Comfortable Fall Shoes That Look Modern in 2025
It’s that time again when I’m almost ready to pack away my sandals, but not quite ready to pull out the boots. The mornings feel like fall, the afternoons still say summer, and my feet are somewhere in limbo.
So I’ve been looking for comfortable fall shoes that look modern in 2025—styles that feel good all day and still look pulled-together. Not overly trendy. Not orthopedic. Just real-life wearable shoes with a little polish and personality.
If you’re curious, you can still read last year’s guide here, which many of you found helpful. But this post is a fresh take—filled with what’s catching my eye for this season, including some old favorites in new colors and a few new brands I’m trying out.
Paul Green
I bought my first pair of Paul Green shoes many years ago, and I’ve been a fan ever since. They’re handcrafted in Austria using beautiful Italian leather, and the quality has stayed consistently high over the years. They’re expensive, but I find them incredibly comfortable, so they’re worth the splurge for me.
Their styles are understated, modern, and incredibly comfortable—no breaking-in required. I recently added a pair of blue suede sneakers that nod to the retro trend without feeling costume-y. They’ve been on heavy rotation lately, adding a sporty edge to jeans and casual pants while keeping my feet happy.
Easy Spirit
Easy Spirit has been around for decades, and I’ll be honest, some of their styles still lean frumpy if you’re not careful. But when you find the right pair, they’re wonderfully kind to your feet. The Sidney boot is one of those gems. It’s sleek, lightweight, and has enough cushioning to get me through a long day comfortably.
I also like the Morgan lug-sole bootie for a more rugged look—it adds a bit of edge and the sole gives extra support, which I always appreciate.
You do have to pick and choose with Easy Spirit, but when it works, it really works.
Margaux
I’ve been wearing Margaux shoes for years, so when I spotted the Phoebe Mary Janes, I didn’t hesitate. I slipped them on for a full day of shopping, walking, dinner out…and didn’t think about my feet once. That’s always the goal.
They come in sizes 4–13, with narrow, medium, and wide widths. Mine are wides, and they were comfortable right out of the box. No break-in period, no regrets.
I traveled home in them yesterday, and they felt polished and comfy all day.
Eileen Fisher
I’ve been wearing Eileen Fisher shoes for years because they strike that rare balance: minimalist, modern, and very comfortable.
Her knit booties have been favorites in my fall wardrobe, especially the Purl Sock Bootie. I loved them so much I bought a second pair when I spotted them on sale last year. They hug your foot, stretch where you need them to, and don’t aggravate any of the usual foot issues…bunions included.
This season, I’m eyeing the Paron Crepe Stretch Wedge Bootie. The square toe, soft knit, and low wedge make it look modern while still being forgiving and wearable. If your feet are sensitive, this is a brand worth trying.
Naturalizer
Naturalizer has come a long way from the plain styles many of us remember. These days, their loafers, boots, and sneakers look more current, while still being kind to your feet.
I especially like their block heels, which add a bit of height without sacrificing stability. They also offer wide widths and multiple calf sizes, which makes finding a good fit a lot easier.
This fall, I’m keeping an eye on a few standouts: a classic knee-high boot with a cushioned insole, a polished tassel loafer, and a fun animal print Mary Jane flat that adds personality without going over the top.
Birdies
Every fall, my Birdies Velvet Starling loafers come out and go straight into rotation. They feel like slippers but look polished enough to wear with jeans or even dressier outfits.
Birdies carries flats, loafers, and even boots, all built with their signature cushioned insole. If you’re after comfort that doesn’t look too casual, they’re worth a look.
Vionic
If arch support is at the top of your list, Vionic is hard to beat. Their shoes are designed with built-in orthotic technology, which makes a huge difference if you spend a lot of time walking.
For fall, I love the look of their Cleo Loafer and Heloise Mary Jane Flat. They look polished but give you the support of a walking shoe. If you’ve struggled to find shoes that don’t aggravate plantar fasciitis, this brand is worth exploring.
Ecco
I’ve been wearing and loving Ecco shoes and sneakers for years. They’re a Danish brand that has built a reputation for combining comfort technology with soft leathers and minimalist design. Their Soft 7 sneakers are a longtime favorite that has plenty of arch support, cushioned soles, and a clean silhouette.
Rothy’s
I’ve been a fan of Rothy’s since my first pair of leopard print flats. The idea of shoes made from recycled plastic bottles sounded gimmicky at first, but somehow, they’re soft, flexible, and surprisingly comfortable.
They’re also machine washable, which is very helpful. If you like shoes that feel light, pack easily, and require zero break-in, Rothy’s are worth a look.
A Few More Fall Shoes That Caught My Eye:
Now I’d Love to Hear From You
These are just some of the comfortable shoes that have caught my attention for fall, but there are plenty of other great brands out there. Cole Haan, Franco Sarto, Aerosoles, and Sam Edelman all offer options worth exploring if you are looking for shoes that strike a balance between style and comfort.
I know many of you have your own tried-and-true favorites, and I would love to hear about them. Are you adding new boots, loafers, or Mary Janes to your wardrobe this season? Or are you sticking with a classic pair that has served you well for years?
My favorite, most comfortable shoes are Naots!
I love your shoe selection, but many of them are too expensive for me. I need good arch support and cushioning for under $100. Any recommendations?
Thanks
I’m not sure but I think adding cushioned inserts with great arch support will help all shoes be more comfortable.
I love Paul Green shoes but they really have gone up in price that I’m looking else where for comfortable shoes. Thank you for your selection of shoes for our perusal!
Really nice fall shoe choices. I like the Naturalizers. I really like the look of a driving moc and there are a couple of choices. Your outfit in the Eileen Fisher Purl boots is so classic and so much my style, you look great!!
Have you tried Mephisto? They have great shoes and you can wear them all day.
Best of luck finding the perfect pair
Yes, I love them
My favorite boots are a Canadian brand, Blondo, I have 3 pair, love them all. The suede is good quality and cleans up well. They are all waterproof, I put them through the test in Amsterdam and London.
No Mary Jane’s or Loafers for me. Loafers look like I’m wearing my husbands shoes 😄.
Lots of nice suggestions Jennifer thank you!
lol!
Who makes the black blazer you are wearing in the shot with the Rothy’s? I really like its structured look. TY! As an aside, I’ve learned so much from your posts — and I’m still learning how to update my fashion / skin care / etc. choices at 83. My short, coarse, porous hair is salt and pepper — mostly pepper (ugh), so my stylist has woven in a lot of silver highlights. They’re beautiful, and I’d like to keep them that way. I’ve been using purple shampoo / conditioner / hair oil for a long time, but the “salt” part of my hair still manages to brass up. I’ll give your Opalex recommendation a try.
It is this Regent blazer
TY! There is a store near me, so I’ll check it out.
Going to try your shampoo for keeping the yellow out of white hair. I did get the Oleplex Bonding shampoo and really like it. Shoes are so difficult for me as my toes are all deformed from arthritis and I have very high arches. My walking sneakers are Brooks. I even bought my husband a black pair and a white pair. I have three pairs in white, grey and black. On the hunt for navy swede sneakers in 7W. I have Ecco, Easy Spirit and Skechers which I often change into and out of several times a day. I would love to try the lug soled Naturalizer loafers. I just got 6 more plastic shoe containers and they are full. Every time I see your feet in Mary Jane’s I think of my years in ballet. I can’t wear ballet flats at all anymore. Sigh.
New Balance 321 sneaker (walked 9 miles in them one day), great for wide feet: Sam Edelman Lorraine and Lucca loafers, Eastland Patricia driving mocs, Everlane day glove flats. I’ve been freezing in the office lately with sandals!
I wondered about the Everlane Glove, it looks so chic. Thanks Shari
These are all great shoe picks. I’ve been thinking about fall shoes but had no idea what I wanted. These options are great. I can’t seem to wear sandals anymore so I stuck to trainers for most of the summer. At age 75 comfort is crucial.
My feet demand comfort now too
I just purchased a pair of white sneakers (Ecco). What product(s) do you use to keep them clean and white?
I use the Mr Clean Magic Erasers! Great product
I’d like to give a shout out for Vivaia shoes. I’ve been a fan of these really comfortable shoes for 4 years now. I particularly like their square toe ballet flats. I have the basic black and also navy blue, but when on sale pick up leopard and other fun prints. They are mostly sold online but I noticed they now have one storefront too.
P.S. I love the gorgeous green vest in the Morgan Lug (sp?) picture!
I’ve heard very good things about Vivaia and they look stylish
I definitely have to buy those Margaux mary janes in the leopard print. In the past even the narrow sizes of a Margaux has been too wide for my very skinny foot but I’m going to give them a try because they’re so cute!
I hope they worok for you. Margaux is so comfy
Suffering from Achilles tendonitis, I have lived in these SAS shoes: Cozy Adjustable Slides, Relaxed Sandal, and I have just received Clog Comfort Slip on for my fall wardrobe. With the softest leather, they are stylish, but oh so comfortable right out of the box .
I discovered RYKER on a recent trip to Canada. They are very comfortable for my Plantar Fasciitis issue…I can no longer wear flat shoes and need a wedge/lug/sneaker/block heel…ugh…
You look beautiful in all of these pictures. I love the
shoes you have chosen…Could you please tell me how
you keep the yellow out of your hair. It is a great cut..
I simply use this purple toning shampoo about once every two weeks.It works really well.