I try on a LOT of shoes. In preparation for my giant go-on-forever comfort shoe posts, I not only spend weeks and weeks online researching the most current styles in comfort shoes, but I also try on tons and tons of actual shoes. I go to the stores and look at the actual shoes in person, I order a ridiculous number of shoes to the house and try them on in my bedroom, and I give quite a few shoes true-life trials walking the city pavement, standing around on playgrounds, and occasionally running faster than what is flattering to retrieve sports balls that have rolled into various settings they are not welcome.

15 Pairs of Comfortable, Stylish Shoes I Tried This Season

So, here are 15 of the ones I’ve tried…complete with the good and not-so-good of each one. All fit me surprisingly TTS unless otherwise mentioned.

**AND because this post took me so long to put together…many are ON SALE NOW! I love when my procrastination ends up in our favor!**

1. Kork Ease Kanai Bootie (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom (On Sale)

Pros: These are REALLY comfortable. The studded detailing is such a cool addition. They feel and look great on. To me, these are totally the balance between comfort and style at its best. I like the brown a lot, but the gray and black are also really good. A great everyday bootie from a well-known comfort brand that’s REALLY good at making feet happy.

Cons: Obviously if you’re looking for a high heel, these aren’t your shoes. They definitely have a very flat look. Because of the angle of your foot with the slight heel, though, they are more comfortable for me than actual flats.

2. Dr. Scholl’s Snake Print

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom | At Dr. Scholl’s

Pros: Woohoo for snake print booties from a well-known comfort brand. I’ve been walking the city in these, and they have decent arch support and plenty of cushion. A fun addition to give any simple outfit a little more oomph. From Dr. Scholl’s sustainable line.

Cons: If you look closely in person, you can tell that the material is not as high quality as some of the higher-end brands, but for the price and comfort…I’ll take it.

3. Fly London Yeni

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom

Pros: These Fly Londons in dark petrol have turned into one of my everyday booties. Fly London is one of my favorite brands for REAL comfort. These end up being more comfortable for my feet than many sneakers. I can walk the city sidewalks in these all day long with no issues at all. These come in black and brown, but I’m into the unexpected blue/green of the dark petrol that goes with everything, but is just a little different. I get compliments every time I wear them.

Cons: I know Fly London style isn’t for everyone. They’re a bit on the funkier side of things style-wise, rather than the super on-trend side of things. I’m, however, okay with that, especially when it means super, super, super comfort. When I first tried these on, I thought I was going to need to size up, but I was so excited to wear them immediately, I kept my regular size; I’m glad I did because they’re fine.

4. Dansko Hayley (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Zappos (On Sale) | At Amazon (Some Sizes On Sale)

Pros: So super comfortable. You know that my feet LOVE Danskos, so it’s hard to turn any pair away. Good arch support and a nice cushioned footbed. These have a nice easy-to-wear-with-everything vibe.

Cons: I’m not wowed by the color options–this tan is absolutely fine, but I’m drawn more this season to the richer warmer browns. Also, it makes me sad to say this, but not everyone’s feet love Danskos. I don’t know how this is possible (because mine LOVE them), but you gotta listen to your feet!

5. Sandgrens High Heel Clog in Fudge

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Amazon | At Etsy

Pros: The other shoe (besides the Fly Londons) that I’ve been wearing on the daily. They don’t have a cushy footbed (like Danskos), but my feet like them (especially with thick socks) and I’ve walked miles and miles in them with no foot-aching issues. I love the dark brown color in addition to the darker wood base.

Cons: I wish the boot shaft was a tad bit skinnier (like these Lottas). The ankle IS somewhat adjustable on the Sandgrens, though. The Lottas feel a little more like a high heel and the Sandgrens feel more like an everyday shoe in terms of walkability and balance.

6. Sanita Juna in Cognac

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Zappos

Pros: The color and leather is gorgeous. So so pretty! These are the best shade of brown of all the shoes I tried, and I really liked the heel height. They don’t have a cushioned footbed, but they’re quite comfortable (as long as you’re a traditional wooden clog fan).

Cons: Way too wide of a boot shaft for me, and I don’t even have skinny ankles. The boot shaft just looked funny to me…not clear on how I would style them. Maybe with skinny jeans and a big bulky sweater/coat to balance them out? I was hoping to wear them with skirts, though, and they just didn’t look right.

7. El Naturalista Trivia in Wood

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Zappos

Pros: The weight distribution is really good with these. The heel is somewhat high, but VERY comfortable because of this really good weight distribution. The heel on this boot is interesting, cool looking and unique. Because of the higher (more sock-like) shaft, they work well with skirts or even under straighter jeans.

Cons: The foot bed isn’t very cushy, but because of the weight distribution, they’re still plenty comfortable. The material and color is fine, but not AS pretty as some of the others.

8. UGG Tall Boots

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Zappos | At Nordstrom

Pros: Gorgeous leather (prettier color in person), a VERY pretty heel, and decent (but not amazing) arch support.

Cons: Not enough cushion in the footbed (for my preferences), felt a bit heavy, and the material was not as flexible as I wanted it to be. Felt fine when worn with thick socks, but ultimately I decided I liked these Gentle Souls better.

9. Dr. Scholl’s Slouch Boots (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Zappos (On Sale) | At Dr. Scholls (On Sale)

Pros: Super comfortable. Soft material and feel great on. Love that some of the comfort brands are getting on board with trendier styling. Plenty of support and cushion for walking.

Cons: Wish they came in more colors. I like this light tan, but would have preferred a richer brown. As with Dr. Scholl’s snake print, I feel like you could see that they’re not as good of quality material as some of the higher-end brands, but then again….it’s nice they’re not $600!

10. Gentle Souls Tall Boots (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Amazon | At Zappos (On Sale) | At Nordstrom (On Sale-limited sizing)

Pros: These were my favorite of all the tall boots I tried. The material is soft, the suede looks totally luxe, and it’s a really beautiful color. These photos don’t do them justice. The clean simple styling is perfect. In addition to being the prettiest color and material of the tall boots I tried, they are also the most comfortable. Soft cushioned foot bed and totally walkable heel.

Cons: A bit pricey for boots I’m not going to wear daily, but for tall boots from a well-known comfort brand, I think they’re worth it. They are a bit snug on my calves when worn with thick skinny jeans (I do have bigger calves), but they zip up completely (with jeans) and they fit perfectly with bare legs and tights.

11. Sam Edelman Slouch Boots (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom (Similar On Sale) | At Nordstrom Rack (Most Sizes Sold Out-On Sale)

Pros: I LOVE this style with jeans. LOVE, LOVE, LOVE! They look very on-trend and make a monochrome look pop. These particular ones are sold out, but Sam Edelman has a very similar pair that I link to above.

Cons: Not a comfort brand shoe. They are “comfortable enough”, but no way would I walk in these all day. I’ve worn them out at night and actually did okay dancing in them one evening, but I’m used to (and prefer) a much more padded footbed. Additionally, my feet aren’t very happy when wearing pointy toe shoes, but I caved and kept these for special occasions where I don’t have to walk a ton because they’re so fun.

12. Naturalizer Spotted Heels (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom (On Sale)

Pros: Such a fun print. Love that these are an interesting cool print, but in neutral colors, so easy to pair with lots of other colors or other prints. Supportive and comfortable. Wide sizing available.

Cons: As I mentioned before, I’m not a huge fan of pointy toe shoes (my feet aren’t usually very happy in them), but these are more comfortable than most pointy toes I’ve tried. I did size up to give my toes a bit more room. That being said, I don’t think I could walk in these all day.

13. Naturalizer Green Heels

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom

Pros: Love that these are bold and SUPER high, but because of the platform and Naturalizer design, they’re comfortable (as in REALLY comfortable). I don’t know how they do it, but these are actually walkable and don’t hurt my feet at all. Even though they’re sandal style, I’m still wearing them now for parties/special occasions with fun sparkly tops and jeans. My toes are cold, but whatever…they’re too fabulous to keep in the closet. Wide sizing available.

Cons: They’re high, so they do require some balance to wear them. The thick heel helps, though. I know this chunkier platform look isn’t for everyone, but they have a sleeker green heel, as well as here.

14. Naturalizer Red Heels (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.
We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Macy’s (On Sale)| At Everlane (Similar)

Pros: Comfortable and a great simple style.

Cons: The color is not quite right. It’s a tiny too bright or too orange or something. They’re almost like a neon orange. I like the color of the Everlane ones better that I’ve borrowed from time to time from Shana.

15.  Naturalizer Freya Bootie (On Sale)

We try a LOT of shoes. We research (& wear in real city life) tons of clogs, booties, tall boots & heels for work, travel & party. Here are 15 for this season.

At Nordstrom (On Sale)

Pros: As I’ve mentioned, this year I’ve been so impressed with Naturalizer’s style, and of course, their comfort. These booties have good arch support, and my weight is very evenly distributed when I walk. The double zipper look is cool, and surprisingly comfortable (even though my feet usually don’t like pointy toe toes).

Cons: The leather isn’t particularly gorgeous or butter-soft.

Shop All Stylish Comfort Shoes I Tried
(& A Few More I Want To Try Soon)

As always, PLEASE let me know what other comfort brands you’re wearing and loving. I LOVE to hear which shoes are making other feet happy!

-Linzi

*This is not a sponsored post, but a big thanks to Dr. Scholl’s for sending over some comfy and stylish shoes for me to try. I am always SO happy to try new styles of comfort shoes, am loving your selections, and SO appreciate your dedication to happy feet.

13 COMMENTS

  1. As someone with problem feet, I really appreciate your posts! I’ve bought several shoes based on your recommendations. Gentle Souls and Sofft are consistent brands for me but those Kork-Ease boots were surprisingly comfortable.

  2. Love this roundup, just a small request for next time: could you include “lack of extended sizing” in your cons list, if applicable? Your top two picks (Kork-Ease and Dr Scholls) both start at only a size 6 at Nordstrom, which I know always stocks the full range of available sizes. It would be great for me to know before clicking through and being sad, haha, since I wear a size 5-5.5 (go up in boots, but only to 5.5). Thanks in advance!

    • Ugh. Must be so frustrating Keilexandra. I have a good friend who has size 5 feet, and I’m always so surprised more brands don’t carry her size. I will definitely try to keep that in mind for the future…especially the posts like this one where I go in to more detail. Thanks for the comment.

    • Thank you, Autumn! Jeans are so hard. Not as hard as swimsuits of course, but still hard. I have tried on about a million pairs of jeans this season…I’m struggling with the new silhouettes for sure and whether or not I care if the jeans are “flattering”…one of these days I’ll document the process, but I’ll warn you…it may not be pretty. 🙂 Thank you for the comment-so nice!

  3. The post is interesting. It explores 15 pairs of shoes that you can try this season and presents a comfort shoe follow-up. People enjoy wearing shoes for all seasons. You can buy different shoes for various seasons. However, there is a need to pick the right shoes for every occasion or season. Looking at the post will help you to choose the right shoes for different seasons.

  4. I too am a big fan of Dansko. Most of the boots featured are styled with jeans. I struggle to find boots that style well with work pants. I typically wear Everlane’s Side-Zip Work Pant. Any suggestions?

    • Hi Heather–I’m sorry it took me so long to respond. I got caught up with the excitement of the toy post. Toys and shoes….I’m in heaven responding to all these comments! Have you tried the Everlane day boot? https://shopstyle.it/l/bbWuv I was REALLY surprised by how comfortable they are. I’m usually a give me all the padding, give me all the cushion and arch support possible, but I’ve somehow been able to wear these walking in the city. I think they look great with work pants and they are currently serving as my “dressier bootie.” I see plenty of people wearing Fly Londons with work pants, but you have to like that style (which some folks don’t I know). Do you like the Dansko Raina? https://shopstyle.it/l/bbWv3

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