The grand majority of our clients have foot issues.  Figuring out how to work around these issues is just a part of my job.  It’s part what always makes me chuckle a bit when people tell me they want to be a stylist or who assume my job is glamorous.  They neglect to realize that the average woman who hires a stylist comes to the table with a litany of dressing requirements that can tricky to navigate.  Even after 21 years of being in business, I am still encountering unique challenges, but, foot issues, this is incredibly common.  

Working around foot problems is incredibly frustrating.  Aside from the discomfort, figuring out how to dress in a way that doesn’t highlight the fact that you have been relegated to functional, comfort shoes can be daunting.  How do you make your looks work and look purposeful with such a small selection to choose from?  

The one, and most common way to go about it is to think outfit first, shoes second, meaning that a lot of looks are built in a way where the shoes look out of place because they don’t technically belong with the outfit.  The second way, and the way I prefer is to think shoes first, outfit second.  If a client has foot problems, I consider what shoes they can wear and then build around that.  For example, if a silhouette only works with heels, this is a silhouette I will keep out of their wardrobe.  While this may seem limiting, it works a lot better than putting the wrong shoes with the wrong silhouette.  With my approach, outfits look more purposeful and, more importantly, don’t highlight the fact that your shoes are made from necessity.


I have put together different looks for work using comfort shoe brands that help a variety of different foot issues to show that a look doesn’t have be sacrificed due to shoes designed with comfort in mind.


I am currently working with two clients who have found comfort in barefoot shoes, also known as minimalist shoes.  Barefoot shoes are footwear designed to closely mimic the experience of walking or running barefoot while still providing some degree of protection from the elements. These shoes typically have thin soles and little to no arch support or cushioning, allowing the foot to flex and move more naturally.

The idea behind barefoot shoes is to promote a more natural gait and foot movement, which proponents argue can lead to stronger feet, better posture, and reduced risk of injury. Some barefoot shoe designs feature a wide toe box to allow the toes to spread out naturally, which is thought to improve balance and stability.

While some people find barefoot shoes comfortable and beneficial, they may not be suitable for everyone, particularly those with pre-existing foot conditions or who are accustomed to more supportive footwear. It’s important to transition slowly to barefoot shoes to allow your feet and muscles to adapt gradually.

My one client and I have spent a few sessions working her wardrobe around barefoot shoes, and one of my clients bought this pair from Origo after struggling to find shoes that worked for her feet.  This pair can work well with long maxi skirts, along with a variety of pants and jeans.  In this look, I styled the shoes for work with a pair of Everlane pants, a silk blouse from MM. Lafleur, and a blazer from Rails. I finished the look with a cognac belt from Nordstrom and knot studs from Bony Levy.


Shoes like clogs have a rocker sole bottom which is known to provide benefits like reduced pressure on the joints, a more even distribution of pressure across the foot, which may reduce strain on the ankles, knees, and hips which would be particularly beneficial for individuals with conditions such as arthritis or joint pain.  Rocker soles also provide improved stability. The curved sole of rocker sole shoes can enhance stability by promoting a smoother gait and reducing the risk of tripping or stumbling. This can be especially helpful for older adults or individuals with balance issues.  Another benefit is enhanced walking efficiency. Rocker sole shoes facilitate a more natural walking motion, which can lead to improved walking efficiency and reduced fatigue over time. Rocker sole shoes are sometimes used in rehabilitation settings to help individuals recover from foot or ankle injuries. The rocking motion can assist in strengthening the muscles and restoring normal foot mechanics.  Rocker sole shoes may provide relief for certain foot conditions such as plantar fasciitis or metatarsalgia by reducing pressure on specific areas of the foot and promoting better alignment.

I have one client who almost exclusively needs to wear clogs.   In this case, my goal has been to make these shoes almost invisible in her looks.  Another strategy is to abandon the clog look entirely, because I think we can all agree, they don’t work across the board, and choose a style like this, also from Dansko.

Purposefully, I chose a beige style from Dansko that doesn’t draw attention and selected a style of dress for work from Argent that works with the shoes.  It would never pair these shoes with a professional skirt suit, for example.  I finished the outfit with chunky square hoops from Madewell.


Needing to work orthotics with shoes creates a huge obstacle when choosing shoes because you need to look for styles that provide the necessary support and accommodate the inserts comfortably.  While there are orthotics for heels which are usually thinner and more streamlined compared to traditional orthotics to fit comfortably in narrow or tight-fitting footwear, it can’t be ignored that most people who need orthotics can’t really wear heels in the first place.  There is also the issue of finding flat shoes that fit traditional orthotics.  Not easy and as a result, the selection pool gets quite shallow.

Casual footwear like sneakers, loafers, or casual boots can also work well with orthotics, especially if they have removable insoles or extra depth to accommodate the inserts.   Some dress shoe brands offer styles with removable insoles or extra depth to accommodate orthotics while maintaining a professional appearance.   When trying on shoes with orthotics, it’s essential to ensure there is enough space to accommodate the inserts without causing discomfort or crowding.   Another issue that is seldom talked about is the instep of shoes when wearing orthotics.  Even with enough heel depth for orthotics, a foot can slip out if the instep doesn’t have enough coverage.

In this look, I styled these shoes from Naot, which have a removable insole so orthotics can be inserted.  There is also a substantial instep support to ensure the foot will be secure in the shoes.  I created this business casual outfit with these burgundy pants from Elie Tahari and a layered turtleneck sweater from Brochu Walker.  I finished the outfit with linear earrings from Karine Sultan.


foot issues

Over the years, comfort shoe brands have come a long way.  For sure, it used to be a much bigger compromise if you had foot issues.  Take, for example, this metallic loafer from Vionic, they hardly scrimp on style.  Vionic, for example, is designed with built-in orthotic technology featuring contoured arch support. This arch support helps align the feet to their natural position, reducing overpronation.  They also incorporate cushioned footbeds made from materials like EVA (ethylene-vinyl acetate) foam or memory foam. This cushioning helps absorb shock and provides additional comfort, especially during extended periods of standing or walking.  With a deep heel cup many Vionic shoes have a deep heel cup designed to cradle the heel and provide stability. This feature helps distribute weight evenly and reduces pressure on the heels, which can alleviate discomfort and prevent issues like plantar fasciitis.

I styled this suited look with the Vionic metallic loafers using these pieces from MM. Lafleur (link to blazer, link to pants), and a striped tee from Boden.  I finished the look with red earrings from Ralph Lauren.


foot issues

You may be wondering what business a pair of heels has being here, but in this case, I chose shoes from bunions.  While heels aren’t always best because they exacerbate bunion pain by forcing the toes into a cramped position, I have had clients with bunions choose heels.  What is important in this case is to look for shoes with a wide toe box to accommodate the bunion comfortably without putting pressure on it. Shoes with a wider width can help prevent rubbing and irritation on the bunion.  It’s also important to choose shoes made from soft and flexible materials that can adapt to the shape of the foot and provide gentle support without causing friction or irritation.  

This is why I chose this pair of heels from Vivaia.  The heel height isn’t that high which won’t force the foot forward as the flexible knit fabrication of the shoes allows for room for bunions.  I styled the shoes with this dress from BOSS Hugo Boss, a white blazer from Favorite Daughter, and finished the look with a colorful beaded necklace from Chan Luu.


Having foot issues is incredibly common and while it can be disheartening to have to work your clothing choices around the needs of your feet, it does not mean you have to sacrifice the way you look.