The Most Comfortable Shoes That Don’t Look Like Comfort Shoes – Charm

I joke that living in New York will make you an expert on comfortable shoes, whether you like it or not. If you regularly take public transit, you’ll probably end up walking at least 6,000 steps a day. My average is closer to 11,000. And I have the added joy of dealing with plantar fasciitis (which means extreme heel pain if I wear unsupportive shoes too often), so I can tell pretty quickly which shoes work and which ones will leave me limping. And while it’s not hard to find supportive footwear in general, it is if you aren’t ready to resign yourself to frumpy, orthopedic-looking styles.

I work in fashion, so I need my shoes to look as good as they feel. As an editor and an influencer, I’m constantly on the hunt for footwear that bridges that gap—i.e. “comfortable shoes that don’t look like ‘comfort shoes.’” (Scare quotes fully intended!)

Lately, a few such pairs have been in regular rotation in my fall wardrobe. Here’s how I’m styling my actually comfortable shoes for cooler weather.

The most comfortable sneakers

(Image credit: Sarah Chiwaya)

These sneakers are my gold standard when it comes to comfort shoes that I actually want to wear. Vionic is a true orthopedic brand, with strong arch support built into all their shoes—a godsend for someone with plantar fasciitis like me. I have yet to try a pair of Vionics that aren’t comfortable and supportive, but not all of its assortment is a fit for me aesthetically. To put it plainly, some of its styles look orthopedic, which is not what I’m looking for.

The Walk Max sneakers, though, are a wonderful exception. Externally, they’re indistinguishable from the casual gorpcore/dad sneaker styles that have become a fashion girl staple, but internally, they pack all the orthopedic features Vionic is known for (think scientific arch support and blissfully soft insoles crafted to fit the natural contours of the feet). They also come in a great size range (5-13), with both medium and wide width options.

Vionic

Walk Max Lace Up Sneaker

These sneakers also last. I’ve had the same pair for over three years at this point, and even though they’re a little dustier now, they’re still just as supportive (and even more comfortable than new, as they’ve molded to my feet with wear). That’s saying something, as these are my go-to style whenever I know I have a long day on my feet ahead of me, whether I’m traveling, going to a music festival, or just running around NYC from meeting to meeting. I’ve easily put a million steps in these sneakers, so I appreciate that they’re still going strong.

I’ll style them casually with a lightweight cashmere sweater, a cinched faux leather jacket, and wide-leg jeans. (Mine are from Lane Bryant, but they’re sold out.) I also love wearing this style of sneaker with scrunch socks, leggings, and a big sweater. The new brown suede colorway is just begging for a neutral monochrome moment.

Quince

Mongolian Cashmere V-Neck Sweater

Finesse

Zui Maroon Vegan Leather Oversized Cropped Jacket

Levi’s

318 Shaping Wide Leg Women’s Jean

The most comfortable boots

When it comes to tall boots, comfort isn’t just about the sole—it’s also about the fit of the calf. As someone who often is sized out of even ostensibly “wide calf” boots, I know all too well the pain of trying (and failing) to squish into too-small boot shafts. And even if I succeed, there’s nothing comfortable about feeling like my calf muscles are being slowly strangled throughout the day. This plight is often exacerbated by the fact that most actual wide calf options are made of synthetic faux leather that doesn’t comfortably break in with wear.

I’ve been on a mission to find luxe, real leather boots in wide calf for a least a decade now, and have found some great options in the last couple of years, including new extra wide calf offerings from Dolce Vita and Naturalizer, and even some beautiful options from independent designer labels like New Amendment. However, I have never worn one pair so much as I have my first pair from Duo Boots.

DuoBoots

Haltham Standard Shaft Knee-High Boots in Black Leather

I tried this style for the first time in early October, and have since worn them more times than I can count. They feel like the Platonic ideal of a leather riding boot: sleek, chic, versatile, and made from beautiful, supple leather. Being able to zip them up with ease—zero struggling or squishing required—makes them even better in my book. And they aren’t just a perfect fit for my calf size: This style comes in nine different calf widths, from narrow (starting at 11.8”) to true wide width (20.9”). I tried the 19.7” boot, and it fit beautifully out of the box. It’s still looking pristine 10+ wears later, but I might even go one calf size down on my next pair, as the buttery leather definitely conforms to the leg with wear.

The inclusivity doesn’t end with the calf widths, either. Many Duo styles, including this one, come in both petite and tall heights in addition to the standard.

The artisan-crafted footbed is incredibly comfortable too, even for long days of walking, which is a big part of the reason they’ve become such a fast favorite of mine. I’ve styled these so many ways just in the month or so I’ve had them. The sleek leather silhouette looks just as sharp peeking out from under a skirt as worn with a mini. I paired them with a pleated, Issey Miyake-esque column dress from one of my favorite plus designer labels, Cynthia Vincent’s Baacal, a past season moto jacket from Tamara Malas, and a crossbody bag by NYC designer Min & Mon.

Baacal

Jaya Pleated Dress

Eloquii

Faux Leather Moto Jacket

Min & Mon

Verto Black Leather Crossbody Bag

The most comfortable mules

If it takes a lot of work to find shoes that are cute and comfortable in general, then you know it’s a struggle when it comes to on-trend styles (especially if you aren’t looking to spend over $500 on a pair). Ones from fast-fashion brands are often a one-way ticket to foot pain, and full-on “comfort shoe” brands usually aren’t at the forefront of current fads.

Take this season’s minimal mule trend: I recently found myself looking for a new black leather pair after my cat’s untimely destruction of my go-to Andre Assous mules. I wanted clean lines, soft leather that will get better with wear, and true walkability. I found that all in one pair from Franco Sarto.

Franco Sarto

Nicola Square Toe Mule

The square toe on these is particularly good, both for aesthetic and comfort reasons (no toe pinching!). I walked about 8,500 steps in these on my first wear, and even with the new shoe breaking in period, these were comfortable. (And I know from my experience with the brand that they only get better with wear.) The sculptural wedge heel feels sturdy and supportive, and I love the look of it.

For a weekend look, I styled these casually with Madewell jeans and my beloved Fashion Brand Company Dueling Horses jacket. This pair looks great with so many denim silhouettes, as well as wide leg trousers and a perfectly fitted tee. I’d also wear them peeking out from under a fitted maxi dress with a voluminous bomber jacket on top.