Best Comfortable Women’s Shoes for Fall
As we begin to transition our wardrobes into the next season, where better to begin than with our shoes? As sandal season fades and cooler weather creeps in, finding a comfortable pair for my over-60 feet can be a real challenge. I know many of you in the AWSL community feel the same way while shopping for stylish shoes to keep up with your changing feet. Today, I’ve rounded up some of the best comfy yet fashionable fall shoes, including some of my personal favorites, so we can all step into the season feeling great and looking fabulous.
Need other comfortable shoe recommendations? Check out these posts:
- Best Hiking Shoes and Boots for Women
- Where to Buy Narrow and Wide-Width Shoes for Women
- Most Comfortable White Sneakers for Women Over 60
- Best Sneakers and Walking Shoes for Mature Feet
My Favorite Comfortable Women’s Shoes for Fall
There are lots of options when it comes to women’s shoes for fall, and the comfort varies tremendously. Here’s what I’m personally gravitating to. I’m willing to spend more on comfy shoes because I will keep and wear them for many years. In fact, I’ve got shoes that are over 25 years old, which I store in their original boxes.
Slip-on sneakers with lots of flex and cushioning go next level when the upper is made from perforated microfiber, which stretches over any sore spots on your foot. I find these Ilse Jacobsen Tulip slip-ons a bit like Lay’s potato chips…it’s hard to stop at one. They come in endless color options and can be machine-washed.
Boot season is easily one of my favorites! I find boots and booties to be some of the comfiest footwear options for fall and winter—they hug your ankle for added support and keep your feet warm and dry when the weather gets messy.
This year, I needed a fresh pair of booties, so I picked up these low-heeled Munro booties. Their simple, minimalist design, almond-shaped toe, and neutral color make them an easy match for just about everything in my fall wardrobe. You can see them styled with three different styles of denim in this post on 2024 trends. Their block heel adds a bit of height but is still super comfy and stable to walk in. They come in sizes 5-11, medium and wide width. Their sizing, along with cushioned insole, as made Munro one of my go-to brands for many, many years.
I share all of my tips on wearing ankle boots over 50 in this post.
Ballet flats are having a moment—again. But honestly, did they ever really go out of style? To me, they’re one of those timeless staples you can always count on. This season, Mary Jane and slingback variations are popping up everywhere, adding a twist to the classic ballet flat.
I’ve been wearing Rothy’s flats for years and love this new Ballet flat style. These come in 6 colors and are machine washable. They’re knit with Rothy’s signature thread, which is spun from recycled plastic bottles.
I have these Margaux Demi ballet flats in 3 colors and consider them sort of perfect. I love that they come in wide and narrow widths, sizes 3-14. They’re totally classic, and the adjustable cord bow allows me to loosen it on my left foot for even more comfort over my bunion.
Clogs are a great fall shoe option that’s easy on the feet. I started wearing them back in the ’70s, and it’s fun to see the same classic brands still going strong today. One of my all-time favorite brands is Dansko. Last year, I added these Sassy cutout clogs to my fall wardrobe. I love the bit of extra height they give me, along with the stability from the enclosed heel and buckled strap.
Loafers are always popular for fall. This year I’ve seeing them in both sleek and chunky-soled options like this one from Naturalizer. I like the visual balance they provide with the straight-leg and wider-leg pants that are also popular this year. They’re a great option for every day with jeans or trousers, and they dress up easily depending on the leather. There are also a lot of options available in the “comfort” category with this chunky loafer, which is good news for those of us with tricky feet.
I’m also a huge fan of driving mocs because the leather is super soft and the soles are very flexible. They frequently have rubber pebbles on the bottom of the shoe to grip the pedals, which makes them extra cushiony to walk in.
And then, of course, there are casual sneakers, which I only embraced as everyday shoes when I bought this pair of Ecco Soft 7 sneakers back in 2018. Before that, I only wore sneakers to work out. Now, I have quite a collection in various styles, shapes, and, yes, colors. You can see some of my favorites in this post and this post.
I wore these leather sneakers all over Japan years ago and a hundred other places since. They’re super comfy with a removable innersole, which gives you space to add your orthotic or to adjust the width. The Ecco lace-ups come in a wide selection of colors, but black goes with absolutely everything and is great at hiding scuffs and dirt.
I have a small collection of white Paul Green sneakers and love them. I found these totally classic-looking Carly low-top style on being price-matched earlier this year and snatched them up. They’re one of my go-to sneakers these days, and I love that they’re made with a soft terry lining, which adds to their appeal and comfort.
Platform sneakers continue to be super popular for fall and are a great way to add some height, especially if you’re petite like I am. The insoles also often extra cushioning which my tired feet appreciate.
Do you have a pair of go-to shoes for fall? What shoes are on your radar for fall? Let me know in the comments.
Jennifer, I am wondering if you’ve tried the Rothy’s Drivers yet. If yes, what do you think? I’ve got them in my cart but still on the fence.
I have not yet, but my daughter has them in olvie and she loves them.
Alas, I cannot wear most of the styles you show here. I use orthotics in my shoes and most of these shoes don’t come up far enough on my foot to be able to walk in. I do love the styles though. However, I found a pair of ECCO sneakers a few years ago that are so comfortable that I bought 3 pairs. I’m glad I did, because I have not found another pair even by ECCO that fit me well. Did i fail to mention I am also Narrow width? Very few shoes are now made to fit me.
I never had luck with Sketchers until I tried on their new slip in shoes. Wonderful for my painful, arthritic, post surgery feet. Thanks for the great ideas, Jennifer!
Jennifer,
When I click on the link for items, it just takes me right back to your post. This has been true for several days now. Is there something I can do?
Thanks,
Julie
I’m not sure why that would happen. Let me check into it.
I am always looking for recommendations for comfortable shoes and sneakers. I bought my first Vionics. Uptown slip on leather loafers recently and have been loving them. I purchased my regular size in medium width. These do not squeeze the wide part of the foot unlike some loafers after wearing awhile. The leather in the back of the shoe is soft and unstructured which does not compromise the support of the shoe. I intend to try other Vionics in the future.
That’s great to know, thanks Linda
I try to only buy natural fibers. I just think they look more expensive. Having said that, I found some cute, fabric, leopard flats at TJMaxx. $25, btw. Worth it to have some fun with leopard. Super comfy, but to my surprise, by the end of the day the fabric had stretched so much they were falling off. I love loafers. No platforms or chunky soles. I wear my shoes for years and want them to look timeless. I ordered a pair online last week. I will never order shoes online again. I must have difficult to fit feet.
Great post on comfort shoes. Appears the Organic Collar Caslon cardigan is back in stock? Did you go with a small or medium. Such a cute basic sweater for fall!
Thanks!
Amazing. I’m wearing a M
I have my white Easy Spirit Denise Austin Mel sneakers on right now! Great for dog walks. I need cushioning and wide width and these have many colors as well. On days when I feel I need more support, I wear my Brooks Ghost Max sneakers. I wear 7W and need cushion and room for my arthritic toes. I bought a pair of the Brooks in black for winter walks. I have many Skechers in different colors and styles and tend to wear them at home.
Have been a HUGE Rothy’s fan for a decade. For my 75 yo bunions they are the softest, easiest and most attractive shoes ever. The round toe and the loafers are the most comfy on my feet. Tried the tennis shoe but the edge where the top and rubber bottom meet rubbed my baby toe.
Anyway….try them! I have 11 pairs
Amazing! Thanks for letting us know. I only have 2 pairs and will add more now.
You look so pretty today! I looked at the Caslon cardigan on N website, and it has been restocked. Really nice looking cardigan.
That’s awesome, it’s a great little cardigan
I have really bad feet, and need lots of support, width, and padding. For several years my go-to sneaker for fall and winter has been the Easy Spirit “Romy.” They’re leather, and have all the features I need. For the warmer months I love the Easy Spirit Denise Austin “Mel” sneakers. This style is mesh. Both styles come in many colors.
How do you price match tennis shoes? I love those Paul Green sneakers but would love to get them at a reduced cost.
I enjoy your blog. I look forward to it every morning. Thank you for bringing us wonderful content.
Nordstrom will match the sale price when other retailers put thignsg on sale. I keep an eye out here for brands I like.
I really need to think about shoes for fall. Since having foot problems I’ve just kind of been living in tennis shoes. I really like the boots and loafers you posted. This was a much appreciated post. Thanks 🌺
Just for the benefit of others…tulip slip-ons are not great for cobble stone streets.
I bought a pair of Ilse Jacobsen tulip slip-ons (black with black soles) for a trip to Europe thinking they would be as comfortable as sneakers but a little less casual. And yes, they are very comfortable. However, I did not find them suitable for cobble stone streets. The soles are cushiony soft, but as a result I could feel the uneven cobble stones with every step. I ended up wearing sneakers after all as they provided more stability.
Wow, that’s good to know. I never thought of that issue
The black sweater and jeans with black loafers is a great look for you.
Thanks Linda
Jennifer, this is totally off topic, and you don’t have to publish it. I am trying to get creases out of faux leather pants and was wondering if anyone has any suggestions that have worked. These are deep creases as I folded them in a drawer over the summer. I’ve tried a hairdryer (on medium heat) on the inside of the pants, but that didn’t work and I’m thinking of trying a steamer, again on the inside of the pants. Any suggestions would be appreciated.
Try popping them in a hot dryer for a few minutes and the smooth out on a flat service to cool. Anyone else have a suggestion?
Great post, you have it covered. Want to share I’ve had great luck with Franco Sarto from Norstrom/Rack. I’ve added two chunky loafers (not leather but comfy, will be great for bad weather) and a modern leather flat (second color is on my wishlist.) I have wider feet. Ballet flats with bows just aren’t my style. 😉 One other rec is the Ecco Soft sneaker in a metallic. I have silver and they are my “dress” sneakers. I love loafers and I couldn’t be more excited for the return of socks allowing for winter loafer wearing!
I love my Ecco Soft woven sneakers in metallic too!