How to Choose Comfortable Dress Shoes 

Elevate your outfit with a pair of stylish dress shoes that not only look great but feel comfortable. With features like extra padding, soft leather, arch support, and supportive straps, these shoes won’t give you achy toes or legs, even after a long day. Whether you’re shopping for a corporate wardrobe, are heading off on vacation and want a pair of versatile kicks, or have a special occasion coming up, you don’t need to pick between comfort and style.

How to Choose Comfortable Dress Shoes 

There are a few factors to consider when purchasing comfortable dress shoes. Of course, you want them to look nice and to feel beautiful wearing them. However, for true comfort, you’ll also need to consider other elements like style, occasion, size, materials, and arch support (which is especially important if you already have issues such as bunions or plantar fasciitis).

Pick The Right Style 

Choosing comfortable dress shoes is about more than just the looks — choosing the right style is essential. Enclosed shoes like pumps are good if you need all-around support, while the strap on Mary Janes holds you in even more. If your balance is an issue, flats or block heels will be much more stable than stilettos. Of course, oxfords, loafers, and boots offer full foot support, but sandals might be a better choice if you find your feet overheat and sweat easily.

Check Your Leathers 

Leather shoes are great because they are breathable and will mold your foot shape over time. The better quality of the leather, the better the feel will be. However, the price will also go up. If you are looking for leather shoes, make sure to check that both the lining and the outers are leather — some manufacturers will sometimes opt to use synthetic materials on one of the layers, which can affect how a shoe wears. A leather shoe can also look much nicer than alternatives because they develop a beautiful patina over time as you wear them, adding elegance and character to a shoe.

Don’t Ignore Arch Support

Arch support in shoes is a major contributing factor to comfort levels. As such, don’t ignore this feature. Adequate arch support can help with conditions such as flat feet, overpronation, and plantar fasciitis. Good arch support also keeps your legs, hips, and back aligned, which can lead to pain and fatigue when misaligned — especially if you spend a lot of time on your feet. If you do already have foot issues, you might have prescription orthotics. Many shoes designed for comfort have insoles or arch support that you can remove and use your own custom-made inserts instead for an even better fit.

Know Your Shoe Size 

Shoe sizes vary from country to country, with different labeling systems in place in the United States, Europe, Asia, and Australia. Knowing the conversion between the sizing is important, so you always get the correct fit. If you’re shopping online, it’s also a good idea to check the sizing charts and read reviews or product descriptions to see if individual styles run large or small. Finally, some shoe designs come in different widths so that you can tailor the fit even better. Don’t be afraid to trace your foot on a piece of paper and measure the width and length so you can choose the best fit.

Keep Your Intended Event in Mind 

Picking the right shoe for the right event is essential. A pair of killer heels are fine if you work behind a desk all day. However, if you’re on vacation, you don’t want to walk for miles in high shoes and ruin your fun with sore feet. The same goes for shoes that pinch or rub, don’t provide the proper support, or don’t fit your feet particularly well. In addition to keeping the event in mind, you’ll also have to consider how you get there. Walking and taking public transport will likely mean you’ll need to consider a more practical option than if you’re getting dropped right outside the venue.

Dress Shoes for Different Foot Types and Foot Problems

Feet come in all shapes and sizes, which can make buying the perfect shoes a little challenging. Additionally, there are some common foot problems that can add extra complexity to the decision. This can include flat feet or high arches, wide feet, or painful conditions such as plantar fasciitis, heel spurs, bunions, and back pain. However, once you pick the right shoes, you’ll be very comfortable and can even eliminate some of the problems or at least their symptoms.

Dress Shoes for Flat Feet

Flat feet is a condition where your arch either collapses or rolls in completely, so the whole sole of your foot touches the ground. This can occur with age, unsupportive footwear choices, wearing high heels, or it can be hereditary. It’s not necessarily an issue itself, but it can put extra pressure on your ankle joints and cause pain throughout your legs and body from compensating for an altered walking pattern. Supportive gym shoes are generally the best option for flat feet. However, when it comes to dress shoes, look for quality support through the arch, heel, and sole. Wedges are a great alternative to heels that help distribute your weight more evenly. Finally, arch support insoles are also a good option.

Dress Shoes for Plantar Fasciitis

Your plantar fascia is a ligament that runs along the bottom of the foot from the toes to the heels. When this is damaged or strained, it can cause stabbing pain in the heel, known as plantar fasciitis. The best way to combat the symptoms of this condition is with shoes that have good heel and arch support. As such, look for padded footbeds with built-in arch support or styles where you can add your own. Closed-in heels are also better, so avoid styles such as sandals for long periods. Additionally, look for reinforcement through the midsole (such as with a shank) for stability, and secure closure, such as straps or laces to hold your foot in place.

Dress Shoes for High Arches

On the opposite end of the scale to flat feet is high arches. People with high arches tend to put more pressure on the outside edge of their foot and are more prone to rolling an ankle. Without the proper shoes, they can also develop knee and hip problems. When shopping for dress shoes for high arches, look for soft insoles and supportive midsoles. High arches also generally need a little more room through the midfoot, so look for a more spacious design or something adjustable such as laces or buckles. Finally, sufficient space in the toe box is also essential for ensuring your toes have room to move.

Dress Shoes for Back Pain

While there are many potential causes of back pain, wearing the wrong kind of shoes can be one of them or can exacerbate the issue. Generally, the more supportive your shoe is, the less likely it will contribute to back pain. Look for secure, fully enclosed styles so you don’t need to “grip” with your feet and that provide proper foot alignment. You’ll also want good shock absorption and strategic cushioning, especially if you spend a lot of time on your feet. Play around with the heights of the heel drop, too, as different sizes can feel better or worse for different individuals. You’ll want to avoid high heels, strappy shoes, slides, and flip-flops.

Dress Shoes for Bunions

Bunions are a bony deformation of the big toe joint and cause the big toe to point towards the outside of your foot. It can be caused by many things, including ill-fitting shoes, genetics, arthritis, and your foot’s biomechanics. They can be swollen, painful, and limit your movement. Plus, it makes buying shoes tricky! When shopping, you’ll need to look for the right-sized shoes – don’t go too small. Most people have one foot bigger than the other, so shop for the larger foot and add an insole for the smaller one. See if you can get a wider-fit shoe as well to accommodate your forefoot more comfortably. Arch support can help, as can avoiding high heels. Finally, try shoes on at the end of the day when your feet are likely to be more swollen.

Dress Shoes for Heel Spurs

In addition to plantar fasciitis, heel spurs are among the most common causes of heel pain. These are abnormal bony growths that develop on the heel bone. They can be the result of injury, inflammation, or overuse. One of the main factors to look for when buying dress shoes for heel spurs is adequate padding, primarily through the heel. This will lessen the impact of each step and help alleviate pain. If you’re struggling to find a good option, you can also buy padded heel cups to place in your shoes for extra cushioning. Finally, good arch support in your shoes will also help keep your foot aligned correctly.

Dress Shoes for Wide Feet 

Just like people come in all shapes and sizes, so do feet. As such, some people have wider feet than others. Plus, your feet can widen over time thanks to genetics, pregnancy, weight gain, age, or medical conditions, so needing a wider-fitting shoe can be common. Generally, the standard width fitting for women’s shoes is a B, which translates to “medium.” However, some brands offer different width sizing that can go up to a 9 Extra Wide. If you’re unsure what width fits you best, trace your foot on a piece of paper and measure the widest part, then compare it to a size chart for each brand (there’s no singular convention for width sizing, unfortunately). Ensuring your shoe fits correctly will help you avoid other issues like bunions.

Alex Linde

Writer | Website

Alexandra Linde is an experienced writer holding a bachelor's degree in Journalism. She is the owner of Alexandra McKiterick Creative and has expertise in travel, fashion, fitness and lifestyle. Alex has previously written for Flightcenter, Travello, and Backpacker Deals.