10 of the most comfortable walking shoes for the stylish woman

by Sylvia

most comfortable walking shoes for women | 40plusstyle.com

Much like Sylvia in her travel adventures, I love to get out and explore when I’m on a trip. But when I walk too long, I often end up with blisters and a sore back, legs and feet. I finally figured out that lightweight shoes with good sole support and padding are a lifesaver. Here are 10 of the most comfortable walking shoes I’ve found. They’re also fashionable, pack well and versatile enough to dress up or dress down.

Before I share, I wanted you to know that I chose shoes that are also cool for spring and summer walking weather. I avoided choosing gym shoes or track/workout sneakers as the obvious choice so you can wear  them with shorts or a lovely dress.

1. Ecco Damara Sandle, $119.95

most comfortable walking shoes for women by Ecco | 40plusstyle.com

I love the fashionable, two-tone look of these sandals by Ecco and the wide, fabric strap for extra support. They breathe nicely on a hot summer day and have some good contouring at the soles. They also come in single colors, like the silver pair the model wears in the main image.

2. Keen Sienna MJ Canvas Slip-Ons, $90

stylish travel and walking shoes for women | 40plusstyle.com

When you want a closed-toe flat for a little extra foot protection, you’ll like these Mary Janes. Or maybe you’re pedicure needs a refresh and showing off your toes is not ideal. These MJs are made with heavy-duty canvas that still manages to be lightweight and don’t get too hot. The footbed is made with shock-absorbing cork. They come in a rainbow of colors, too. I chose this mint, but there are color choices for every style personality.

3. OluKai Upena Sandal, $89.95

most comfortable walking shoes for summer travel | 40plusstyle.com

If you’re part of the 40+ Style Club, you know we focused on learning about color theory and the metallics trend in fashion. These chic and comfortable walking shoes have a metallic touch to them that add just a little fashion and elegance to their style. They’re also available in other colors and tones.

4. Naot Kayla Sandal, $134.95

Most comfortable wedges for travel | 40plusstyle.com

Naot makes wonderfully comfortable walking shoes in a variety of fashion-forward styles. This style is especially great because of the colors, adjustable ankle strap and the slight wedge that gives you a little bit of extra height without sacrificing comfort.

5. Dr. Scholl’s Vienna Slip-On, $88

best travel shoes | 40plusstyle.com

This special burgundy color is one of five colors you can find these in. You can also go with a classic black, white, beige or a taupe shade. The insoles of these slip-ons are made with memory foam, which make these one of the most comfortable walking shoes you’ll ever try on.

6. PIKOLINOS Alcudia Lace-Up Gladiator Sandal, $159.95

fashionable walking shoes for travel | 40plusstyle.com

Want to add a little extra style to your look? These gladiator sandals are perfect. They have a 1″ inch heel, a quick zip-up back and laces that tighten to adjust to your feet.

7. Chaco Cordova Sandal, $90

Summer walking shoes for women | 40plusstyle.com

If you want a minimalist sandal with no ankle straps or toe straps, these lovely leather sandals by Chaco are a definite upgrade from a flip flop. These are well padded everywhere, especially inside the contoured soles. There are 5 neutral shades to choose from.

8. Cole Haan ZERØGRAND Wingtip Oxford, $139.95 to $200

Most comfortable walking shoes for stylish women | 40plusstyle.com

When you want to dress up a little more or prefer to avoid sandals, why not add some whimsy to your feet? You’ll be pleasantly surprised to know that this suede is lightweight and weather proof, inside and out. Maybe that’s why these are one of Cole Haan‘s best selling shoes. I’ve shared the neutral gray pair in the image, but there’s even a bright hot pink tone available!

9. SÖFFT Mirabelle Sport Sandal, $78.95

comfortable travel sandals | 40plusstyle.com

These sandals look great with everything from shorts to jeans to a dress. The indigo tone is especially unique and a fun look when you’re out and about.

10. Ainu Malini Sandal, $94.95

most comfortable travel sandals | 40plusstyle.com

This hybrid sandal style features a strappy, leather look to keep your feet cool in summer with a closed-toe front that protects you from stubbing your toes on your walking journey. The leather is lined on the inside for extra comfort. The cork insole is soft and comfortable and a rubber sole grips nearly any road surface well.

Which of these ten stylish and comfortable walking shoes would you wear?

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Oooh.. nice choices!


I personally wouldn’t wear any of those. To my eye they are almost all ugly.

My favourite footwear brand from a comfort and style POV is Vince Camuto. Incredibly soft leather, surprisingly comfortable despite the heels, and the pairs I have (several colours of the ‘Lavette’ Perforated Peep Toe Bootie, and the Vamelia, and the Brianny) are not dated.


I tend to agree about the aesthetics—these aren’t very attractive to me. I happen to like nicer leather sandals in brown or white (summer) and Hush Puppies Chaste leather ballet flats for anytime and my black Sam Edelman riding boots have been the most comfortable for walking/traveling in the winter. When I throw in a pair of comfortable tennis shoes, I can go almost anywhere in some basic semblance of style.


I love Danskos for comfortable casual shoes. I don’t always love the way they look, but they are getting better at incorporating some style. I buy Cole Haan for dressier shoes because they do stylish designs with more comfort than most brands.


Thank you for such a lovely selection, Cynthia! I can’t choose one style. I like the variety you offered and would wear nearly all of them. Except the lace up ones which are very nice but maybe too trendy for my style. It’s refreshing to see a blog showing ACTUAL practical shoes and not pushing uncomfortable ballerina flats and trendy designer shoes as “comfortable”. Would love to see more like this!


Nice selection of shoes … looks like I’ll need to update my rotation soon!


I am still looking for good ones, but already found a few.

Janice M.

The shoes you show are lovely – HOWEVER – I have narrow feet and none of these shoes will fit me. It’s a real problem. The shoe companies seem to think everyone has medium width feet

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