Fashionable Orthotic-Friendly Dress Shoes for Men and Women

Posted by Orthotics Direct on 2020 Nov 12th

When it comes to dress shoes, men and women both know that comfort often takes a backseat to looks. If you’re wearing a snappy suit or a long, slinky dress for an evening out, the last thing you want is for your shoes to take away from your outfit.

To look dressed to kill, this may leave us wearing shoes that look great but are often uncomfortable, with minimal support that accommodates our foot health and no room for a custom orthotic insole.

In fact, in traditional retailers, finding comfortable dress shoes can be difficult.

If you have a foot issue like plantar fasciitis or metatarsalgia that requires extra cushioning in the sole, finding an orthotic-friendly shoe that can accommodate a supportive insole is difficult.

Since many shoe manufacturers make dress shoes for style rather than comfort, the average dress shoe is very tight in width and volume. They also come with very narrow, dense insoles that are made with little to no cushioning. These insoles are usually non-removable, filling up space that could have otherwise been used by an orthotic device.

Even though dress shoes for both men and women are uncomfortable and unsupportive, they remain the norm in many workplaces and on many occasions.

Today, we’ll discuss how you can search out orthotic-friendly dress shoes for both women and men, ensuring you’re both comfortable and stylish for all your upcoming events.

Our Favorite Orthotic Friendly Shoes for Special Occasions

At Orthotics Direct, we’re cautious about selecting shoe brands that provide full comfort and support to our customers. We do this by evaluating the quality and features of every shoe in our store before it’s available to our customers.

We look for support features like cushioned footbeds, removable insoles, and slip-resistant soles and ensure that every shoe we stock can accommodate a custom orthotic device.

We’re fortunate to stock some of the best comfortable dress shoe brands on the market today. Here are some of our favourites.


Clarks has been making high-quality shoes since 1825, and they’ve invested in many innovations over the years to make their shoes more comfortable. Although the Desert Boot is undoubtedly one of their more famous products, they have many pairs of comfortable dress shoes available for both men and women.

Their comfortable dress shoes for men include the UnKenneth Way, a lace-up dress shoe with hidden air circulation and padding, and the vintage-inspired UnCorner Time, an unstructured dress shoe with a padded collar and secure, lace-up closures.

For women, their UnLoop clogs are a great neutral option for a casual night out and are available in black, navy, and brown.

Cole Haan

Cole Haan is a famous brand for both dress and casual shoes. Their shoe line is a fantastic mix of classic styles like oxfords and lace-up dress shoes, mixed in with new styles and colours that give customers plenty of options to dress up.

We love their Grand Evolution Wingtip Oxfords, which come in a variety of shades, including one with a distinctive robin’s egg blue exterior sole. Cole Haan designs shoes to be lightweight, with dual-density cushioning from heel to toe. Plus, these oxfords come with Achilles heel cushioning to ensure more comfort and less irritation.


For an understated pair of orthotic friendly women's dress shoes, check out Ecco. They specialize in leather goods, ranging from boots and sandals to ballet flats and even golf cleats. Right now, we at Orthotics Direct have a variety of casual shoes and boots in stock.

One of our favourites is their women’s Soft 5 Slip-On Shoe, made with a leather upper combined with elastic panels to ensure that they’re easy to put on and take off. We also carry a variety of orthotic-friendly riding boots, including their Shape M 35 boots. The solid sole and moulded footbed provide stability, even with a 35mm heel.

We love their Biarritz shoes for men, available in low-cut lace ups, slip ons, and wingtips.


Florsheim is another trustworthy brand that’s been making comfortable shoes since 1892. They got their start in a small factory in Chicago, and since then have dedicated themselves to the creation of classic brogues, oxfords, and other dress shoes for men. Their shoes are traditional and classic in style, but they’ve still managed to include features like padded sock liners and a smoothly cushioned insole for all-day comfort.

At Orthotics Direct, we’ve only stocked Florsheim’s orthotic-friendly men's dress shoes to ensure that you’re as comfortable as possible on the go. Our favourite is the Curtis dress oxford, a fantastic option that’s as padded as possible while remaining stylish.

The Cortland is another contemporary dress oxford that’s available in a bigger diameter to accommodate wide feet.


We love Rockport, and we carry a variety of reasonably priced orthotic-friendly shoes for men and women. Their shoes are all made to fit a classic dress profile, with sensible, supportive features like EVA shock absorption along with the footbed and heel cup support.

Our favourites for men are the Charles Road Captoe, made with a smooth polished leather upper, and the Dustyn Wingtip in a gorgeous grey waterproof leather.

For women, their tall boots are a popular choice. The Copley Tall Boot is available in both traditional leather and waterproof leather.

Walk with Confidence with Comfortable Dress Shoes

Want to make sure your insert will fit into your shoe appropriately? Buy them together at Orthotics Direct!

We make all of our custom inserts to fit your exact measurements, and if you buy a package, we’ll take the time to fit your insole securely into your new pair of shoes before they leave our facility.

We offer a 100% satisfaction guarantee, no questions asked. Start shopping online today to check out more of our comfortable dress shoe options.