Sizes: 5-12, in half sizes | Colors: 9 | Materials: Leather, latex/cork insole, PU rubber outsole 

These booties are a favorite of Dr. Alvarez, who recommends them for a variety of support-friendly features. “The removable insole with built-in arch support allows for the use of custom orthotics if needed,” he says. He also likes the rocker sole, which helps reduce foot fatigue, “making it a great choice for those with high arches or plantar fasciitis.” Speaking of that removable insole—it’s crafted in a combination of latex and cork, which forms to the foot for added comfort. The booties are also designed with wide straps that sweep across the foot and fasten with a hook-and-loop closure, and they’re finished with moisture-wicking leather interiors. 

Sizes: 5-113, in half sizes and 2 widths | Colors: 3 | Materials: Leather, rubber outsole 

It’s pretty much impossible to talk about comfortable footwear and not include Vionic in the conversation. “Vionic is known for its orthopedic footwear,” Alvarez says. These podiatrist-designed booties feature the brand’s signature Vio Motion footbed, which provides an unparalleled combination of shock-absorbing cushioning, contoured arch support, and a deep heel cup for stability and flexibility. They also have seam-sealed technology to help keep moisture out, and come on and off easily thanks to side zippers and side- gores. They’re a great option for rainy fall days. 

Sizes: 6–11, in half sizes | Colors: 3 | Materials: Leather, synthetic sole

Booties that are cute, comfortable, and waterproof? I didn’t think it was possible—but, with these ones from Söfft, it most definitely is. The uppers are crafted in hand-stitched, waterproof leather, while the stacked heel provides a little extra height and style. They’re finished with back zips and cushioned footbeds for extra arch support. I’m already dreaming about wearing these with a midi dress and leather jacket. 

Sizes: 5–12, in half sizes and 2 widths | Colors: 3 | Materials: Leather, synthetic sole

Sometimes, I just really want to wear heels. While stilettos are basically a thing of the past due to my ankle, I love a good block heel—and these Easy Spirit booties deliver that in spades. It’s just a bonus that they actually are good for the feet on top of being really cute. These leather ankle boots are designed with the brand’s eFlex technology to maximize comfort and have flexible soles and insoles made with arch support. Plus, the removable footbeds let you add orthotics if necessary, so you can personalize the fit to your feet. They’re finished with side-zip closures for getting them on and off easily, too. 

Sizes: 4-12.5 | Colors: 20 | Materials: Leather, cork/latex insole

With a supremely wide color range—20, to be exact—and a stylish low profile, these Naot leather booties already had my heart going pitter-patter. But then I discovered the footbed, and I knew I was onto something special. They’re made with a blend of natural cork and latex and engineered to perfectly match the contours of your feet; they also continue to mold to your feet the longer you wear them. Done and done.

Sizes:5–10-10.5, in half sizes | Colors: 3 | Materials: Leather, cork/latex insole

I love the slip-on silhouette of these Chelsea boots, as well as their side gores, back heel tabs, and platform soles. Plus, the lavender suede hue is giving me major heart eyes. It’s really just a bonus that these booties have the brand’s iconic, anatomically-shaped cork and latex footbed, which offers custom comfort and arch support. Get ready to boot up.

Sizes: 5.5-12, in half sizes| Colors: 2 | Materials: Leather, rubber outsoles

Sizes: 5.5-6–11.5-12

Dansko has long been lauded for their clogs, thanks to their legendary heel support and roomy toe boxes. These moto boots take the brand to a whole new level, thanks to waterproof nubuck leather uppers, moisture-wicking and odor-controlling lining, a breathable sockliner, and textured rubber outsoles. Not to mention, they have molded footbeds that are designed with the brand’s signature Natural Arch technology and memory foam to provide comfort and support, and the footbeds are removable. Add in the cool buckle details and block heels, and I’m definitely sold.

Sizes: 5-12, in half sizes and 2 widths | Colors: 3 | Materials: Leather, synthetic outsole

These booties have a slender strap across the vamp that fastens with a cool, moto-inspired buckle detail. They also have low-stacked heels, which make them easy to walk in. What’s better, though, is that they’re designed with the brand’s Cushion Soft technology, which features high-rebound foam inlays concealed inside the boots to help absorb the impact with every step you take. Clarks is a favorite of Dr. Alvarez, too, who says it’s “a brand synonymous with comfort.” Can’t argue with that.

Sizes: 6-12, in half sizes and 3 widths | Colors: 1 | Materials: Tumbled leather, EVA outsole

There’s a lot to like about these SoftWalk booties—the wedge soles, the tumbled leather uppers with inset suede heels, the cushioned footbeds, and the side ankle zips. And, yes, all of that makes for ankle boots that are as stylish as they are easy to walk in. Additionally, they have three different width options—narrow, regular, and wide—so they’ll fit a variety of feet. All that’s left to do is pair them with leggings and a T-shirt and head out for a day of errands in plush comfort.

Sizes: 5-12, in half sizes | Colors: 1 | Materials: Leather, felt

Sometimes you don’t want to deal with a lot of fussy buckles or zippers—you just want to slip on a pair of booties and head out the door. Well, that’s exactly what you’ll get with these handy-dandy slip-on booties from Sorel. They’re crafted in genuine suede that’s been sourced from a responsible tannery. They have sturdy rubber wedge heels, removable insoles, and a reinforced heel counter that make them super comfortable for trekking long distances. Plus, the elastic side gores with inset contrast felt color-blocking let you slide them on and off with ease. Game, set, match.

Sizes: 6-11, in half sizes and 2 widths | Colors: 7 | Materials: Faux, recycled suede

Now that Sarah Jessica Parker has single-handedly (single-footedly?) revolutionized Dr. Scholl’s, I’m on a mission to buy every single style from the brand. That includes these booties, which are designed with low-stacked heels and side zip closures. They come in a wide variety of versatile colors and fabrics, including faux leather, faux suede, and even all-over perforated detailing. Inside, they have anti-odor insoles, plus a ton of cushioning and support. I also love that they’re sustainably crafted from recycled plastic bottles and are even shipped in a box made with recyclable materials and soy-based inks. Looking good while doing good? Sold.

Sizes: 5-11, in half sizes and wide widths | Colors: 3 | Materials: Faux leather, synthetic outsole

When I want to add height to my five-foot frame, I reach for a pair of wedge booties. Enter, these wedges from Naturalizer, which have heels that measure just under three inches high, making them equal parts comfortable and stylish. They also feature an exposed hardware zipper at one side, a padded heel collar, an antimicrobial sockliner, and arch support with cushy memory foam. They come in black, gray, and brown—and, you know what? I want all three.

Sizes: S- XL | Colors: 6 | Materials: 

When Oprah deems an item as one of her favorite things, I sit up and take notice—which means I’ve long been curious about these slipper booties, which she picked back in 2022. The quilted nylon booties feature a durable, thermoplastic rubber sole, breathable and temperature-regulating DF Adapt technology, and they come in a variety of bold hues. They also have gel-infused memory foam insoles that offer cloud-like comfort.

Plus, they’re podiatrist-approved. “They have a relatively wide toe box and are made from a soft and flexible upper material, which is great for not pinching or restricting the toes,” Alissa Kuzinas, DPM and founder of Doctor Ark, previously told Well+Good.