The 9 Most Comfortable Boots for Women! (2021)



Most Comfortable Boots (2021)

Boots are probably my favorite type of shoe for women

This is completely ironic, of course, as freezing temperatures, blustery conditions, or both are the only reasons we even need boots in the first place! 

This simplicity – after all, boots are basically just a generic term for any shoe that provides high coverage and ideally some extra insulation as well – is exactly why I find boots such a versatile wardrobe element capable of making so many different fashion statements. 

Either that or this is the story I tell myself to get excited about getting dressed for weather so awful that even sitting pajama-clad on the couch and staring through the window makes me shiver and freeze.

If you’re looking to boot cold feet out of your winters, keep reading for the 9 most comfortable boots for women! 





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The Most Comfortable Boots

From the slopes to the sidewalk and the office to the outdoors, we have the most comfortable boots for women covered below! 


Most Comfortable Boots for Women







The Most Comfortable Boots for Women


Most Comfortable Shearling Boots: UGG


If you’ve ever been afraid to ask, shearling is freshly shorn sheepskin that is tanned, dyed, and processed with the original wool still attached. 

This material’s essential properties are superior durability, breathability, and naturally anti-microbial fibers. 

In plain English? 

Shearling is the most comfortable and longest-lasting fabric out there. Pair this with a brand like UGG, which crafts shoes so ridiculously and indisputably comfortable they are basically the cold weather version of Crocs, and you can at least count on your feet staying warm through winter! 

UGG Neumel

Sold on Zappos, UGG, Nordstrom, Backcountry, Journey's, Macy's & Amazon

Check the latest reviews and see all color options here





Most Comfortable Leather Boots: Everlane


The milder the weather, the less you need to worry about super high coverage or elaborately filled insulation. 

Aside from the obvious benefit of not freezing, these are the best boots days because they give you more freedom to make deliberate fashion statements. 

Every woman knows how few things are more powerful at making fashion statements or rounding out an outfit than pure, Italian black leather.

Add Everlane’s ridiculously fair pricing to the mix, and ask yourself why you’re still reading this instead of filling out your shipping address! 

Everlane The Boss Boot

Sold on Everlane

Check the latest reviews and see all color options here





Most Comfortable Winter Boots: J. Crew


Anyone who’s lived through New York winters or something similar (please consider relocating if God forbid your winters are worse) knows the point every season where it’s so cold that regular shoes make even a 5-minute walk excruciating. 

That’s why everyone enduring these types of winters needs a solid everyday winter boot.

I love having these adorable J. Crew boots as my go-to winter boot because they are extremely durable, break in very quickly, and work well with pretty much all everyday winter outfits!

The soles have solid traction and the insides are lined with cozy shearling. I went up half a size in order to wear thick wool socks, but otherwise they run true to size.

Best of all, they come with two pairs of colorful laces that you can swap them out for a different look!  

J. Crew Nordic Boots

Sold on J. Crew

Check the latest reviews and see all color options here





Most Comfortable Over the Knee Boots: Stuart Weitzman


While flannel-lined pants are kind of a thing for boys, the reality is women lack fashionable options that insulate the legs and lower body. 

Well…fashionable pants options, that is! 

Nothing makes a bold and confident fashion statement like a woman rocking some gorgeous and flashy over the knee boots, and few brands have perfected this boot niche quite like Stuart Weitzman

While these are definitely pricey, a pair of Stuart Weitzman over the knee boots will last you a lifetime.

The brand also makes these in every type of heel length, leather type and boot style, so you’re guaranteed to find the perfect pair of over the knee boots for your legs. Personally, I like the flat 5050 boots and the classic highlanders for a heeled option.

Wear these over skinny jeans, with a silky slip skirt or with a chunky ribbed sweater dress. These over the knee boots go with everything!

Stuart Weitzman The 5050 Boot

Sold on Zappos, Stuart Weitzman, Nordstrom, Bloomingdales, Shopbop, Revolve, Net A Porter & Amazon

Check the latest reviews and see all color options here





Most Comfortable Tall Boots: La Canadienne 


The images may be a little hard to tell, but these tall boots from La Canadienne are actually quite different from OTK (over-the-knee) boots in both size and purpose. 

Whereas OTK boots are meant to look distinct and be cleverly paired with a short dress or skirt, tall boots settle a few inches below your knee.

Knee length boots are truly meant as workhorse boots that can deflect heavy rain and splatter from winter’s worst, and no brand does it better than La Canadienne

The brand was founded in Montreal, Canada’s snowy and cold fashion capital. All of their boots are high quality leather and suede, super comfortable to wear all day long, and entirely waterproof for snowy icy conditions.

Featuring memory foam comfort on the insoles and your choice of completely waterproof leather or suede fabric on the upper, these La Canadienne boots actually make your feet forget what winter feels like!  

La Canadienne Passion

Sold on Zappos, Nordstrom & Amazon

Check the latest reviews and see all color options here





Most Comfortable Snow Boots: Sorel


Whether you work outside and need the most comfortable boots for standing all day or simply love hitting the slopes, check out these mid-height boots from revered footwear brand Sorel

Waterproof suede and an injection-molded waterproof rubber shell provide total protection from winter precipitation and sludge, while a faux-fur lining and removable EVA comfort footbed provide maximum (and guilt-free!) comfort. 

I wore these Sorel snow boots all throughout our Norway road trip and my feet stayed so cozy!

In Norway they don’t de-ice the roads, so the incredible traction on these boots saved my feet and allowed me to walk on sheets of slippery ice without a problem. Definitely one of the best snow boots around.

Sorel Snow Angel Lace

Sold on Zappos, Sorel, Nordstrom, Backcountry, Moosejaw, Net A Porter & Amazon

Check the latest reviews and see all color options here





Most Comfortable Work Boots: Blundstone


While people like me complain when 5-minute strolls turn into 15-minute marathons, some of you troopers out there work on your feet.

Like every day. What???

For those who need the most comfortable boots simply to function at work, check out the industrial-strength comfort features on these Blundstone work boots. 

The outsoles are simultaneously waterproof, lightweight, and designed for superior traction, the insoles and footbed feature enhanced cushioning and a patented shock-dispersing design, and the premium leather upper punctuates the Blundstone boot’s durability and professionalism! 

Blundstone BL558

Sold on Zappos, Madewell, Nordstrom & Amazon

Check the latest reviews and see all color options here





Most Comfortable Waterproof Boots: Blondo


Whenever people ask me about the difference between “water-resistant” and “waterproof” I always remind them that all “water-resistant” means is it takes you longer to get wet. 

Eventually, everything that’s “water-resistant” loses its impermeability and becomes just as soaked and awful as any other typical fabric (cotton, linen, fleece, etc.). 

Only waterproof fabrics are designed to remain dry regardless of the precipitation’s intensity or duration. Bottom line is always go for waterproof fabrics to be safe. 

This pair from Blondo is the most advanced waterproof boot I’ve been able to check out recently thanks to a unique seam-sealed construction that not only adds a second layer of defense against moisture, but also enhances the performance of an insulating textile inner lining! 

Blondo Villa Waterproof Bootie

Sold on Zappos, Nordstrom, Nordstrom Rack & Amazon

Check the latest reviews and see all color options here





Shop Comfortable Boots for Women





 Read More   in my favorite Comfy Shoe series:


Most Comfortable Shoes

The Most Comfortable Flats EVER

The Most Comfortable Sandals for Summer

The Most Comfortable Boots for Winter

The Most Comfortable Heels (you can actually walk in)


Best Sneakers

The Best White Sneakers that Go with EVERYTHING

Cute Casual Sneakers to Wear Anywhere

The Best Slip On Sneakers


Best Boots

The Best Chelsea Boots to Wear All Year Round

The Best Lace Up Boots for Military Inspired Chic

The Best Over the Knee Boots that Make a Statement!

The Best Shearling Boots to Stay Cozy this Winter

The Best Black Combat Boots That Go with Everything


Cozy At Home Shoes

Comfy Slippers for Women

Comfy Mens Slippers

The Best Mules for Easy Slip on Style

The Best Loafers to Look Polished but Stay Comfy


Shoe Reviews

The Best Travel Shoes in Every Style - Sneakers, Slip Ons, Flats & Sandals

Everlane Flats - These 5 Pairs are Extra Comfortable

OluKai Shoes: Sneaker & Sandal Review

Where to Get Stuart Weitzman Boots on Sale


Designer Inspired

The Best Cap Toe Ballet Flats to Get the Chanel Look, for Less

Classic Chanel Inspired Slingbacks (Two Toned)

The Best Chanel Inspired Espadrilles to Rock All Summer

The Best Manolo Blahnik Lookalikes

The Best Over the Knee Boots that Rival Stuart Weitzman Lowlands!


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