Styling Sensitive Feet

By Audi, Already Pretty Contributor

When it comes to shoes, comfort and style seem to exist on inverse sliding scales. I’ve found plenty of comfortable shoes that look perfectly fine, but very few that I love equally for the look as I do for the feel. Because I love shoes but also have very sensitive feet, I put a lot of effort into selecting, styling, and strategizing my footwear.

The Elusive Cute + Comfy

The big wins will obviously be scored when comfort and style are present in equal measure. Here are a few styles I’ve tracked down that I consider to be superior in comfort while also looking great. You won’t see anything red carpet-worthy here, but for most of us they’ll fit the bill for a day at work or running errands. There are a few more suggestions at the bottom of the post.

1303218-p-MULTIVIEWThe Dansko Veda is a clog cleverly disguised as a sneaker. They have all the support of the classic clog but are adjustable across the top of the foot thanks to the laces. They come in several colors (including plaid!), have an insole that’s easy to remove and replace, and they’re even vegan. This is a true all-day-on-your-feet shoe.

2301821-p-MULTIVIEWI sung the praises of the Clarks Valley Lounge in my last post, and I’ll sing them again. Smoking flats are very on-trend, and this style has plenty of cushioning inside to provide support and keep the shoes from slipping and rubbing. When you can’t wear heels, an eye-catching flat is a great alternative.

2352601-p-MULTIVIEWWedge sneakers have been a revelation for me; they have a cool streetwear vibe, offer great support and adjustability, and generally have a moderate heel height. I love these classy beauties by Geox.

2478396-p-MULTIVIEWHow fun are these? I own the Cole Haan Gramercy Oxford in navy, and they always bring the compliments. This rose gold pair is another style that offers that rare pairing of chic and comfortable. They run narrow, but sizing up half a size solves the problem.

2380716-p-MULTIVIEWAdmittedly, the Softspots Marsha style is on the plain side. But they feel fabulous, come in several different colors and in wide widths, and would be great candidates for my next tip…

Try Some DIY


Boring shoes got you down? Good thing there are approximately 2.5 million ways to embellish them. Pinterest alone has page after page after page filled with ideas and instructions for adding bows, chains, studs, flowers, glitter, jewels, and even leather panels (see above) to that comfy-but-slightly-dull pair. Image courtesy of SwellMayde.

Making Adjustments

For those pairs that have all the style you want but are aren’t quite there comfort-wise, there are plenty of options for making adjustments. Try pulling out the existing insoles and putting in more supportive ones, adding heel liners or ball-of-foot pads, or using shoe stretchers (or having them stretched by a cobbler) to fine tune the fit.

Developing a Shoe Strategy

Even if you’re not dealing with chronic foot pain, it’s often helpful to strategize when it comes to selecting the day’s footwear. Here are some elements to a good shoe strategy:

Consider what the day has in store. The higher the activity level and more challenging the weather, the more you should design your outfit around the shoes.

Avoid wearing the same shoes day after day. Alternating shoes allows you to use different muscles in your feet and calves, and also gives the shoes time to air out. If you wear heels one day, make sure you switch to a flat the next.

Have a backup pair. Heels in particular really shouldn’t be worn all day and all night. After-work drinks or a parent-teacher meeting can keep you in the same pair of shoes for many hours, so for extra-long days bring along a pair of flats to change into. It’s also a great idea to keep an extra pair at work in case of emergencies.

Give them a trial run. I find that the same shoes will feel different from day to day, so I always put on my shoes at least 20 minutes before leaving the house. That way if there’s any discomfort, I find out while there’s still time to change.

Bringing Home the New Babies

Whenever I buy a new pair of shoes I have to resist the urge to wear them immediately, because I’ve learned the hard way that this can lead to a shelf full of pairs that never get worn. Whether you shop online or in a store, make sure you understand the return policy, and then play with your new shoes at home for a few days before you commit. We all know that comfy shoes can often be awkward to style, so try putting together a few outfits and making sure those mary janes can actually be worn with dresses, not just in theory. Shoes that have been worn outside generally aren’t returnable, so make sure you do a lot of walking indoors, especially on hard surfaces, to get a true idea of the comfort.

It’s Not Always About the Shoes

If you deal with foot pain, you’re sometimes going to be stuck with shoes that just don’t have the wow factor you’d like. Having limited options for shoes has inspired me to become a bag gal, because a great way to counteract plain shoes is with a killer bag. An oversized tote, structured satchel, or vibrant clutch can be the star of the show, taking the emphasis off the shoes. Bags offer all the possibilities for personal style that shoes do, without having to meet the exacting comfort demands of feet. If you want to keep the emphasis on the bag, look for eye-catching details such as patterns or colorblocking, shiny hardware or studs, interesting textures such as embossing or calf hair, or contrast topstitching. If lots of details aren’t your thing, look for bags with unique shapes or bright colors.

Over to you: how do you style those less-than-thrilling comfort shoes? Any styles to recommend that are as stylish as they are comfy?


Shown above, left to right: Wolky Dazzle, Cobb Hill Lola, and Sofft Whitney

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Audi is a biotech professional in San Francisco, California. Her blog, Fashion for Nerds, was born out of the frustration of feeling as if science and fashion were doomed to be forever divided. Through her blog she discovered she wasn’t the only one who believes that style has its place even in a scientific workplace; over the years she has met countless other women who struggle to prevent their love of fashion from hindering their credibility as technical leaders. Now in her mid-forties, Audi particularly enjoys testing the boundaries of “age-appropriate” dressing and thinks most style rules were made to be broken. Another important influence on her style is the problem of chronic foot pain, an issue which is exacerbated by San Francisco’s hilly streets and one that she is resolved not to let defeat her obsession with great looking shoes.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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8 Responses to “Styling Sensitive Feet”

  1. NancyV908

    This is a great post. Thanks. However, I think comfort is often also tied to the larger cultural issue of heels–specifically, high heels. A little height is one thing, but often “stylish” means very high heels. They’re painful, yes, and also bad for your health. How many women have chronic pain from wearing heels? Or just short-term pain at the end of the day? That’s bad enough. (Not to mention, I notice that women often look terrible when they walk in high heels, particularly skinny heels–they’re off balance, so they have a very unnatural, clunky gait, which totally counteracts the sexy look they’re supposedly going for.) I mean, look at the previous post, on jeans–check out the shoes on the models. High, skinny heels. Even wedges or more “sensible” high heels throw you off balance. I wish that shoes that didn’t make your feet ache or cause chronic problems would be considered stylish (or appropriate for settings where high heels still rule), and that more women would resist the pain and damage that high heels can cause. Apologies in advance to the high-heel-loving among you–I know many of you manage fine in them. But I just feel that it would be nice if other alternatives were considered stylish. This has been on my mind because my 17-yr-old stepdaughter wants boots with superhigh spiky heels. I don’t know if she could even stay upright in them; she’d certainly be putting her entire weight on the balls of her feet. But it bothers me that she thinks that look is sexy–or that sexiness is worth the pain of shoes like that.

  2. Linda L

    Great post, Audi. I have those rose gold Cole Haan’s (and a boatload of other Cole Haan’s) and they are fabulous. Even men compliment me on them.

  3. Emily Stowe

    Within the past year, I have discovered that knee high boots are the most comfortable option for me to wear with skirts and dresses. I have wide, flat, turned out Diabetic feet that just have a hard time being comfy in anything cute. Plus, they are big- size 13. I found extra wide width and extra wide calf boots at Avenue, and bought up pretty much every style of flat-heeled ones! I also swear by my Crocs Santa Fe Rx shoes, they are men’s sip on black shoes with a totally fabric upper, so they are comfy immediately, with no breaking in- the fabric prevents any blisters. They are very plain, which makes them perfect for blending in to black dress pants or jeans. I found them cheap on sale recently and bought two more pairs!

  4. Aya in Couturgatory

    Hey, I own that top Dansko pair! Found ’em in the thrift shop in the Outer Sunset. I feel fashionable now. 😀

    I like Hush Puppies extra wide shoes for my bear claw shaped feet. I can’t take any heels taller than 2.5″ and since my toes splay out and I have a high instep, I’m very sensitive to narrow toe boxes.

  5. Alison

    I just ordered the Clarks leopard shoes thanks to this post! FYI they’re cheaper in some sizes on Amazon and have Prime free shipping available; also if you go through Ebates you get 4% cash back! Thanks Audi and Sal!

  6. Jean S

    I’m dealing with plantar fasciitis right now, so this strikes home. I’m going to have to go through my shoes in January and evaluate each and every pair, then think about replacements.

    There are some lines out there that I like–Ecco, Beautifeel–but they can be pricey. So it goes; it will force me to really think through my purchases.

  7. AmyAnyman

    I also own those Danskos! I bought them before taking a vacation to a theme park, because I knew I’d be walking for miles, all day long. They did not disappoint.