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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.

EASY SPIRIT MORGAN LUG SOLE BOOTIE

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

WEARING – ANKLE BOOTIES / TALBOTS JEANS / QUINCE CASHMERE TEE size M / LONG SWEATER BLAZER size XXS / QUINCE ITALIAN LEATHER HANDBAG / CABLE HOOP EARRINGS

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

WEARING – MUNRO BOOTIE / ATHLETA CASHMERE BLEND SWEATER size S / PISTOLA JEANS size 29 / QUINCE ITALIAN LEATHER HANDBAG

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.

WEARING / EF SOCK BOOTIES / ATHLETA SWEATER size S / MOTHER JEANS size 29 / GUCCI SHOULDER BAG (RESALE HERE) / LAGOS NECKLACE / JENNY BIRD EARRINGS

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

WEARING : LUG SOLE BOOTIE / SIMILAR SWEATER size M / LEVI’S JEANS size 29 SHORT/ JENNY BIRD PUFFY FAYE EARINGS / BEIGE TOTE

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.

18 Comments

  1. I find that lately I’ve just been wearing ankle boots. I love my Ugg wedge boots but we’ve hardly had any snow this year so mostly just wearing tennis shoes.

  2. I now have two pair of Skechers booties. Santa gave me a pair of black suede with grey fur around the top and little side zippers. They are so comfortable! I also have similar in pale grey. I wear 7W so my styles and color choices are limited. But these both feel like warm slippers on my painful feel. Skechers are the one brand that really helps relieve pain in my feet.

  3. I LOVE ankle boots! I haven’t worn thigh high boots for a couple of years now. My favorites are several different styles by Dansko and a recent purchase from Josef Sebel that are fleece lined. I find ankle boots so comfortable and stable I wish I could wear them all year!

    1. I really love them too

  4. Cheryl Akridge says:

    What do you think of the Brighton booties? I have been looking at a couple of theirs but unsure if they will stay in style for long?

  5. Great post as usual! I bought the Easy Spirit Morgan Lug Sole Bootie in navy when you recently reviewed them and I love them! Based on your reviews working so well for me, I just ordered the Munro Finley Lace Up and the Sketchers On the Go Chukka boot! Years ago in my 20″s with 5 young children, my sister in law once asked me if I only had one pair of shoes! That was about right. Now, sadly for our budget (?!), shoes are a weakness for me! You’re not helping! Sounds like you had a wonderful Christmas and I hope you enjoy the New Year with your new sweet grandchild and vacation home in BC!

    1. Happy New Year Deby! I just ordered a new pair of sketchers for walking because my feet are screaming for more cushioning.

  6. Thank you for the boot low down!
    Now, could you please find some sweaters with natural fibers especially wool for those of us who live in cold and get cold in winter? Other than the Quince thin cashmere, which I love, I haven’t been able to find a warm sweater to buy in years. Thanks

    1. I think the new low ones look great

  7. Ankle boots are essential for winter. I add felt insoles to mine. I have narrow feet in a half size. Many winter boots are sold only in full sizes, so I have to size up, which leaves extra room for my insoles. I still higher felt-pac winter boots like the ones you’ve shown, for the coldest days and deep snow. I carry them in my vehicle all winter long, in case I get stuck. Thank you for this.

    1. That’s so smart to carry them in your car!

  8. Jennifer, thanks for all the choices. I’m on my way to Nordstrom’s today to check out their boot sale. Hoping to pick up a few pair, tall and ankle…Happy New Year.
    ps. I have pair of Aquatalia ankle waterproof booties, I love them..

  9. Lots of lovely, comfortable choices. Thank you for these insights!

  10. Carol Morley says:

    Jennifer, through the years my favorite winter boots have been the Aquatalia water resistant boots. While an investment, my bootie and riding boot have kept my feet dry and warm for many years. I have others, but these are my go to. Thank you for all the ideas and expertise you’ve provided during 2023! Wishing you a 2024 full of health, joy, hope and hugs! 🥂

    1. I invested in one pair of Aquatalia boots and treasure them. Such a gorgeously made boot! Happy New Year Carol

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