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10 Stylish and Comfortable Boots for Older Women

By Sandra Roussy December 21, 2021 Makeup and Fashion

The colder months are fast approaching, and the time of year will come to slip out of our sandals and into our boots. Choosing boots is a very personal style choice, and it can change as we get older.

I used to love the high heeled boots when I was younger but now opt for more comfortable and stable footwear. But I still like my boots to look stylish.

We don’t need to sacrifice style, and we don’t need to shy away from trends because we are older women. A wider heel can be an option over stilettos, for example. A good balance of style and comfort is what to look for.

I have friends in their 50s and 60s who still look fabulous in high heeled boots and others who are still rocking Doc Martens. I think they all look great because they are confident about their personal styles.

Boots and booties look great with jeans, dresses, and skirts. Some are waterproof and excellent for snow activities and others are just cute to wear. I’ve picked a variety of styles of boots that I feel are stylish, comfortable, and easy to wear for older women. From the warm snow boots to the cute boots with heels.

Warm Snow Boots

The North Face Women’s Shellista III Mid Boots

The Shellista III is a perfect cold-weather, waterproof boot from The North Face for the adventurous women up north. They feature a removable insulated insole for extra comfort and stylish faux-fur trimming.

I had a pair very similar to these when I was living in Canada, and I didn’t need to use the laces, just slipped in and out very easily.

Columbia Ice Maiden™ II

Columbia Ice Maiden™ II

Columbia makes quality durable footwear. These waterproof woven boots made of synthetic textile upper and suede overlays provide support and protection.

Cute Ankle Booties

Esme Bootie Walking Cradles

Esme Bootie Walking Cradles

These soft leather booties have extra inside cushioning for all-day comfort. They are offered in regular and Wide widths. Booties look great with jeans and long skirts and dresses.

Clarks Addiy Terri

Clarks Addiy Terri

Booties are super trendy right now and these fashionable booties from Clark’s offer just the right combination of comfort and style.



Want a stylish bootie with a heel? This one from Sketchers offers a block heel that is comfortable and chic. One customer says, “Super comfy and super cute. I think I’ll be wearing these a lot! I’m glad I bought these boots.”

Calf-length Boots

Baretraps Willow Mid Shaft Women’s Boot

Baretraps Willow Mid Shaft Women's Boot

The fabric detail, buckle, and zipper give this calf-length boot just the right amount of style while staying classy. The block heel provides some extra height without compromising stability.

Wedged Bootie

Dr. Scholl’s Noelle

Dr. Scholl's Noelle

Wedges are a great way to get some height without losing stability – plus they are always trendy. These booties from Dr. Scholl’s provide an anatomical-cushioned footbed for all-day comfort and support.

Comfy Riding/Knee-Length Boots

Frye Melissa Button 2

Frye Melissa Button 2

These Frye boots are on the pricier side, but still very reasonable for a knee-length Italian leather riding boot. They come in an assortment of rich colors. Riding boots never go out of style and look great with jeans and knee-length skirts and dresses.

Sam Edelman Penny 2 Wide Calf Leather Riding Boot

Sam Edelman Penny 2 Wide Calf Leather Riding Boot

Do you need a wider boot? This riding boot from Sam Edelman offers a wider calf and a back zipper closure. Easy to put on and comfy to wear.

Koolaburra by UGG Madeley

Koolaburra by UGG Madeley

A thicker stacked heel will give you that extra height and these knee-length soft suede boots from UGG look stylish and are super comfortable.

Which boots are your favorite? Do you like to wear heels or keep to flat boots? Do you have any other suggestions for our community? Let’s have a conversation!

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The Author

Sandra is the middle-aged woman you hear about who sheds everything she owns and sets out into the world to rediscover and redefine herself. After more than twenty years spent in the fashion industry designing collections for brands such as La Senza, Victoria’s Secret, and JACOB Lingerie, she shifted her path and pursued her longtime passion for writing, traveling, and photography. Sandra was published in the NY Times best selling book Eat Pray Love Made Me Do It. A deeply personal essay hand-picked by Elizabeth Gilbert about loss, facing fears, and going after dreams. Visit her website: www.sandraroussy.com

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