The Best Comfortable Winter Boots for Older Ladies

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. But finding the best winter boots for older ladies can be difficult.

Just like I did with finding the most comfortable evening and dress shoes, I decided to put together a comprehensive guide of 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 that 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!

Best Winter Boots for Older Ladies

#1 Best Ankle Boot: Kork-Ease Renny Bootie

This ankle boot bodes a classic look paired with a hint of modern due to the side cut-outs and an exposed zipper closure on the back. With the cushioned footbed and arch support, you will be walking in comfort no matter where your day takes you. These would be my pick for the best winter boots for older ladies.

#2 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 2022-2023! This pair from Nisolo is crafted with memory foam, 5-layer insoles, and a waterproof leather upper to keep your feet comfortable and dry.

#3 Best Lug Sole Boot: Sam Edelman Laguna Waterproof Boot

Lug Sole Boots have a chunky heel, and these edgy shoes are certainly having a moment this season. I like that they add a little height without technically being a high heel, and the grippy sole means you are sure to keep great traction on wet, slippery days!

#4 Best Wedge Boot: Eileen Fisher Lilou Wedge

I love the chic and sporty twist this sawtooth 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.

#5 Best Waterproof Boot: Aquatalia Brigitte Luxe

This is a favorite brand by many that are known for their comfort. While the price is a little bit higher, you’ll have these for years to come, and they won’t go out of style. I love that they are water-resistant. I recommend sizing up!

#6 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. One reason why I chose these is that they have a stretchy back panel and are available in sizes 5-11.

#7 Best Snow Boot: Sorel Joan of Artic Faux Fur Snow Boot

For those of you that live (or are visiting) really cold climates, these faux fur waterproof snow boots should be in your closet. Read the reviews on them, and you’ll find out why. I was shocked to read they will keep your feet warm in weather all the way up to -25 degrees Fahrenheit!

#8 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 pair by Sam Edelman is also available in a medium brown (called Whiskey Leather) and Dark Brown.

#9 Best Cozy Boot: UGG Classic Mini II

UGG boots are a fan favorite in cold weather for a reason! Whether you’re running errands or simply getting the mail, you’ll want to slide these on. They offer the comfort of your favorite house shoe, plus a durable sole that provides traction. The minis are the most popular version right now.

#10 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.

#11 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 Boots for Wide Feet:

#12 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!

#13 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 current under $50 price make this pair a no-brainer to try.

Shop More of the Best Winter Boots for Older Ladies:

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.