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7 Best Fall Boots for Women Over 50

By Sandra Roussy November 08, 2023 Makeup and Fashion

As the leaves continue to paint the world in shades of crimson and amber, there’s an undeniable sense of magic in the air, signaling the arrival of fall. This season represents a unique opportunity to embrace both style and comfort, and nothing complements the crisp autumn breeze quite like a perfect pair of boots.

  1. Journee Collection Sanora Wide Calf Stacked Heel Riding Boots – These boots, available at Target, offer a comfortable fit for wider calves and a classic faux leather design with a stacked heel for versatility. With a side zipper for easy wear, they are a stylish and practical choice for fall.
  2. Madewell The Drumgold Boot in Extended Calf – These Madewell boots blend style and inclusivity with premium leather and an extended calf width for a comfortable fit. These mid-calf boots feature a side zipper and a sturdy stacked heel, making them easy to wear and fashionable for various occasions.
  3. Blowfish Malibu Vanitee – These boots blend fashion and function with a synthetic polyurethane upper, sustainable insole, and buckle straps. They provide style, comfort, and durability for outdoor adventures and also casual outings.
  4. Allair Over The Knee Boots from Nine West – These Nine West boots combine sophistication and practicality with their modern design and comfortable low heel. They are perfect for making a fashionable statement while maintaining comfort and stability.
  5. Vaneli Pensee – These boots offer chic comfort with a leather upper, faux leather insole, and trendy block heel. These ankle-high boots, featuring a squared toe and zipper closure, are super stylish.
  6. UGG Classic Cardi Cabled Knit – These UGG knit boots combine luxury and warmth with a classic cable-knit pattern, soft suede upper, and sheepskin lining. These boots offer both fashion and comfort for the colder months, making them an ideal choice for winter wardrobes.
  7. katliu Slouchy Mid Calf Boots – These budget friendly boots offer a trendy and comfortable option with their slouchy design and flat sole. They are easy to wear with a convenient side zipper and can effortlessly enhance your casual or evening outfit.

Whether you’re savoring a leisurely stroll through vibrant foliage, attending social gatherings, or simply relishing the cozy ambiance of your neighborhood, the right pair of boots can be your trusty companion.

Let’s check the latest trends, timeless classics, and invaluable tips to help you select the ideal boots that not only show your style but also provide the support and comfort your lifestyle demands.

How to Choose Your Perfect Pair of Fall Boots

Choosing the perfect fall boots involves considering various factors to ensure they suit your style, needs, and the autumn weather.

Determine Your Style Preferences

Consider your personal style. Do you prefer classic, casual, edgy, or trendy looks? Knowing your style will help narrow down your options.

Selecting Boot Length

Decide on the boot length that suits your style and practicality. Options include ankle boots, mid-calf boots, knee-high boots, and over-the-knee boots.

Choose Materials Wisely

Pay attention to the material of the boots. Leather is durable and can be waterproofed, while suede adds a touch of luxury but needs more care. Synthetic materials are often more affordable and provide the best waterproof features.

Comfort and Fit Are Key

Comfort is paramount. Ensure the boots fit well, allowing ample room for your toes while fitting snugly around the ankles. Many brands and styles now offer wide-calf options. Look for boots with cushioned insoles and arch support if needed.

Heel Height

Lower heels are more comfortable for everyday wear, while higher heels can add a touch of elegance but may not be as sensible for extended periods of walking.

Weather-Appropriate Features

For fall weather, boots with good traction on the soles are essential to prevent slipping on wet leaves or sidewalks. Waterproof or water-resistant options are also great for wet conditions.

Color and Versatility

If you want your boots to last several seasons choose timeless colors like brown, black, or neutral shades that can easily be paired with various outfits. However, don’t shy away from experimenting with bold colors or trendy patterns if they suit your style. But remember, they may feel outdated sooner than the more conventional colors.

Consider Your Wardrobe

Think about how your new boots will integrate into your existing wardrobe. Do they match your fall clothing items, such as jeans, skirts, or dresses?

Try Before You Buy

Always try boots on before purchasing, preferably at the end of the day when your feet are slightly swollen. Walk around to assess comfort and fit.

Brand and Reviews

Research brands that are known for their quality and comfort. Read online reviews and ask for recommendations from friends or family members.


Consider the maintenance required for the boots. Leather may need conditioning, suede should be protected, and regular cleaning can prolong the life of any material.

Return Policy

Be aware of the store’s return policy in case the boots don’t meet your expectations or if they don’t fit comfortably.

Remember that the perfect fall boots for you should not only enhance your style but also offer the comfort and practicality required for your lifestyle during the autumn season. Take your time to choose wisely, and you’ll enjoy both fashion and function throughout the fall.

Fall Boots for Women Over 50

Journee Collection Sanora Wide Calf Stacked Heel Riding Boots

Journee Collection Sanora Wide Calf Stacked Heel Riding Boots

The Journee Collection Sanora Wide Calf Stacked Heel Riding Boots, available at Target, are a versatile and contemporary addition to any fall wardrobe. These boots are designed to cater to those with wider calves, ensuring a comfortable fit without compromising on fashion.

Crafted with high-quality faux leather, the Sanora boots offer a sleek and polished appearance, reminiscent of classic riding boots. The stacked heel provides an elegant lift while maintaining stability, making them suitable for various occasions. With their timeless look, they effortlessly pair with both jeans and dresses.

These riding boots feature a convenient side zipper for easy on-and-off wear. Whether you’re strolling through autumn leaves or stepping out for a casual gathering, the Journee Collection Sanora boots combine style, comfort, and affordability for a fantastic fall footwear choice.

Madewell The Drumgold Boot in Extended Calf

Madewell The Drumgold Boot in Extended Calf

Madewell’s The Drumgold Boot in Extended Calf is a great combination of style and comfort. These boots are designed to accommodate wider calves, offering a comfy and flattering fit for a broader range of body types.

Crafted with premium leather, This boot exudes a rustic, timeless charm that pairs effortlessly with various outfits. Its height strikes the perfect balance between casual and chic, making it suitable for everyday wear or dressing up for special occasions.

These boots feature a side zipper for easy on-and-off access, saving you time and effort. The extended calf width ensures a comfortable fit without sacrificing style. The sturdy stacked heel provides stability and a touch of elevation, adding to their overall versatility.

Blowfish Malibu Vanitee

Blowfish Malibu Vanitee

Step into the great outdoors with confidence and style by slipping into the cozy comfort of Blowfish Malibu® Vanitee boots. These boots are designed to not only keep your feet warm and snug but also showcase a blend of functionality and fashion.

The Vanitee boots boast a synthetic polyurethane upper, ensuring durability and resistance to the elements while exuding a casual chic aesthetic. Inside, you’ll find an insole made with BLOOM foam, a sustainable material derived from algae, promoting both comfort and eco-consciousness.

A useful inside zipper allows for easy on-and-off wear. Adding a touch of style, the boots feature buckle straps on the shaft and ankle, creating a fashionable accent. The round-toe design provides ample space for your toes, ensuring comfort during long walks or outings.

A small stacked heel offers stability and a slight elevation. The synthetic midsole and outsole provide durability and traction, making these boots suitable for various outdoor activities.

Whether you’re exploring nature trails or simply strolling through the city streets, Blowfish Malibu® Vanitee boots offer the perfect combination of comfort, style, and functionality.

Allair Over The Knee Boots from Nine West

Allair Over The Knee Boots from Nine West

The “Allair Over The Knee Boots” by Nine West are the epitome of sophistication and style, offering a captivating blend of fashion-forward design and practicality. These boots are meticulously crafted to make a bold fashion statement while providing comfort for long-lasting wear.

With a versatile over-the-knee design, the Allair boots elongate the legs and exude a sense of confidence and elegance. The high-quality suede upper materials not only look luxurious but also ensure durability.

These boots feature a convenient zipper closure on the inside, making them easy to slip on and off. The pointed-toe design adds a chic and sleek finish to any outfit, whether you’re dressing up for a night out or adding flair to your everyday outfit.

Vaneli Pensee

Vaneli Pensee

Boost your style effortlessly while prioritizing comfort with Vaneli® Pensee Boots. These cute ankle-high boots are a perfect combination of fashion and functionality, making them an ideal choice for those who appreciate both style and comfort.

Crafted with a supple suede upper, these boots exude a sense of luxury while ensuring durability. The synthetic lining adds to the overall comfort and durability of the boots, making them suitable for extended wear. Inside, a faux leather insole provides cushioning for your feet, allowing you to stay comfortable throughout the day.

The squared toe shape adds a contemporary touch to the design, and the zipper closure on the side ensures easy on-and-off wear. With a unique shaped block heel, these boots offer both stability and that trendy touch making them perfect for various occasions. The rubber outsole provides excellent traction and durability, ensuring these boots are suitable for different terrains and weather conditions.

UGG Classic Cardi Cabled Knit

UGG Classic Cardi Cabled Knit

The UGG Classic Cardi Cabled Knit is a luxurious and cozy addition to any casual fall outfit. Designed to keep you warm and stylish during the colder months, these boots feature a unique cable-knit pattern, reminiscent of your favorite chunky sweater, adding a touch of texture and sophistication to your fall/winter wardrobe.

Crafted from premium materials, including a soft suede upper and a plush sheepskin lining, these boots offer unparalleled warmth and comfort. The sheepskin insole naturally wicks away moisture, keeping your feet dry and cozy, while the Treadlite by UGG™ outsole provides excellent traction and durability.

With a classic UGG silhouette, including a rounded toe and a medium-height shaft, these boots are easy to slip on and off, making them perfect for everyday wear. The wooden button and elastic closure on the side add a modern and functional touch to the design.

katliu Slouchy Mid-Calf Boots

katliu Slouchy Mid-Calf Boots

The katliu Women’s Slouchy Mid-Calf Boots are a fashionable and budget friendly choice for those seeking a relaxed yet stylish look. These boots are designed with a slouchy mid-calf height, offering a casual and trendy appearance that’s perfect for various occasions.

The slouchy style adds a touch of personality to your outfit, and the mid-calf height keeps you comfortable and cozy without overheating. The zipper closure along the inside ensures easy on-and-off wear, while the flat sole adds comfort for extended use.

Katliu Women’s Slouchy Mid-Calf Boots are an excellent choice for those who value style and comfort equally. Whether you’re stepping out for a casual day or adding a trendy twist to your evening look, these boots are a great addition to your footwear collection.



Let’s Have a Conversation:

Are you in the market for a new pair of fall boots? Which ones on our list are your favorites? Tell us about it in the comments below.

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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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