The Best Comfortable Winter Boots for Women Over 50

Boot season is one of my favorites! I find boots and booties to be one of the comfiest footwear options to wear in the winter. They’re stable around your ankle, providing more support than a shoe, and they also keep your feet warm and dry during nasty weather. Finding the best winter boots can be tricky as you get older because our feet demand comfort.

Just like I did with finding the most comfortable evening and dress shoes, I decided to put together a comprehensive guide to the most comfortable boots for women. I made sure to pull a variety of options that fit all budgets and style preferences, even for those of you who have a wide calf or need wider widths. Whether you’re shopping for the perfect ankle boot, knee-high boot, or snow boot, this guide offers a full list so you can make the best selection for you! If you don’t know the best way to style boots, I’ve covered that here and here.

P.S. If you struggle with finding comfortable shoes, you may enjoy this post: How to Make Your Shoes More Comfortable. You might also enjoy reading these: Best, Most Comfortable House Slippers for Women, The Best Slip-on Shoes for Women Over 50, and Best Sneakers and Walking Shoes for Mature Feet.

Best Winter Boots for Women Over 50

Best Ankle Boot: LifeStride Aurora

These Lifestride ankle booties are super comfy with a memory foam insole and a stable 1 3/8″ heel that feels virtually flat. They also have a gore inset that stretches when you walk. I bought the black microsuede, and they come in five other colors. They come in sizes 5-12, medium and wide widths.

Best Flat Lace-up Boot: Munro Finnley

These Finnley Lace Up boots from Munro get worn more than any of my other footwear during the winter, and I’d struggle without them. I love them so much that after 5 years with the black, I invested in a taupe pair. They’re water-resistant, so perfect for damp weather and very comfortable.

Best Kitten Heel Sock Bootie: Eileen Fisher Purl

I’ve needed a sock bootie in my wardrobe for several years but needed a very low heel so I was thrilled to find these ones by Eileen Fisher. She makes a lot of knit booties which I find extremely forgiving on my bunion.

Sock booties with a higher tight shaft are perfect to wear with a narrower leg because they’ll stay put and not interfere with the pants. They also work well with color-coordinated tights and skirts to give a continuous line that helps your legs look longer. I went up a half size in these because my feet are square and the toe is slightly pointed.

Best Chelsea Boot: Nisolo Everyday Chelsea Boot

Did you know Chelsea boots originated in the days of Queen Victoria? This classic style boot has transcended time and is now one of the it-shoes of 2023-2024! This pair from Nisolo is crafted with memory foam, 5-layer insoles, and a waterproof leather upper to keep your feet comfortable and dry. It comes in four classic colors and has a ton of great reviews.

Best Knit Bootie: Eileen Fisher Clever Block Heel

Here’s another pair of Eileen Fisher knit booties that I have worn, and worn. Their low, block heel is super easy on my feet and back, so I can comfortably wear them all day. I have gray which is an especially useful color in my wardrobe. They also come in black.

Best Lug Sole Boot: Easy Spirit Morgan

Lug Sole boots have a a nice chunky heel and have extra cushioning so they’re very comfy. They also have a grippy sole which gives you great traction on wet, slippery days! Lug sole booties look great with wide-leg pants and jeans because the wider leg adds visual weight, which helps balance the boot. They also look great with leggings tucked into them and a long, cozy sweater. I’ve worn these navy Easy Spirit booties a ton this year because they are so comfortable.

Best Wedge Boot: Eileen Fisher Chelsea Wedge

I love the chic and sporty twist the wedge brings to this bootie. I think they would look great dressed up or down. I’ve got several pairs of Eileen Fisher boots and find them very comfortable.

Best Waterproof Boot: Blondo Dakota Bootie

Winter often comes with a lot of gloomy, wet weather. A nice pair of waterproof or water resistant boots can be important if you spend a lot of time outdoors or walking from place to place. I love that these Blondo boots have a higher shaft so you don’t have to worry about water splashing onto your ankles. My Munro boots above are also water resistant, so they make another great option.

Best Knee High Boot: Teva Anaya Tall Boot

Knee High boots look great with so many outfits! I love pairing them with dresses, skinny jeans, or a tunic length top and leggings. I love that these Teva boots have a stretchy side panel for calf hugging comfort. They’re also waterproof and are available in sizes 5-11.

Best Snow Boot: Sorel Joan of Artic with Faux Fur

For those of you that live (or are visiting) really cold climates, these Sorel faux fur waterproof snow boots should be in your closet. They have amazing reviews from happy customers and they’ll keep your feet warm in weather all the way down to -25 degrees Fahrenheit!

Best Riding Boot: Sam Edelman Penny Leather Riding Boot

Riding boots are some of my very favorite boots for mastering a sleek and sophisticated silhouette in the winter months! This Sam Edelman Penny Leather riding boot is classic with an almond toe and equastrian vibes. I love to tuck my slim pants into riding boots an wear with an oversized sweater.

Best Cozy Boot: UGG Classic Mini II

UGG boots are a fan favorite in cold weather for a reason…warmth and comfort! These minis are the most popular version right now. Quince’s Australian Shearling boots might be a great alternative if you aren’t looking to splurge currently. They get great reviews and they are much friendlier on the wallet.

Best Wide Calf Boot: LifeStride X-Anita Boot

I’ve heard just how hard it can be to find a wide calf boot. The stretch knit panel crafted into these beautiful LifeStride boots provides a flexible fit making them ideal for women with wider calves.

Best Boot for Small Feet: Teva Anaya Bootie

Another pair of Tevas made the list, and these adorable little zippered booties are great for those of you with size 5 feet.

Best Winter Boots for Wide Feet:

Dr. Scholl’s Rate Ankle Boot

This little black bootie is anything but basic. I love the geometric detailing. Plus, you know if it’s from Dr. Scholl’s that it’s going to be so comfortable!

Skechers On The Go Chukka Boot

I know lots of you love Skechers and a good deal, and this Chukka Boot by Skechers is it. The faux fur detail and under $50 price, make this great pair to try.

More Winter Boots for Women Over 50:

Are boots and booties part of your fall/winter wardrobe? What are some of your favorites?

Thanks for reading, and be sure to wear what makes you feel confident.