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10 Stylish and Comfortable Boots for Older Women

By Sandra Roussy July 21, 2023 Beauty

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.

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Dr. Scholl’s Layla – Dr. Scholl’s Layla boots offer fashionable style and flexible comfort with a memory foam footbed, side zipper closure, and a sleek faux leather design. They are a practical and trendy choice for everyday wear.
  6. DREAM PAIRS Winter Boots – These mid-calf boots are stylish and durable with a synthetic leather upper and side zipper. These boots combine fashion and functionality, making them a versatile choice for winter wear.
  7. 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.
  8. Frye Melissa Button 2 – These 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.
  9. Sam Edelman Penny 2 Wide Calf Leather Riding Boot – This riding boot from Sam Edelman offers a wider calf and a back zipper closure. Easy to put on and comfy to wear.
  10. 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.

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 North Face Shellista III Mid is a versatile and stylish winter boot designed to keep your feet warm and protected in cold weather conditions. With a mid-cut height, it offers excellent coverage and support. 

The boot features a waterproof suede upper that helps repel moisture, while the insulated PrimaLoft insulation ensures superior warmth. The TNF Winter Grip rubber outsole provides excellent traction on various surfaces, keeping you stable and secure. The boot also includes a cozy faux fur collar for added comfort and a touch of elegance.

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

The Columbia Ice Maiden™ II is a reliable and durable winter boot that combines style and functionality. Designed to withstand cold and wet conditions, it features a waterproof leather and textile upper, keeping your feet dry and protected. 

The boot is insulated with 200g of insulation, providing exceptional warmth in freezing temperatures. Its Techlite™ lightweight midsole offers superior cushioning and support, while the non-marking rubber outsole ensures excellent traction on various surfaces. The faux fur collar adds a trendy touch, and the lace-up closure allows for a secure and customizable fit.

Cute Ankle Booties

Esme Bootie Walking Cradles

Esme Bootie Walking Cradles

The Esme Bootie by Walking Cradles is a stylish and comfortable choice if you are seeking a versatile and supportive bootie. Crafted with a premium leather upper, it showcases both durability and elegance. 

The bootie features a side zipper closure for easy on and off, while the cushioned footbed with Tiny Pillows® technology provides exceptional comfort and support. The flexible rubber outsole ensures reliable traction, making it suitable for all-day wear.

Clarks Addiy Terri

Clarks Addiy Terri

The Clarks Addiy Terri is a trendy ankle boot that effortlessly combines fashion and comfort. It is made with a premium leather upper for both durability and sophistication. The boot features a side zipper closure, allowing for easy on and off, while the cushioned OrthoLite® footbed provides superior comfort and support throughout the day. 

Its low-stacked heel offers a touch of elevation without sacrificing stability. The rubber outsole ensures reliable traction, making it suitable for various surfaces.

Calf-length Boots

Dr. Scholl’s Layla

Dr. Scholl’s Layla boots are a fashionable and comfortable option if you are seeking a flexible and supportive mid-calf boot. With a faux leather upper, these boots offer a stylish and durable design. 

The side zipper closure allows for easy on and off, while the cushioned insole provides exceptional comfort. The boots feature a memory foam Cool Fit™ footbed that contours to your feet for personalized support. The sturdy block heel adds a touch of height without sacrificing stability. 

DREAM PAIRS Winter Boots

The DREAM PAIRS  Mid-Calf Combat Riding Fashion Winter Boots are practical and trendy winter boots. They feature a synthetic leather upper and a side zipper that allows for easy on and off. The cushioned insole offers comfort and support, while the non-slip rubber outsole ensures reliable traction on various surfaces. With a mid-calf height and combat-inspired design, these boots effortlessly blend style and practicality, making them ideal for winter fashion and outdoor adventures.

Wedged Bootie

Dr. Scholl’s Noelle

Dr. Scholl's Noelle

Dr. Scholl’s Noelle is a sleek and comfortable ankle boot that offers both style and support. With a genuine leather or suede upper, these boots showcase durability and sophistication. The side zipper closure allows for easy on and off, while the cushioned insole provides superior comfort. 

The boots feature a memory foam Cool Fit™ footbed that molds to your feet for personalized cushioning. The wedge heel adds a touch of elevation without compromising stability. With their minimalist design and versatile appeal, Dr. Scholl’s Noelle boots are a reliable choice for all-day wear, effortlessly combining fashion and comfort.

Comfy Riding/Knee-Length Boots

Frye Melissa Button 2

Frye Melissa Button 2

The Frye boots, crafted from high-quality Italian leather, are a worthwhile investment despite their higher price point. With their knee-length design, they exude timeless elegance and come in a range of luxurious colors. 

Perfectly suited for both casual and dressy occasions, these riding boots effortlessly complement jeans, knee-length skirts, and dresses, ensuring a stylish and versatile look that transcends fashion trends.

Sam Edelman Penny 2 Wide Calf Leather Riding Boot

Sam Edelman Penny 2 Wide Calf Leather Riding Boot

The Sam Edelman Penny 2 Wide Calf Leather Riding Boot is a stunning and versatile choice for those with wider calves. Made from high-quality leather, these boots showcase durability and sophistication. 

With a wide calf design, they provide a comfortable and accommodating fit. The side zipper closure allows for easy on and off, while the cushioned insole ensures all-day comfort. The sleek and timeless riding boot style never goes out of fashion, effortlessly pairing with jeans, leggings, or dresses.

Koolaburra by UGG Madeley

Koolaburra by UGG Madeley

The Koolaburra by UGG Madeley is a stylish and cozy winter boot that offers a perfect blend of comfort and fashion. Made with a suede upper and genuine sheepskin lining, these boots provide warmth and luxury. 

The durable rubber outsole offers traction on various surfaces. With its mid-calf height and decorative buckle detail, the Madeley offers a trendy and versatile look that complements a wide range of outfits. Whether for casual or outdoor activities, these boots are a reliable choice for the colder months.

Let’s Have a Conversation:

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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Lisa Stege

Love the boots in the title photo, but don’t see them mentioned here.

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:

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