Whether it’s because you’re a keen runner in your free time or your job requires you to stand all day, Plantar Fasciitis can be particularly frustrating when wearing dress shoes. The stabbing foot and heel pain can be overwhelming and leave you completely incapacitated by the evening.

Fortunately, we’ve developed this guide with you in mind. Read on to discover the Best Men’s Dress Shoes For Plantar Fasciitis:

  1. Athletic Dress Shoe: Amberjack The Original
  2. Oxford Shoe: Wolf & Shepherd Longwing
  3. Monk Strap: Propét Graham
  4. Brogue Shoe: Rockport Almartin
  5. Derby Shoe: SAS Ambassador
  6. Chukka Boot: Vionic Chase

Found the right ones for you? Use the links above to jump ahead or scroll down to keep reading.

We’ll also take a brief look at the features dress shoes can offer to generally improve your condition.

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What Are The Best Dress Shoes For Plantar Fasciitis?

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1. Amberjack The Original [Athletic Dress Shoes]

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Counting on an experienced team of founders boasting experience with industry giants including Allen Edmonds, Cole Haan, and Coach, Amberjack released their first pair of shoes, The Original, in 2020. Since then, they’ve won over endless customers with an ever-expanding shoe catalog that puts comfort and classic design cues at the forefront of every design.

Amberjack pairs high-quality leather uppers, in both full-grain and Italian suede varieties, along with their proprietary dual-density outsole. Internally, their shoes employ Amberjack’s trademark memory foam insole that molds to your specific foot shape after just a couple of wears.

The result is a custom-fit dress shoe that looks dashing on the outside and wears beautifully on the inside.

How To Wear

Amberjack’s growing catalog now includes three different styles of shoes: Derby/Bluchers, Venetian-style Loafers (pictured above), and Chelsea boots. Depending on your needs and the requirements of your workplace, any or all of these may be appropriate for you.

If you’re not looking for a pair of dress shoes for the office but rather a formal pair of shoes for a night out on the town, then all of Amberjack’s styles are likely to fit your needs.

Best Colors

Each of Amberjack’s shoes is available in several colors and leather types; nevertheless, all possess the same construction, ensuring they all wear as comfortably as the others. If you’re going for formal, the full-grain leather styles are the best option. However, if you’re a fan of suede, consider their Grizzly suede upper, which is a lush brown tone sure to age beautifully the longer you wear them.

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2. Wolf & Shepherd Crossover Longwing [Hybrid Oxford Shoes]

Wolf & Shepherd Best Dress Shoe For Plantar Fasciitis
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Inspired by athletic shoes, Wolf & Shepherd has devised some of the most premium and comfortable dress shoes that we’ve yet to see. Expect features such as full-grain Italian leather uppers, ultra-soft linings, cushiony memory foam insoles for excellent arch support, and athletic, high-density TPU outsoles.

The comfort provided by Wolf & Shepherd’s shoes definitely makes them one of our favorite pair of dress shoes for plantar fasciitis. If these longwings aren’t quite your style, W&S also offers wingtip and loafer options that will allow you to wear dress shoes without sacrificing relief from foot pain.

You may notice that W&S doesn’t outright advertise their styles as dress shoes for Plantar Fasciitis. However, the characteristics that make their shoes comfortable for regular wear also help them provide ideal foot pain relief.

How To Wear

With a contemporary look that nonetheless remains elegant, these are the ideal shoes for just about any occasion, including the office. They’ll look great in all business casual settings, just as much as if you were to wear them out to dinner.

Best Colors

Whilst you could also opt for a honey tan or maple brown leather Oxford, we find that the classic black is much more practical. If these are your first Oxfords, we’d recommend black above the others, as you’ll be able to use them for more formal events.

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3. Propét Graham [Orthotic Monk Straps]

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A discreet yet stylish pair of orthotic dress shoes, these well-designed monk strap shoes leave your entourage none-the-wiser. However, you can still benefit from deep heel cups, a removable footbed, and an open-cell PU foam insole for relief from foot and heel pain.

If you’re one who struggles to find just the right fit, it’s also worth noting that the Propét Grahams can be purchased in both medium and wide widths.

How To Wear

A versatile dress shoe style with a rounded toe box, you can pair these with business casual attire as well as more formal outfits. For instance, they’ll look great with jeans but you could even slip them on whilst wearing a classic suit.

Best Colors

We’d recommend the black full-grain leather if you have more formal needs. However, the brown is a versatile choice that would fare well if you tend to dress up or down depending on the day.

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4. Rockport Almartin [Orthotic Brogue Shoes]

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Rockport is a reputable brand that also offers orthopedic dress shoes that aren’t too conspicuous or clinical. With the Almartins, you can enjoy the look of traditional men’s dress shoes and not forgo the comfort you expect from your go-to walking shoes.

Both subtle and stylish thanks to the decorated leather upper, you’ll be able to enjoy the comfort of the EVA footbed and rubber soles which provide the wearer both stability and comfort.

How To Wear

Great for both business professional and cocktail attire wear, these are classic brogues that feature all the perfing and pinking that you’d expect. They’ll even add a little stylish flair, which is quite surprising for orthotic shoes!

Best Colors

Unfortunately, these brogues are only available in black, which is a shame. After all, brown is a more traditional color for brogues. Nevertheless, even in black, these brogues look very stylish indeed!

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5. SAS Ambassador [Orthotic Derby Shoe]

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Another subtle shoe that’s designed with built-in orthotics for more severe disorders, these are worth trying if you have a bad case of Plantar Fasciitis.

With the Ambassadors, you’ll benefit not only from great arch support but also from a wide toe box as well as the proprietary SAS Tripad Cushion removable insoles that addresses the three main pressure points of the foot.

While the SAS Ambassadors are more expensive, the aforementioned pain relief technology it employs, along with the durable rubber outsole, will ensure that you get your money’s worth in foot pain relief that lasts for years and not just months.

How To Wear

Derby shoes are a relatively versatile style of footwear that can be worn with casual outfits but more formally, too. However, they can’t be worn too formally as the open-throat lacing system style is considered too bulky for evening wear.

Best Colors

If you’re just looking for comfortable dress shoes for work, we’d recommend the black leather. However, if you want a more versatile shoe for business casual wear as well, the brown is a solid choice.

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6. Vionic Chase [Orthotic Chukka Boot]

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Another classic but less formal style of shoe is the Chukka. Whilst they’re not strictly a dress style, these Vionic shoes are formidable for people suffering from Plantar Fasciitis.

The Chase Chukkas feature a removable EVA footbed that was specially designed by podiatrists to help with plantar fasciitis. Accordingly, they provide arch support and heel support that aims to realign your feet to their natural position.

How To Wear

Especially appropriate for slightly more casual wear, they’re great all-year boots with a very stylish finish. In fact, they’re indistinguishable from regular chukka boots. These look great in business casual attire but fit right in with jeans and a T-shirt.

Best Colors

There are both tan, brown, and black options, which are each made from a water and stain-resistant upper. We find that the black is a touch too formal whilst the tan is a very versatile color choice for dressing up and down.

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What Is Plantar Fasciitis?

Although you may have already read about it in our specific Plantar Fasciitis shoe guide, Plantar Fasciitis is a well-known disorder that is believed to affect nearly a third of all American adults between the ages of 40 and 60.

Whilst sports enthusiasts are often the most prone to plantar fasciitis pain due to intense exercise, it can also affect pregnant women and people with obesity issues. Furthermore, standing all day can be a contributing factor, which many people have to do for work.

According to the American Podiatric Medical Association, the condition is brought along by prolonged or repetitive strain applied to the Plantar Fascia. This is a thick band of connective tissue on the underside of the foot, running from the heel bone to the underside of the toe box, that offers natural shock absorption when standing, running, or walking.

What Is Plantar Fasciitis

It was originally presumed that Plantar Fasciitis was inflammation of the band on the underside of the foot until it became apparent that this was merely a symptom. In fact, the repeated pressure and strain applied to the Plantar causes micro-trauma and fissures along the length of the tissue.

The result is chronic stabbing arch pain that can put Plantar Fasciitis sufferers out of action for months. However, outside of other therapies and treatments, there are orthotic dress shoes that can help alleviate the condition.

How Do Men’s Dress Shoes Exacerbate Plantar Fasciitis?

There are a number of reasons why dress shoes are often a culprit causing Plantar Fasciitis. One of the most common reasons for this is that, on many occasions, men tend to purchase dress shoes based solely on looks. The shoes may fit poorly, but we’ll try disregarding the discomfort since they are aesthetically pleasing.

You’ve likely found yourself justifying the initial discomfort of a pair of beautiful dress shoes with phrases such as “They’ll get more comfortable the longer I wear them” or “my feet just have to get accustomed to these.” Indeed, most dress shoes have some sort of break-in period, but significant discomfort from the get-go is always a bad sign, no matter how attractive the shoes are on the outside.

Along these same lines, proper fit is critical when it comes to alleviating plantar fasciitis or at least preventing shoes from exacerbating your foot pain. Moreover, dress shoes tend to cause foot and heel pain because they often lack arch support, lack shock resistance, are heavy and are not nearly as malleable as athletic shoes.

Men’s dress shoe manufacturers should be proactive and take these considerations into account when designing their shoes. If they don’t, the end product is often an uncomfortable one. Yet, there are many dress shoes on the market that do not, in fact, attempt to mitigate these vital concerns.

Finding The Best Dress Shoes For Plantar Fasciitis

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Firstly, bear in mind that the best dress shoes for Plantar Fasciitis work as a preventative measure rather than a cure. You could purchase the most expensive men’s dress shoes and these may not provide any relief from foot pain if you’re not also engaging in some sort of treatment such as physical therapy.

If you are prone to the condition, undertake activities that may cause it, feel pain in your feet on occasion, or generally consider yourself as someone with sensitive feet, it’s best to invest in supportive shoes to provide the necessary protection.

However, orthotic dress shoes for Plantar Fasciitis can indeed contribute to your therapy. They work by taking pressure off the Plantar itself by providing cushion and additional arch support elsewhere. In the end, the shoes function as a secondary Plantar so the tissue’s tears can begin to heal.

Best Dress Shoes For Plantar Fasciitis: Features To Look For

If you’re checking out the market in search of the top men’s dress shoes for Plantar Fasciitis, here are a few features to keep in mind:

  • Lightweight Materials: Probably one of the most efficient ways to take pressure off the Plantar Fascia is by lessening their load. Ultra-lightweight dress shoes are becoming a more popular option and will grant you the most fundamental relief.
  • Arch Support: Supporting the arches will also reduce the strain taken by the arches. However, be sure to opt for excellent arch support that corresponds to your feet’s contours. Too much or too little can worsen the pain.
  • Cushioning: A characteristic that used to be overlooked in a dress shoe, you’ll start to see it more and more. However, opting for dress shoes with superior cushioning will provide extra comfort and foot support.
  • Improved Stability: Brought by wider heel counters and deep heel cups, this prevents your feet from pronating and ensures that the Plantar Fascia doesn’t have to compensate for an incorrect stride. Individuals with flat feet are particularly susceptible to such foot instability, leading to chronic foot pain.
  • Ethylene Vinyl Acetate: EVA is a popular shock-absorbing material that is usually found in either the midsole, insole, or even the heel. Broadly speaking, the best dressy plantar fasciitis shoes will absorb shock as best as possible (so that your foot doesn’t have to.)
  • Removable Orthotic Footbed: Often made from EVA or leather-lined, removable insoles are ideal. This way, they can be replaced with more customized ones that fit the contours of your feet, which will provide additional arch support.
  • Polyurethane: Like EVA, PU is another common shock-absorbing material used for making comfortable dress shoes. More hard-wearing, it tends to be used as an alternative to rubber outsoles. However, sometimes it can be used in a foam form for either the insole or the heel.
  • Rubber Outsoles: Whilst this depends on the quality of the rubber, more natural variants will provide a very cozy bounce. Individuals with foot issues will find both the traction and comfort better than the more traditional leather outsoles and stacked heels found in premium dress shoes.

Plantar Fasciitis Dress Shoe Features To Avoid

The above list covers some of the characteristics you should look for in men’s dress shoes if you want relief from Plantar Fasciitis. However, just as important is to know what to avoid. Keep in mind the following:

  • Narrow Toe Box: narrow men’s dress shoes are not only uncomfortable but can also cause lasting damage to your feet. If you have wider feet, look for styles that offer plenty of room for your entire foot. If wide sizes are available, always give these a try even if you’ve never worn wide sizes in the past.
  • Leather Soles: the most expensive dress shoes tend to be crafted with leather soles. While these are classy, they can take some time to break in and may never provide the shock absorption and rigid arch support that you need to ease your Plantar Fasciitis.
  • Lack of Arch Support: perhaps by this point it should go without saying, but if you suffer from foot pain resulting from Plantar Fasciitis or another condition, avoid any dress shoe that lacks arch support or causes sharp pain, no matter how good they may look on your feet.

What Next?

Now that you have read about the best men’s dress shoes for Plantar Fasciitis, consider perusing other related guides for this condition:

"No garish orthotic shoes. Finally, I'm not wearing ugly orthopaedic shoes because of my sensitive Plantar.”
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