Comfortable Stylish Fall Shoes & Boots for Women Over 60

I am joining my friend Kim for our monthly Signature Style series. This month we are talking about fall shoes and boots. My rules for fall shoes are simple at this stage of the game. Boots get a flat sole or a very low heel, and shoes are flat. I’ve done my time in high heels. These days I’d rather walk all day than stand still looking fabulous. I have a bunion and plantar fasciitis (the glamorous realities nobody puts on Instagram), so a cushioned insole isn’t optional. It’s the first thing I check.

The good news? Comfort shoes have come a long way. Within my rules there’s still plenty of room for texture, color, and personality, which is where the fun is. And after years of trying everything, one of my favorite brands for all day comfort is Gentle Souls (not sponsored) They make shoes I actually want to look at that still feel good at the end of the day. Let’s take a look at all my favorites.

What I Look for in Comfortable Fall Shoes

Our feet change as we get older (nobody warned me about that part), so here’s my checklist before anything earns a spot in my fall wardrobe:

• A cushioned insole with good arch support. Non-negotiable with plantar fasciitis. A removable insole is a bonus, so you can swap in your own orthotic.
• A roomy toe box. Almond toe and square toe shapes give a bunion breathing room without looking clunky. If you have wide feet, look for brands that offer wide widths. Do yourself a favor and buy stretchers. You will thank me later.
• A low heel height. Flat or a low block heel for boots. If I want a little lift, I look for a cushioned heel under two inches.
• Side zippers or elastic side panels. No more sitting on the bedroom floor wrestling a boot on.
• Soft leather or suede and flexible soles. No painful breaking-in period after the first wear.

The Comfortable Flats I Wear on Repeat

Gentle Souls Salco Suede Driver

If I could only keep one pair, it would be these. They are the most comfortable shoes I own right now, and my everyday shoe for running errands. A driver is the closest thing to wearing nothing at all, and in suede it still looks pulled together with barrel-leg jeans and a great sweater.

Gentle Souls Sophie Loafer

The Sophie is my dressier pick among comfortable loafers. The suede is buttery and the square toe is modern, which also gives my bunion some room. Some say they can run big, if you are in-between size try a half size down.I wear my usual size 8. I own these in brown, green and red.

Naturalizer 27 Edit Carla Ballet Flat

I love a great ballet flat, but most of them are murder on a bunion. The Carla is the exception. It comes in wide widths, the square toe gives my foot room to breathe, and the cushioned footbed means I can actually wear them all day. They come in a whole range of colors, and textures, and the price point is reasonable enough that I don’t feel guilty owning more than one. I own the two above and love them with pants or jeans and a great sweater.

My Favorite Ankle Boots and Tall Boots

Gentle Souls Emma Bootie

For pure all day comfort, the Emma wins. It’s a clean suede ankle boot with a side zip, and it goes with everything from barrel jeans to midi skirts. It’s the boot I grab when I know I’ll be walking across a giant parking lot and then standing for hours. This boot is my everyday boot and it is oh so comfy. I own it in three colors and it is still available in suede. I walked all over France in these.

Gentle Souls Emma Stretch Boot

The knee-high version of my favorite. The stretch shaft hugs the leg without squeezing, and the top of the boot hits just below the knee, which I think is the most elegant height on us. It’s my go-to for the cooler months. This one is now only available on resale sites which is unfortunate. There are several on eBay here., and on Poshmark here. Grab them while you can!

Gentle Souls Ella Stretch Boot

When I want a little height, this is the one. The heel is a touch higher than my usual, but it’s so well cushioned that I forget about it. It also comes in a wide-calf version, which many of you have asked about. (Measure the widest part of your calf before ordering.)

Ariat Cowboy Boots in Wide Width

I love a little western chic (give me western-inspired boots and fringe over plaid any day), so I couldn’t leave out my two pairs of Ariat cowboy boots. I’ll be honest: they’re not as comfy as my Gentle Souls. But they’re pretty darn comfy especially after they are worn in, which for a cowboy boot is high praise. The secret is ordering them in a wide width. If you have wider feet or a bunion, that extra room in the toe box makes all the difference, and a good leather cowboy boot molds to your foot the more you wear it. The low stacked heel keeps them within my rules. I wear mine with wide-leg jeans and a chunky sweater, or with a midi skirt when I want something a little more unexpected.

Naturalizer 27 Edit Brooke Knee High Boot

If you want a Western look without going all in, the Brooke is the answer. It has a snip toe and Western-inspired lines, but the low block heel keeps it walkable and polished enough for a dinner out. A side zip and a hidden stretch panel make it easy to pull on, and the cushioning feels like it belongs in a much more expensive boot. Best of all, it comes in wide, and extended calf sizes, so there’s finally a tall Western boot for those of us who have given up squeezing into one. They would look great with a midi skirt or tucked under straight-leg jeans.

EDITOR’S NOTE: Many Gentle Souls styles are on sale at QVC right now here. I don’t link to QVC often because their links usually expire when a special ends, but this one is too good not to share.

On My Fall Wish List

I’m on the hunt for the perfect navy suede boot to wear with denim. It feels softer than black and plays beautifully with olive, camel, chocolate brown, and other neutral colors, but a truly comfortable navy boot has been surprisingly hard to find.

Aquatalia Ulyssa Suede Bootie

This is the one I most want to try. It’s made in Italy, comes in navy, is waterproof, and has a hidden wedge, which I suspect is the trick for a little lift without pressure on the ball of the foot. The toe isn’t too pointy which I like. It’s an investment, so I need to do a little more research. The reviews are strong.If you own them please share otherwise I will report back on whether it earns its place.

Gentle Souls Namaste Stretch Boot

Another stretch suede bootie with a low heel and a side zip, and yes, it comes in navy too. I’m seeing it as the more updated sister to my Emmas. I keep begging GS to send me a pair so far no luck!!

Naturalizer 27 Edit Dawn Mary Jane Flat

Mary Janes are having a moment, and the Dawn is the version I’ve been eyeing. It’s soft suede with a square toe, an adjustable buckle strap that keeps it secure without pinching, and extra cushioning underfoot. Like the Carla, it comes in wide, which makes it a real contender for anyone with bunions. At this price point, it might not stay on the wish list for long.

Gentle Souls Sophie Cozy Suede Driver

My Salco drivers have spoiled me, and the cozy version of the Sophie looks like the perfect pair for chilly mornings . It comes in several colors.

Gentle Souls Nalston Suede Bootie

This sleek, sock-like bootie with an almond toe is the dressiest of the bunch, and I can already picture it peeking out from under wide-leg trousers. Reviewers say it runs large, so size down a half. if you are in-between sizes.

Insoles

Let’s face it some shoes need a little help when it comes to comfort. That is where insoles come in. I have found these to be helpful in boots, and these for flats.

Shop my Favorite Comfortable Fall Shoes and Boots

The Last Word on Comfort

One of the best parts of this stage of life is that we get to make our own rules, and mine say comfort and style belong together. I hope you found a pair or two to try this fall (and permission to finally retire the shoes that hurt). Mine have all left the building.

What are your favorite comfortable fall shoes and boots? Is there a brand you swear by for bunions or wide feet? Please share your thoughts in the comments, because your recommendations are how I find my next favorite pair! And if you have a friend who’s been hunting for chic shoes she can actually walk in, please share this post with her.

Don’t miss Kim’s favorite fall shoes and boots over at Northern California Style! Pssst she doesn’t have any foot issues yet so she will feature some that I can’t!

This post contains affiliate links.

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Northern California Style