Best Dress Shoes for Women with Heel Pain – Stylish and Supportive!


Are you looking for a pair of dress shoes that are stylish and supportive at the same time? Do you have a special occasion coming up such as a wedding or do you need to wear closed toe professional dress shoes to work? I am going to show you a list of the best dress shoes for women with heel pain based on my many years of shoe fitting experience.

Have you already tried several methods to reduce your heel pain such as taping, stretching, resting, and cortisone shots as well?

My Experience Helping Women with Plantar Fasciitis

I am not a medical professional, but I have helped hundreds of women with heel pain find the perfect pair of dress shoes for their feet, and I am sure I will be able to help you too. Some women in addition to having heel pain have “complicated” foot shapes such as long, slender toes, high arches, high insteps, a wide base, or a narrow short heel… you name it! Some other women who visit the shoe store had short toes, flat feet, and quad heels!

Do you literally live in your sneakers with custom orthotics and your feet still hurt? Many of the women that I speak to complain that many of the dress shoes made for problem feet look like shoes their grandmothers would have worn. They are always asking me to find her dress shoes that aren’t specifically made for problem feet, but are supportive enough for them to wear.

What Makes the Dress Shoes that I Recommend Ideal for Women with Heel Pain?

1️⃣ Substantial and Supportive Outsoles: The dress shoes that I recommend provide a substantial and supportive outsole that will help cushion and support your feet. This will help reduce your heel pain. Take a look at the image below for better visualization purposes:


2️⃣ Firm Heel Counters with Targeted Heel Support: The dress shoes that I recommend also provide firm heel counters (back part of the shoe) with targeted support right below the heels. This feature will also help prevent foot and heel pain. Take a look at the image below for better visualization purposes:


Are Mary Jane Shoes More Supportive Than Flats or High Heels?

Yes, women who experience heel pain can strongly benefit from wearing a Mary Jane dress shoe style. The advantage of Mary Jane dress shoes over other types of dress shoes is that certain Mary Jane shoes provide a more substantial and supportive outsole. They also provide extra cushion and support right below the heels (only some specific styles).

Make Sure You Know Your Exact Foot Size!

Did you know that 88% of American women wear the wrong size of shoes? The American Orthopedic Foot and Ankle Society revealed this appalling information!

Your feet need to fit comfortably. Wearing the wrong size shoe can lead to foot problems. You also need to be aware that your foot shape and size can change over time. This can happen due to weight gain or loss, pregnancy, aging among other reasons. The ligaments and tendons also lose strength due to aging and make your arches decrease which can flatten and lengthen your foot and toes. 

You should get your feet measured every 6 months. Be aware that when looking for your shoe size you have to look at the length but also the width! Quality measurements start with expert consultation, so let me help you find your exact foot length:

How to Measure Your Foot Shoe Size – The Most Simple and Effective Way!

It is always advisable to visit your local shoe store to get a proper shoe fitting if that is possible. However, if you don’t have any near follow the instructions on the previous link!

The dress shoes that I recommend below are the ones that I have fitted at the shoe store, but some models that I recommend are from personal research that I did on the Internet. Some recommendations are also from women who already tried the dress shoes and experienced significant relief from their heel pain. Disclosure: Keep in mind that we may receive commissions when you click our links and make purchases.

Best Dress Shoes for Women with Heel Pain

Take a look at the description below each dress shoe that I recommend to find out if it can accommodate your foot shape, the materials that the dress shoes are made of, and the size you should order to prevent your longest toe from rubbing against the front part of the shoes.

It’s important to keep in mind that even though these dress shoes have worked well for many women with Plantar Fasciitis, they might not work as well for others! Our feet are like snowfalls, no two are alike.

What Shoe Size Should You Order?

To prevent your toes from rubbing against the front or side part of the shoes, I highly recommend that you order the shoes a whole size larger than your current foot size. This translates to 3/8 of an inch or 0.8 centimeters of space between your longest toe and the end of the shoes.

Would You Rather Get Specific Shoe Recommendations Based on Your Foot Shape?

If you tell me your foot shape (narrow, medium, wide, extra wide), the degree of your foot condition, and the country that you are contacting me from I can provide you with specific shoe recommendations. You can contact me via email:

Should You Fit an Orthotic Inside the Dress Shoes that I Recommended?

I suggest that you first try the dress shoes without any orthotics and give it at least a month before you decide to fit an orthotic for extra support. If after wearing the dress shoes for a month you still experience pain and believe that you can benefit from wearing an orthotic, simply remove the original insoles of the dress shoes and place your orthotic inside the shoes.

If you are unsure about which orthotic works best for helping treat Plantar Fasciitis I suggest that you take a look at the article below:

Best Orthotic for Women with Heel Pain – Targeted Cushion and Support Right Below Your Heels!

Additional Resources for Women with Plantar Fasciitis

Are you always in search of the perfect shoe? I have created many resources for women with heel pain. Some of the most popular ones are:

The Best Women Walking Shoes for Plantar Fasciitis – The Proven Method to Treat and Prevent It!

The Best Women’s Sandals for Plantar Fasciitis – Supportive, Lightweight, Flexible and with Extra Heel Support!

I have noticed through the years that most women’s foot and leg pain is directly associated with the shoes that they wear. There is a tendency to worry a lot when you are experiencing any sort of pain, but the good news is that something so simple such as wearing the correct shoe style and the correct shoe size will greatly reduce or fully eliminate the pain that you are experiencing.

What are your go-to dress shoes recommendations for women with heel pain? Have you found a specific shoe brand or shoe style that worked well for your feet? Share your findings in the comments section below so other women can benefit from your experiences!

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Shoe Sizing Chart

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