Tested by Walking a Mile

First of all, can I just say how impressed I am with Naturalizer? Over a decade ago, I remember following my grandmother into the store while she picked out loafers that you could tell were a podiatrist’s dream. But now, you’d be hard-pressed to find anything like those orthopedic loafers on their site.

Instead, they’ve incorporated all the comfort that they’re known for into shoes that are actually cute. So while the inside of the shoe might still be a podiatrist’s dream, the outside will be trendy and chic — exemplified by the bestselling Joy Dress Sandal.

You can see how thick the padding is by just looking at it. The insole is contoured to the shape of your foot, which offers arch support and takes the pressure off the balls of your feet. The heel itself is a whopping three-and-a-half inches, but they absolutely do not feel that high when you have them on.

I knew that I needed to test these shoes because they have a whopping twenty-four thousand reviews on Amazon and four-and-a-half stars. People in the reviews rave about wearing these all night, walking miles in them, and how they feel like they cost way more than the under-$40 price tag.  Plus, they have nearly thirty colors available. 

After walking over a mile in them on one of the first warm days of the summer, I understand what the hype is about. The heel is a perfect everyday height and you can’t beat the simplicity and versatility of the silhouette. Plus, they are absolutely everything that Amazon reviewers claim them to be — super affordable and very walkable. 

However, if you’re committed to the single-strap silhouette and want shoes that will last you through every summer wedding you attend, I would still recommend our best overall pick, the Naturalizer Joy Dress Sandal. It has an almost identical silhouette, but the Naturalizer pair has far more footbed padding. Plus, the padding is brilliantly contoured to your foot. This Dream Paris pair is great for getting pretty comfy heels at a good price, but you might face some issues with the toe strap rubbing and your foot feeling fatigued if you’re planning to wear these all the time. 

Slingbacks are the style of the season and there’s no style more comfortable than this pick by Inez. It’s available in a bunch of colors — and it comes in narrow, standard, and wide fits.

Inez is one of our favorite brands ever for comfortable heels — which is why you’ll find a bunch of their shoes on this list. In our Inez review, we raved about the brand’s commitment to only the highest quality of craftsmanship. They are made in Spain and have proprietary plush insoles, which you can absolutely tell make a huge difference. When you slip them on, you can feel immediately how they cradle your foot for maximum stability and comfort.

The Mia slingbacks, especially in the beautiful orchid color, got me tons and tons of compliments. I cannot recommend them enough.

Even if you’re a pump enthusiast, you probably haven’t felt pumps like these. Ally’s shoes feel custom since they’re available in four (yes, you heard right, four) different widths. And you can absolutely feel what a difference it makes to have a shoe in your exact size. 

I took Ally’s fit finder quiz to nail down which width would fit me best and was blown away when I received the shoes. Inside, there are layers of padding that perfectly cradle the arch of my foot. And there’s even toe box contouring to support the balls of your feet. Seriously, these have all the comfort bells and whistles that you could ask for. 

The only drawback of these is that they’re a touch expensive, but compared to actual custom shoes these are a steal.

I wore Vivaia’s lightweight wedge sandals to walk across miles of hot concrete, and the ventilated cushions were so plush that I forgot about the metatarsal pain I usually get from wearing heels. I also wore them around the pool, and the padding dries quickly after you slide into them with wet feet.

Plus, their non-slip soles make it safer to step through puddles.The stretchy knit strap caused some friction around my pinky toes when I was first breaking these in, but it subsided more and more with each wear. And while the toe area is flexible and soft, the rear is rigid for better stability.

I have narrow feet and wear a size US 8, and these fit me without sliding off. They have wide, stretchy straps to fit comfortably around feet of different widths and arches. If you feel your toe shape fits better in a square-toed sandal, Vivaia makes a similar wedge called the Laura. —Gabrielle Chase, associate style editor

Yes, that’s right, these are Crocs. They’re made of the same lightweight, foam-like material that made the clogs famous. And if you’re wondering if they feel the same; they really do. 

Like the clogs, the Brooklyn Heel footbed is cushioned and has bumps on it that are like little massage beads. At first, I was dubious about this feature, but I like how the little bumps stop my food from sliding around. And they’re lightweight like the Crocs clogs, too. 

These chunky heels lean into the ’90s vibes and give you a full extra three inches of height. Plus, unlike other chunky heels, these don’t feel like you’re lugging around rocks on your feet. And they’re just cute. I really enjoyed shocking my coworkers by telling them I was wearing Crocs. 

The only issue I foresee with these is scuffing. I got the Brooklyn Heel in white, so it’s hard to not get little black marks on them. If I were to do it again, I would probably get the black color to avoid this issue. 

If your office dress code is a little more formal, these pumps will be your new best friend. They pair perfectly with the best suits for women or formal work dresses.

The All Occasion Heels from Antonia Saint New York have an internal cushioning system that surrounds the whole foot rather than just padding the footbed. I love the comfort and, crucially, the support this offers. Instead of sliding around, my foot is firmly braced by the shoe. This is especially helpful for safety since instability can cause ankle injuries.

Usually, I size down a half-size in pumps because the pitch of the heel tends to push my toes deep down into the toe box, leaving extra space at the back. But I opted not to size down in these, and I’m glad I did. The brand’s proprietary SoftSurround System keeps my foot enveloped in foamy support so my toes don’t slip down.

The shoes are also made from soft, shiny leather that looks great and photographs well. The brand also claims that the heel is made from materials that won’t nick. I know I’ll be wearing these a ton, so I’ll report back if I experience any damage, but so far, so good!

These wavy-soled flatforms are over three inches high, so they’re one of the more towering options on this list. But they absolutely don’t feel like it. 

The wavy heel is unique and adds a ton of visual interest. Plus, because it is so thick and rubbery, it functions beautifully as a shock absorber. I can walk for miles in these without feeling the fatigue in my feet. In fact, the only shoes I can think of that do shock absorption better are Dansko clogs, which are a favorite of professionals like nurses.  

I also really appreciate that the leather upper is so long. It helps secure the rubber platform to your feet, giving you confidence that you won’t accidentally kick off your shoes with a particularly vigorous stride. It’s also flexible and comfortable. 

As far as fit, I just wish that these shoes came in half sizes. I got it in a seven but I think it would have been perfect in a six-and-a-half.

I’ve already touted the supreme comfort of Naturalizer heels and these are another stellar option. 

Not only is the footbed padded, but the straps are also cushioned. In fact, the toe strap is downright foamy. It makes a huge difference when you’re walking since the repetitive motion can make typical straps cut into you. 

I also appreciate the stability of the kitten heel. Sometimes, heels this this make you feel slightly wobbly. But these are secure and I feel sure-footed, even when walking on uneven surfaces.

If you want heels that are actually comfortable, ask podiatrists. Frankie4 was founded by a team of podiatrists who created their proprietary footbed that is designed to offer support throughout the foot, help with alignment, and absorb shock to prevent foot fatigue. 

I have these in Camel Weave — and they’re the perfect leg-lengthening flesh tone for me. These are one of the pairs that I wear the most often because of their manageable height, neutral color, and all-around comfort. I even paired them with silk pants and wore them to the airport, which is a huge testament to their walkability.

There’s just something so nice about having a pair of heels like this. They’re two inches high, so they give you a little bit of height without looking like stilts. The mule style is also so versatile and just casual enough. You can wear them to work, with jeans, on the beach with linen pants — anything goes with these shoes.

At nearly four inches with a three-inch pitch, these shoes look a little intimidating — but don’t let that fool you. They’re super lightweight, with a cushioned insole and a thick strap that wraps around your ankle for stability. 

When I wore them for the first time, I was blown away by the construction. This is a true stiletto heel. And yet, I didn’t feel any of the discomfort of basically walking around on my tippy-toes for hours. 

It’s a little on the pricier side, but it’s a perfect choice for a wedding — whether it be yours or one you’re attending as a guest. It has the rare combination of being a classic, formal stiletto while also being a shoe that you can dance in all night. 

Just not that when I first tried this, I had buckled it too loosely around my ankle. It felt much less comfortable because my foot was wiggling around too much. Make sure you fasten these on tightly (even tighter than you think you need to) for the best fit.

Vivaia remains a consistent favorite for the most comfortable footwear because of the stretchy elastic material that the brand uses. The knit upper, made from recycled plastic bottles, is much more pliable than other textiles like leather or canvas. So rather than suffering it out to break in a pair of leather slingbacks, you can slide into these immediately like a good pair of leggings.

I love how stretchy yet secure these feel. The back strap is adjustable, which is a fantastic feature to have in slingbacks. And because I could tighten it, I didn’t have any issues with accidentally stepping out of the shoe or any discomfort caused by my foot moving around in the toe box. Slingbacks, more than any other shoe, are prone to these snafus — but not the Addison Slingback Sandals from Vivaia.

Vivaia has made lots of our guides to the best footwear, including the best walking sandals for women and the best loafers for women. For a full list of our favorite styles, see our Vivaia review.

If you haven’t heard about the miracle of clear heels, allow me to educate you. There are certain features of shoes that make your legs look shorter: an ankle strap cuts your leg off, and platforms don’t create the leg-lengthening tippy-toe shape that traditional heels do. But clear heels are the holy grail of making your legs look like they go on for days. 

I’ve had these clear heels from Amazon for over two years and I take them out whenever I wear a cute minidress. They’re comfortable enough that you can dance in them at night, but I wouldn’t recommend wearing them for long walks since the repetitive motion can make the plastic cut into your feet. One mile was fine, but anything over that might be a little dicey. 

But for $40 Amazon shoes that I’ve had for years, they really do the trick. And don’t just take my word for it — these shoes have six thousand reviews on Amazon and nearly five stars, with people in the comments amazed at how comfortable they are. 

One look on the inside of these pumps and you’ll see why they’re so comfortable. Vivaia’s pressure relief insoles have padding exactly where you want it. Incredibly, there’s extra cushioning on the area between your heel and ankle where blisters usually appear so there’s no uncomfortable rubbing. The sole also has arch support, padding under the balls of your feet, and a shock-absorbent heel rebound. 

All of these bells and whistles combine to create a pump that you’ll want to wear all day. In fact, these actually feel like wearing sneakers! I’m never afraid of wearing these out of the house, no matter how far I’m going to be walking. Plus, the nude color makes these almost disappear so that you can pair them with anything. 

Just note that if you’re looking for the pressure relief insole, make sure you get the Melody Pro. The regular Melody is $20 less expensive and still has some features like the blister cushion, but it doesn’t have all the comfort features of the Pro.

This is our second pick from Cole Haan for the most comfortable heels and for good reason. These are the perfect casual mule for spring and summer. Like lots of the picks on this list, the sole is cushioned — which makes all the difference when it comes to comfort. The fun straps start at your toes and go all the way up your foot — so you won’t hear an annoying clop clop when you walk. Plus, the heel is the perfect Goldilocks height for lengthening your leg without being too high.

This comfortable heel is great for times when sneakers or Birkenstocks just won’t cut it, but you don’t want to have to pull out formal pumps or strappy stilettos. Pair them with jeans for brunch or wear them with a simple slip dress for rooftop happy hours. 

Plus, these are a great fit for feet that are atypical to slightly wide width. If you have feet that are significantly wider or narrower than normal, you might want to opt for a shoe with adjustable straps.

I got these shoes a few years ago and I keep coming back to them every time the weather is warm. Their original price is $109, but they’re always on sale for around $50-$60. And for that price, these are an amazing buy that won’t give you blisters or need time to break in.  In fact, they feel almost flat, so you won’t get any pain in the balls of your feet. 

I have them in the nude color and they’re a perfect neutral that will give you a little bit of height no matter what you’re wearing. And the outfits you can wear with these ultra-neutral shoes are endless. They’ll pair just as well with a pair of linen pants for brunch as they will with a maxi dress for a summer wedding. 

The only thing that I wish these shoes had is a slightly wider toe strap. The one on these shoes is a little bit narrow, which leaves something wanting when it comes to stability.

Another winner from a brand that we love. Here’s what I said about these stellar pumps in our Inez Review:

Pumps are difficult to get right. Unlike platforms or other kinds of creatively-designed shoes, there’s no way of getting around the steep pitch. In fact, these are particularly steep. Aptly called the Alta, they have a towering heel height of 3.5 inches. You can get the style in a lower-height heel, called the Lola, if this sounds a little too tall for you. But don’t be afraid to go with the higher heel. The shoes are far more comfortable than they look.

And while I probably wouldn’t recommend these for running around (you can literally run in some of Inez’s highest heels, like the Pilar below), they are the ultimate secret weapon for feeling authoritative and stylish at work. Paired with one of the best suits for women, the Alta pumps make the ultimate power outfit.

Margaux makes an amazing selection of carefully designed comfortable heels. This one is a slightly higher version of their ​​City Sandal — another winner when it comes to construction. But at a full three inches high, The Platform takes the cake for the best heel overall when it comes to combining height with walkability. 

There are lots of features that contribute to the comfort of this fabulous heel. First, it has five millimeters of cushioned padding on the sole that makes it feel like you’re putting on a slipper. Plus, the toe straps form Margaux ‘s signature “X” which adds stability that you wouldn’t get from a narrow, single strap. And finally, these shoes are handmade in Spain, meaning that there’s a ton of effort focused on the construction of the shoes that you won’t find in just any shoe made on an assembly line. 

Overall, I found these to be so walkable that I started using my pair as an everyday shoe — and not just the pair of cute heels that I only pull out for special occasions. In fact, I’m going to pack them for walking around and sightseeing when I’m in Italy, which is a huge testament to this heel’s top spot as the most comfortable heel.

Make sure you check out Margaux’s other shoes (like The Heel, a pump) for similarly stellar construction. We even reviewed Margaux’s Demi Flats and loved those too. 

Though I found it super comfortable on my typical-to-wide feet, some reviewers note that the heel area is a little wide for people with narrow feet. Also, there are reviewers who note that the ankle strap is a little bit loose. If that’s an issue for you with these (or any shoe), I suggest getting a leather hole puncher to add extra holes for the buckle. I have one and use it on everything from purses to belts and more!

Frankie4 is an Australian brand founded by podiatrists and focused on all-day comfort. The secret is their proprietary footbed that doesn’t just focus on arch support, but also cradles the ball of your foot. When you put on a Frankie4 shoe, you can definitely feel the difference a great footbed can make.

But these definitely don’t look like orthopedic shoes. The Juliett II is a beautiful sling that comes in tan and black. The pointed toe and open back are elegant without feeling too stuffy, so you can wear them to work and then to dinner. In fact, these would pair just as well with a great suit as they would with a flowy summer dress. 

And Frankie4 doesn’t just make comfortable heels. They also make sneakers and flats with the same proprietary footbed that I wish all my shoes had. 

I got a 7 in these shoes, which is my normal size, but they’re just a little too big. I would suggest going down a half size.

These suede, heeled boots are so comfy you could run in them. Here’s what I said about them in our best ankle boots review:

“Scarlett Chase’s motto is ‘shoes designed for wearing,’ and these are immensely wearable. They absolutely don’t look it — but they literally feel like sneakers. Inside, there’s a brilliantly designed arch support system that cradles your feet with padding.

“I’m a heel enthusiast and literally wrote the guide to the most comfortable heels by testing dozens upon dozens of shoes. In my professional opinion, these get a standing ovation. I’ve worn them for hours and hours with no pain, which is a huge feat for three-inch booties without a block heel or platform.”

In addition to testing the most comfortable heels, I’ve also tested dozens upon dozens of boots for our guide to the best ankle boots. Here’s what I said about this one: “What sets the Vivaia Regina Pro apart is not just the anti-slip outsole and pressure-relief herbal insole, but also the water-repellant upper that stretches to accommodate even the widest feet.

These boots are incredibly comfortable. The cloth material makes them super easy to slip on in the morning — plus, they’re kind of reminiscent of Balenciaga’s famous sock boots. But unlike Balenciaga boots, these are incredibly practical and sold at a great price point.”