dress shoes.

Cole Haan Watson Cap Toe Oxford II Shoes

As a teacher, I have to be on my feet all day. Things got really interesting for me when I developed the painful heel condition known as plantar fasciitis—a chronic irritation of the plantar fascia, which is a band of connective tissue that runs directly under your heel. The accumulated impacts of days spent walking, or running, brings the bony spur of your heel bone down onto the fascia tendon, and you wind up unable to walk without pain. There's very little you can do about it, other than wear shoes designed to ease the impact.

Unlike most of the other shoes in this guide, this Cole Haan pair doesn't look like an orthopedic shoe. I's true that a pair of true orthopedics, like those made by Dr. Comfort, will address the specific problem of foot pain and plantar fasciitis. Cole Haan shoes, on the other hand, are first and foremost dress shoes. But what you give up in orthopedics, you gain in style. When I began wearing these Cole Haan cap toe Oxfords, my heel pain improved, and I didn't have to sacrifice looking sharp.


  • Leather upper
  • Imported
  • Cushioned footbed for heel-strike protection
  • Rubber sole
  • Grand.OS comfort technology
  • Sharp classic cap-toe styling

What Is Plantar Fasciitis?

It started for me with a nagging, aching pain in my heels. I had decided to run my first-ever half-triathlon at the age of 49, which was a noble gesture but involved some realities of the aging process. I was actually fine throughout the training process, and even the race was fine, since I was just trying to finish and I didn't puch myself too hard.

But after the race, I rested for about a week, and then went for a run. I pushed myself, and even took on some hills, which I usually avoided. That was all it took, and a couple of days later I found that every step I took produced a dull but intense ache right at the bottom of my heel.

I finally went to a doctor, and she told me all about the joys of plantar fasciitis. It starts when the band of ligaments that run under your heel, your "plantar fascia," gets insulted by being banged against the bones of your heel. This typically starts when you begin a new running regime, or start walking/running up hills. The irony is that you're trying to get in shape, running and jogging, and because of that you get a painful condition that keeps you from running! Every step smashes the band of connective tissue against the knobby bone of your bottom heel, and over time it can damage the tendon. When this happens, your plantar fascia becomes inflamed and painful; as a result, every step hurts.

There is no cure for plantar fasciitis. All you can do is try to rest your heels, but that means not walking, which is not an option for most of us. So since we have to walk, we need shoes that cushion the heel strike as much as possible. This guide offers some good choices, some of which are some specifically designed for rehabilitation of foot pain, including nerve pain, and some of which are more designed for style, and are easy on your feet as an added bonus.

Learn About Plantar Fasciitis from the Mayo Clinic

Orthofeet Gramercy Diabetic Plantar Fasciitis Dress Shoes

Of the shoes in this guide, I would say that this is the pair that looks the most like an actual orthopedic shoe. I include it partly for comparison, since it's easy to see the difference between this and the sleek pair of Dr. Comfort therapeutic wing-tips at the end of the article. But these shoes are also the best-equipped to deal with the often debilitating issues of peripheral neuropathy that can be one of the most challenging symptoms of diabetes. The orthotic features of this pair are truly impressive.


  • Premium orthotic insole
  • Anatomical arch support
  • Cushioning heel pad conforms to the contours of the foot
  • "Easy Gait "Ortho-Cushion™ System
  • Air cushioning softens step
  • Biomechanically engineered to alleviate stress on the joints
  • Soft, non-binding upper
  • Extra depth design and wide toe box eliminates pressure on bunions
  • Soft, seam-free interior lining
  • Foam padding

Clearly, the orthotic features of this shoe set it apart from other pairs in this guide -- but at the expense of sharp style. The features of the more stylish shoes listed here are worth comparing to this shoe to find your perfect mix of therapeutic features and style.

Surgery for Plantar Fasciitis

My plantar fasciitis never got quite this bad, although I did do some research about my surgery options when the pain was at its worst. While surgery is of course a drastic decision, when you're suffering from a condition that never seems to get better, and is aggravated literally every time you take a step, going under the knife starts to seem like a reasonable idea. In general, the people with plantar fasciitis who do decide on surgery are athletes who need to recover and can't stay off their feet for two or three months.

Dr. Comfort Classic Extra Depth Dress Shoe

This is a sharp pair of shoes. It's one of Dr. Comfort's "Men's Dress Collection" line, which I like because I truly hate walking out into the world looking like I'm wearing orthopedic shoes, even though I might be. Somehow Dr. Comfort finds a way to put therapeutic features into sleek, classic dress shoes. This pair of therapeutic cap-toes is good looking, but I prefer my Cole Haan cap toes (above), because I love Cole Haan and they're just about as comfortable as therpeutics, at leat as fat as my plantar fasciitis is concerned.

For wing-tips, though, I favor the Dr. Comfort pair at the bottom of this guide.


  • Leather
  • Dr. Comfort Gel Insert Included.
  • Classic design
  • Lightweight outsoles
  • Smooth leather interiors.
  • Lightweight
  • Seamless and padded lining.
  • Sizes: 6-15 - Widths: B/D, E/2E, 3E/4E
  • Hand burnished leather

This shoe gets excellent ratings from users, with comments mentioning the classic style that works for any occasion and their effectiveness for the pain of plantar fasciitis. One user did mention that for extra wide orders, the shoes run a half-size bigger. In general these are some of the best-reviewed orthos available.

Another Cause of Heel Pain: Weight Gain

The increased impact caused by running, especially by running up and down hills if you're not used to it, is one of the most common ways to get plantar fasciitis. But there's another cause, one tat is becoming more and more prevalent in the US thanks to the country's obesity epidemic—weight gain. As bad luck would have it, weight gain and other lifestyle issues can contribute to diabetes as well. Put it all together, and weight gain becomes one of the most serious root causes of foot pain.

If you have foot pain, especially heel problems where the heel bone impacts the fascia tendon, then you should consider trying to lose a few pounds—in addition to being generally good for you, the lower weight means lesser impact, and less impact means less pain in your heels.

Apex Men's Dress Shoe Black

I myself am not a fan of black dress shoes, and so I don't wear them often enough to call for a pair of orthopedic shoes. But I do like the clean style of these Apex therapeutic dress shoes. They have solid materials and an excellent reputation among their customers.


  • Full-grain leather upper
  • Removable EVA insole
  • Firm heel counter
  • Soft padded collar
  • Soft leather linings for comfort and breathability
  • Polyurethane outsole for cushioning, traction and stability

The manufacturer notes that the Lexington collection features an advanced EVA performance insole for maximum comfort. This therpeutic shoe, like more or less al therapeutic shoes, is often a source of relief for those of us suffering from foot pain, including bunions, arthritis, or who need need extra shock absorption as they recover from plantar fasciitis.

Diabetic Foot and Nerve Pain

Diabetic Neuropathy, which essentially means diabetic nerve pain, is a more serious condition that plantar fasciitis because it affect systems throughout your body. The imbalance in blood sugar that is the primary problem in diabetic conditions can cause all kinds of problems, but one of them is nerve pain that tends to affect the legs and feet the most. For some people, the pain is relatively mild, but for others the damage to the nerves can be very serious.

There are essentially four kinds of diabetic neuropathy, but the most common form is known as peripheral neuropathy. This complication of diabetes first affects the feet and legs, but can spread to hands and arms. Symptoms are often worse at night. According to the Mayo Clinic website, other symptoms of peripheral neuropathy can include:

  • Numbness or reduced ability to feel pain or temperature changes
  • A tingling or burning sensation
  • Sharp pains or cramps
  • Increased sensitivity to touch—for some people, even the weight of a bed sheet can be agonizing
  • Muscle weakness
  • Loss of reflexes, especially in the ankle
  • Loss of balance and coordination
  • Serious foot problems, such as ulcers, infections, deformities, and bone and joint pain

There's no question that this is a serious, even life-threatening condition. If you think you may have diabetes or any of the above symptoms, see you doctor right away! The sooner you catch diabetes, the sooner you can begin treating it and the better you can control the damage.

Dr. Comfort Wing-tip Therapeutic Extra Depth Dress Shoe

I chose these shoes for plantar fasciitis heel pain chiefly because I can wear them with a good-looking suit and it won't look like I'm wearing orthopedic shoes. These are some good-looking wing-tips by any standard, and once again Dr. Comfort finds a way to make orthopedics look stylish. People experiencing nerve pain may also get some relief from these handsome shoes. Honestly, I wish they would change the name of the company. "Dr. Comfort" sounds to me like an easy-listening cover band playing at a Ramada Inn lounge. These shoes deserve better! But no matter. If you're looking for a healing shoe that works with almost any dress look, then these sharp therapeutic wing-tips are a great choice.


  • Leather uppers
  • Classic wing-tip style
  • Dr. Comfort Gel Insert Included
  • Part of Dr. Comfort's Mens Dress Collection
  • Lightweight outsoles
  • Smooth leather interior
  • Seamless, padded lining.
  • Sizes: 6-15 - Widths: B/D, E/2E, 3E/4E

Customers, including people with diabetic nerve pain, give this pair of orthopedic dress wing-tips high marks. They're wide enough to cushion bunions, and several users specifically mention the shoe's effectiveness for dealing with the pain of plantar fasciitis. They also mention to excellent support and the classic look.

Look Good, Pain Free


The following sources were consulted for this guide:


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