13 Best Boots for Women Over 50, Tested: Knee-Highs, Cowboy Boots, More Comfortable Options
Alexa, play “These Boots Are Made For Walkin’” by Nancy Sinatra
We’ve been waiting, and it’s finally here: Boot season has officially arrived. While we’re all for the pumpkin spice lattes, plaid patterns and cozy shackets fall brings with it, the chance to kick out our favorite boots (no pun intended) we stored away all summer has us bursting with excitement for the season. Truly, it’s hard to think of a more versatile shoe option for fall and winter than boots—they can easily be dressed up with skirts and dresses or down with jeans, pants and even sweats (hello, slipper boots). And with so many different styles to choose from, from pointed toes to cowboy boots to chic booties, you’re sure to find the best pair for you. But there’s more to picking the best boots than meets the eye. Comfort is and should be a huge factor—especially if you’re a woman over 50. That’s why we rounded up the best boots for women, including the best cowboy boots too, that were made with both comfort and style in mind. Keep reading for arch support options, wide calf picks and more.
What to look for in boots for women over 50
If you’re on the hunt for a new pair of boots this season, there are a few key things you should keep in mind. As we get older, our feet age with us—especially for women. Women are more likely to suffer from chronic foot issues than men, due to many years spent wearing unsupportive shoes like poor quality high heels, fluctuations in weight, pregnancy and a plethora of other reasons. And as we age, our feet tend to “flatten,” meaning they start to lose their natural arch and cushioning, requiring extra support.
That’s why it’s so important to look for boots that are supportive and comfortable. Below, a few key features to look for in the best boots for women:
Boots with arch support
As mentioned above, it’s common for our feet to “flatten” the older we get and the more stress we’ve put on them. Therefore, looking for boots that have arch support is a huge plus in our book to help give our feet back that arch they’re lacking.
Boots with added cushioning
Next, look for boots with comfortable, supportive cushioning—especially if you prefer heeled boots or booties. With a heel, we’re typically going to feel more weight on the balls and heels of our feet than we would with flats, so choosing a pair of boots with adequate cushioning is key. Cushioning is important regardless, but especially if you know you’ll be spending long periods on your feet. It shouldn’t be so soft to wear you sink in and there’s no support, but not too hard where it feels like you’re walking on wooden planks. You want a good in between that’s thick and cloud-like, but firm.
Boots with stability
Lastly but certainly not least, choose boots that are sturdy and stable, and easy to walk in. This means if opting for heels, the heel is thick enough that you won’t wobble while walking and ankles won’t give out, and if opting for flats, the sole is thick enough that it doesn’t feel like you’re walking on cement. You should look for this in boots no matter your age to keep yourself and your feet safe and protected.
12 best boots for women over 50
Keep reading for the best boots for women over 50 that are fashionable, comfy and supportive.
Aerosoles Epic Stretch Knee High Boots

Starting off strong, Aerosoles Epic Stretch Knee High Boots rank high on our list due to their comfort and supreme support. They feature a diamond flex outsole, OrthoLite foam insole, and a 2.5 inch heel for a bit of height sans the pain. Plus, the black faux leather contrasted with the black stretchy fabric not only looks stylish, but makes for the perfect fit for any calf size.
“I love a pointed toe but finding one that won’t pinch of leave me wanting to pry them off at the next given opportunity is rare—but I never felt that with these Aerosoles boots,” says Woman’s World Digital Director Julia Dennison. “Plus, the heel helps elevate a dress or skirt to the next level—while a rubber sole keeps them walkable. I really feel like I could walk from the restaurant to the bar in these and not bat an eyelash. I’ll be wearing them to a wedding this weekend and I’m pretty sure they’re dance floor-proof, too!”
Dolce Vita Raj Boots

Finding a pair of boots that fits your legs just right can be a challenge, as they often can look and feel too wide or too snug in the calf. To the rescue? Dolce Vita. To say we’re impressed with their sizing options would be an understatement; not only are their boots beyond chic, but they have a large variety of boots available in extra wide calf sizing, along with standard and wide calf sizing. One of our specific favorites is Dolce Vita Raj Extra Wide Calf Boots, which have a chic V-cut front at the top of the boot and a sturdy block heel. The brand describes them as “minimalist meets western” and we fully agree. Even more, it features a water-based leather alternative sock: practical and comfortable.
“The chocolate brown leather is perfect for fall and works with everything in my closet,” says Lauren Stachiw, Woman’s World Beauty Director. “They come in wide calf and extra wide calf and I went with the wide calf sizing, which gave me a bit more room for the perfect fit. I also love the western-inspired details and heel height—I’ll definitely be wearing these all fall and winter!”
Soul Naturalizer Orchid Knee High Boot

If you’re looking for a pair of boots that you can trust will hold up outdoors (but want something more stylish than the typical rain boots or hiking boots), look no further than Soul Naturalizer Orchid Wide Calf Knee High Boot. These are water-repellent, making them an excellent choice for days spent outside in the fall or winter, and better yet, they’re designed with soft foam lining, memory foam arch support, an antimicrobial sock lining and are lightweight and flexible. They are wide calf and have a small, 1¾” thick heel.
LifeStride Guild Tall Knee High Boot

We’re not sure these could be any more stunning. Lifestride Guild Tall Knee High Boot is made from beautiful faux leather microfiber material (we think this “bone” shade really pops, but it comes in black and brown, too) and features a chic side buckle and 2¾” heel. Best of all, it’s designed with the brand’s Soft System comfort technology, which gives you support, flexibility and cushioning for all day wear, and has a traction sole so you feel stable while walking. Bonus: They cost less than $100.
Franco Sarto Martin Knee High Boot

We hear you: You don’t quite want a flat, but you don’t quite want a full heel, either. Thankfully, Franco Sarto Martin Knee High Boot gives you the best of both worlds, with a small, baby heel that has just a 1.4” height. You’ll feel like you’re wearing flats, but have a bit of added height sans the pain. Plus, we love the unique design of this pair with its fold-over like style.
I tested these out by wearing them out to dinner in the city, and they didn’t hurt my feet all night. Even with its pointed toe, they still felt roomy and comfy for my feet.
Aldo Cadigoder Knee High Boot

The next two picks are sure to make a statement in the best way. First up, we have Aldo Cadigoder Knee High Boot. This crocodile skin design is ultra-trendy right now, but still looks timeless and classic. This pair is a bit on the taller side with a 3¼” heel (although the heel is thick), so proceed with caution if you’re not typically a heel wearer. Aside from the gorgeous design, we love that they’re made with dual density foam padded insoles.
Sam Edelman Uma Heel High Shaft Boots

Our next statement-making pair that made our list is Sam Edelman Uma Heel High Shaft Boots. In case you haven’t heard, red is the color of the season—and our favorite way to wear it is through our accessories! Sam Edelman is one of my all-time favorite shoe brands, and not just for the stunning designs—I love them for their comfort, too! I wore these out shopping for hours and honestly forgot I had them on my feet. They felt secure and sturdy, and I’ve received dozens of compliments every time I wear them. Best yet, they cost under $100 at Marshall’s.
LifeStride Brittany 50/50 Riding Boot

On the hunt for a comfortable riding boot? We’ve got you covered. Our pick is LifeStride Brittany 50/50 Riding Boot, which is oh-so-comfy for all your outdoor fall activities. Wear them not only riding, but to the apple orchard, pumpkin patch or other setting you’ll be outside on your feet. They have the full package with comfort, style and price, costing less than $100. They have a 1¾” stacked block heel, the perfect height, and a back stretch panel for easy mobility.
Dolce Vita Gyra Extra Wide Calf Boots

We just needed to reemphasize the incredible sizing options from Dolce Vita, thanks to their extra wide calf sizing. One of our other favorite pairs is Dolce Vita Gyra Extra Wide Calf Boots, which look especially stylish and sleek thanks to its chic square toe and luxe leather.
Clarks Octavia Up Cowboy Boots for Women

Cowboy boots are trending (did they ever really go out of style?), and we’re all for it—as long as they’re comfortable. Trust us, we’ve worn our fair share of painful cowboy boots and never want to go back. That’s not the case with Clarks Octavia Up Cowboy Boots for Women, which we can say with certainty are one of the best cowboy boots for women. Clarks is known for being a comfortable shoe brand, and not just by us; Thousands of podiatrists recommend them as well, so we trust this pair is comfortable and supportive. Plus, they cost just $60, a steal when it comes to cowboy boots.
Vivaia Athena Boots

Vivaia is a leader in our book when it comes to the knit/fabric boot options of the world. Vivaia Athena Boots are not only stylish, but one of the most supportive pairs of boots I’ve tried yet thanks to their pressure-relief, cushioned insole (meaning it’s great for weight distribution)—and this is coming from someone who’s on their feet walking in the city a lot. We love how this pair is dressy and fitting for formal occasions, but if you want a more casual look, they have many other colorways and patterns. And don’t worry about the fabric material getting in the way of your plans as it’s water-repellent.
Aerosoles Lasko Boot

Looking for comfortable booties? No problem. Aerosoles Lasko Boot is the perfect kitten heel bootie, largely in part to its stretchy material that ensures the perfect calf and ankle fit. Like its taller version earlier in this list, it has a diamond flex outsole and OrthoLite foam insole, making them comfortable to wear all day or night long.
I commuted from the city to the office in these and they kept my feet happy all day long.
Ugg Classic Slipper

We’re thankful to live in a world where slipper boots exist—and are considered stylish and trendy. You can’t go wrong with Ugg Classic Slipper, which will keep feet warm on the chilliest of days thanks to its plush wool insole. They’re super cushioned and comfy, too, making them a great slip-on boot to run errands in.
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