The Most Comfortable Boots For Women, According To Rigorous Testing

Rebecca Strong

After trying out this beauty from Everlane, I am officially a sock boot convert. Here's why.

The fit is flawless. As the name of these ankle boots suggests, the Everlane Glove Boots really do fit like a glove because the upper is made with a stretchy ribbed knit fabric. Even when a pair of boots that fit my feet, I often find that the shaft is either too big or too tight — but that's not an issue here since they stretch and mold to my ankles and calves.

The versatility is unmatched. The sensible 2-inch heel is manageable for all-day wear but also just high enough that I can dress these boots up for after-work dinner or drinks.

More reviews from the team

"The heel is just high enough to make the shoe feel polished but not so high that it hurts my arches or ankles. In fact, they just feel like walking in ultra-comfy flat boots." — Sally Kaplan, executive editor.

"It's easy to slip into, slide out of, and molds to your feet in all the right places. The two-inch heel is the perfect height for everyday activities, plus it's chunky enough to walk in comfortably even if you hate walking in any footwear besides a sneaker." — Remi Rosmarin, freelance style writer.

Read our full Everlane Glove Boot review.

Rebecca Strong

They're comfy from first wear. Some boots take me days, or even weeks, to break in. Not The M.Gemi Cristina — from the first time I donned them, they fit like a dream, thanks in part to the buttery nappa leather that doesn't feel the slightest stiff or restrictive. The rubber sole inserts offer some traction on slippery surfaces, and since the toebox is a bit wider, my toes never feel squished.

They feature the "Goldilocks" of heel heights. I live for a sturdy block heel, and with The Cristina boot, M. Gemi managed to find that "just-right" height at 2.2 inches, which can lean either casual or dressy and is reasonable to wear all-day long.

There are so many colors to choose from. The Christina comes in seven color options, and while there are no shortage of classic neutrals to choose from, I'm obsessed with the metallic gunmetal. It instantly adds some personality to an otherwise basic ensemble like a white sweater and jeans, or a little black dress.

More reviews from the team

"If M.Gemi is known for one thing, it's craftsmanship — and these booties are no exception. Not only is The Christina crafted with luxe materials like Italian calf hair and Nappa leather, but they're also handmade at artisan workshops in Tuscany. And the quality of materials and construction shows. These booties fit like a glove right out of the box, with no need to break them in." —Samantha Crozier, style editor.

Read our full M.Gemi review.

Rebecca Strong

They look surprisingly high-quality. Buying budget-friendly footwear on Amazon really is a crapshoot — sometimes what I get looks hilariously nothing like what I ordered. But every once in a while I get lucky, like I did with this pair of platform wedge booties from Athlefit. Even though they're made with faux suede, they look like they could easily cost twice what I paid for them.

The features are ultra-practical. The elastic side bands and heel loop make them super easy to slip on and off, and the thick non-slip lug sole gives me some added peace of mind on slippery days (I'm clumsy, OK?).

I can dress them up or down. These booties are fairly versatile, too: I can style them with sweater dresses, jeans, ang leggings alike.

Rebecca Strong

They're super flattering. Magic — there's literally no other explanation for how these booties make my ultra-wide feet look so slim. Somehow, the "snip" toe offers ample room while still providing a tapered look that visually elongates my legs.

The fit feels customized. The Inez Paz 70 is absurdly comfortable. I'll chalk that up to the proprietary plush insole, which offers plenty of cushioning and arch support — and the fact that the luxe suede upper has plenty of stretch to hug my foot like it was custom made.

They're impossibly chic. Also worth mentioning? Whether I'm wearing these with straight-leg jeans, ponte leggings, and pencil skirts, I can safely assume I'll get some compliments.

More reviews from the team

"What can I say about these except that they're another hit by one of my favorite brands ever for comfortable, stylish shoes? I've reviewed Inez and raved about almost all their footwear. This one is no exception.

"It is made of soft, flexible leather. The footbed is secure and soft. Plus, it is exceedingly walkable — even when you don't account for the fact that the heel is over three inches high." —Samantha Crozier, style editor, who tested the higher-heeled Paz 90.

Read our full Inez review.

Rebecca Strong

They'll never go out of style. The Dimes boot by Madewell is the little black dress of boots, as far as I'm concerned. Sleek, chic, and super versatile, I can't really think of an occasion where these wouldn't be appropriate. And they come in 7 stunning color options, ranging from a rich merlot leather to warm tawny suede.

There's lots of supportive cushioning. What makes these boots so comfortable is that they feature the brand's signature Cloudlift Lite padding. The cushioned midsoles truly do make it feel like I'm walking on a cloud, hugging my arches in all the rich places — and the squared-off almond shape toe is oh-so-flattering on my feet.

They're an ethical purchase. As an added perk, I love that these boots are constructed with leather sourced from the Leather Working Group — which works with tanneries using sustainable practices.

Rebecca Strong/Insider

They're made to last. Sorel has quite a reputation for making high-quality, durable boots that can withstand all weather conditions and the Ona Ave is no exception. And despite how sturdy they are — with a rubber outsole that provides plenty of grip — they're also surprisingly lightweight. The side zippers and pull tabs are a nice touch, too, making them a cinch to get on when I'm rushing out the door.

They're suitable for all weather. Thanks to the waterproof full-grain leather upper, I don't have to stress if there's some unexpected rain or even snow while I'm wearing these.

They have a casual yet versatile look. The lace-up style makes these kind of look like a sneaker boot, and I don't hate it — it's a laid-back look that works equally well with a concert tee and leather leggings as it does with a bodysuit and denim skirt.

The only drawback to these is that they do seem to scuff fairly easily, but I find that my trusty Magic Eraser can instantly wipe those marks away.

Rebecca Strong/Insider Reviews

Chelsea boots are a must-have in every shoe collection, IMO — this thick-soled, elastic-sided style will always be "in." They can toughen up a feminine skirt or dress, lend a chill vibe to suiting, and carry you from fall all the way through spring. As soon as I slipped on the Timberland Everleigh, I knew this was going to become one of my go-to pairs of boots.

The toebox is roomy. My feet are pretty wide, and these boots accommodate them perfectly with no pinching or squeezing.

The support is unmatched. The OrthoLite® Impressions footbed truly acts as cushy memory foam mattress that molds to my feet, and due to the chunky platform the 3-inch heel height feels closer to 1-inch. I literally feel like I'm walking on clouds when I have these on.

They slip on with ease. Slip-on boots can be dicey — I've definitely wrestled to get them on in the past — but these were a breeze to put on and take off. That's because of the wide stretchy gore on both sides of the shaft.

Unfortunately, these boots aren't waterproof — but I plan to spray them with a weatherproofing spray so I can wear them on rainy and snowy days without fear of wrecking them.

Rebecca Strong/Insider

They're designed by an expert. What sets FRANKIE4 shoes apart is that the brand was founded by a podiatrist — so, needless to say, the products are designed with comfort and practicality in mind. Fortunately, their footwear is just as stylish as it is sensible.

They're right on trend. I've been on a tireless hunt for the perfect little Western-inspired bootie, and I finally found it. The FRANKIE4 Shadow pairs equally well with mom jeans as it does with miniskirts.

My feet are thrilled. Often I need to rotate my boots to avoid aches and blisters, but I can wear these for days on end without the slightest issue. That's due to the triple-layered system that cushions my soles, supports my arches, and ensures better alignment. Another huge bonus is that the FRANKIE4 comes with extra footbed inserts so that I'm able to get a perfectly personalized fit.

Rebecca Strong/Insider

While I've flirted with many boot styles in my lifetime, the kitten heel remains my one true love. I look less graceful than a T-rex when walking in sky-high heels — a kitten heel is the perfect compromise because it's way easier for me to walk in but still gives me a little lift. And if there's one thing I've learned while shopping recently, it's not to sleep on the J.Crew shoe collection — especially the Stevie boot.

My feet aren't cranky after wearing them. Since the angle created by kitten heels puts less pressure on the ball of my foot, I find that I'm far less likely to deal with any pain after a long day of wearing them.

They're an updated fan favorite. The Stevie has consistently remained a customer favorite, and the company recently redesigned the shoe with some thoughtful tweaks — including a convenient pull-on fit, a welt for a more high-quality feel, and a more refined heel.

They're suitable for so many situations. The 2.24-inch heel on these knee-high boots is reasonable enough that I be on my feet for long hours at, say, a networking event or cocktail party. And I love that I can pop them on with a blazer dress, or a cowl-neck sweater dress, and transition seamlessly from a work meeting to date night.

The one thing I will say about the Stevie is that the back part that cradles your heel can feel a bit stiff when you first put them on — but rest assured that this will soften and stretch with wear.

Rebecca Strong/Insider

Quick footwear history lesson: When Naturalizer launched in the 1920s, it was the first shoe brand designed specifically for women. Throughout the years, the brand has always prioritizied comfort and ergonomics without sacrificing style. Case in point: The Naturalizer Rena 2 Riding Boot is both trendy and timeless, both chic and comfortable.

It's all in the details. Riding boots are a classic for a reason: they work with everything from floaty floral dresses to distressed boot-leg jeans. But the features that make the Naturalizer Rena 2 stand out are the eye-catching criss-cross straps, flattering almond-shaped toe, and polished buckles. The fact that they zip on and off is a plus for me, too, because pull-on styles don't tend to be as svelte in the ankle area.

They're made with the environment in mind. I also appreciate that the leather used to make these boots is sustainable sourced form Leather Working Group certified tanneries, and the lining is made from 100% recycled materials.

They're exceptionally comfortable. Most importantly, though, thanks to the 1-inch block heel, removable insole, and Contour+ Comfort technology, I definitely wasn't racing to tear these off at the end of my work day.