There are a few things I firmly believe someone can never have too much of, wardrobe-wise: well-fitting jeans, timeless white sneakers, and comfortable boots. But I know all too well that the latter can be a little harder to come by. I'd estimate that I've owned nearly 100 pairs of boots over the course of my lifetime so far, and not all of them were kind to my feet. These days, comfort is everything to me. Maybe I was willing to put up with aching arches or blistered heels just for the sake of looking cute in my 20s, but that's just not so anymore.
Knowing that fall was fast approaching, I recently made it my mission to find the most comfortable boots. And to determine the winners, I put every pair to the test by wearing them for a full 9-to-5 work day.
From waterproof lace-up boots and leather riding boots to chunky lug-sole Chelsea boots and suede heeled ankle booties, here are my favorite comfy pairs for every outfit and occasion.
For more of our rigorously-tested footwear coverage, see our articles on the most comfortable heels and the best walking shoes for women. And for boots specifically, check out the best knee-high boots and the best ankle boots.
Best overall: Everlane The Glove Boot
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.
Best budget: Athlefit Women’s Wedge Boots
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.
Best for a custom fit: DuoBoots Haltham
No other brand nails inclusive boot sizing quite like DuoBoots. The brand lets you customize both height — choosing from tall, standard, or petite — and width, with nine different calf sizes ranging from just under 12 inches to nearly 21.
Several of our editors, each with different calf shapes and sizes, tested the Haltham style and were unanimously impressed by the made-to-measure feel. It's rare to find one pair of boots that fits so many body types this well, but DuoBoots has managed to pull it off.
More reviews from the team
"As a tall plus-size lady, I've pretty much never been able to find an exact fit on knee-high boots. I can't stress how much of a game changer the custom calf sizing is. I really feel like I've found a super dialed-in fit that feels extremely comfortable."
In our DuoBoots review, she continues: "There's even room for me to go up a calf size if I eventually want to buy a pair to wear over jeans. That's a rarity in the plus-size world. Since getting my first set of DuoBoots over a year ago, I've occasionally considered other boot brands, but the lack of calf-sizing specificity from most brands (like, what does "extra wide calf" even mean?) turns me away. I'd much rather invest in a pair of custom-fit boots that I know will work for my body and, with some care, will last for years." — Lauren Savoie, our former deputy executive editor, who tested the Haltham in a tall fit and with an 18.5-inch shaft width
Most stylish: M.Gemi The Cristina
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.
Best knee-high boot: Naturalizer Rena 2 Riding Boot
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.
Best weather-resistant: Vivaia Tara Pro Water Repellent Wool Knee-High Boots
Vivaia's signature stretchy knit fabric makes their shoes both exceedingly comfortable and accommodating to all kinds of foot widths. Testers with wide feet, high-volume feet, and wider calves have all been fans of the elasticated construction. But they're not just easy to walk in — they're also highly practical.
More reviews from the team
"Vivaia's Tara Pros have been my go-to rain boots. I've worn them throughout the especially rainy stretch of weekends we've had in New York City, and falling raindrops would bead on the uppers and brush off with a simple swipe. I also tested them by pouring water over them before putting them on, and the flexible knit fabric wicks moisture so effectively that I was honestly impressed. You couldn't wear these as waders, but they're a more stylish alternative to rubber rain boots." — Gabrielle Chase, associate style editor, Insider Reviews.
Best for work: Madewell The Dimes Kitten-Heel Boot
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.
Best western-style: FRANKIE4 Shadow
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.
Best block heel: Inez Paz 70 Stretch
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.
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Disclosure: Written and researched by the Insider Reviews team. We highlight products and services you might find interesting. If you buy them, we may get a small share of the revenue from the sale from our partners. We may receive products free of charge from manufacturers to test. This does not drive our decision as to whether or not a product is featured or recommended. We operate independently from our advertising team. We welcome your feedback. Email us at reviews@bjinnox.com.
