The 14 Most Comfortable Boots That You Can Actually Walk In

And, shockingly, they’re all incredibly chic.

Image from Free People

Image from Free People

by The Candidly Team

We have reached that point in our lives where we are no longer willing to sacrifice our foot comfort to look cute.

WE WILL NOT DO IT.

But. We’re also not willing to wear some matronly, hideous shoes just for the SAKE of comfort.

It’s quite a conundrum, but we feel certain you feel it, too.

So what did we do? We found 14 of the most comfortable boots on earth, that are also very, very chic.

Let’s jump right in. See what we did there?

 

1. The Everyday Bootie

Why we love it: If you’re not on the Kork-Ease train, please jump right on with us. They make the softest, yummiest shoes you’ll ever wear. How are they this cute? We don’t know and we don’t even want to know.

Price: $130


 

2. The Block Heel Boots

Why we love it: The perfect scrunch and length for all your cropped pants and midi skirts. AND you can walk all day in them!

Price: $198


 

3. The All-Weather Leather boots

Why we love it: Every wardrobe needs a solid weather-resistant boot. These just happen to last a lifetime and will be the most comfortable.

Price: $70


 

4. The Walk-All-Day City Boot

Why we love it: The square toe is the hidden secret in why you can walk alllllll say in these boots and never feels squeezed or squished. The only trouble is choosing a color. All 4 are perfect. 

Price: $250


 

5. The Black Leather Booties (That You Can even wear to work)

Why we love it: The butteriest leather. The most walkable heel.

Price: $150


 
 

6. The best wide-calf boot ever made 

Why we love it: BREAKING: These are the only truly excellent, gorgeous, comfortable, wide-calf boots worth discussing. They will actually fit your calves. Yes. We also wept. Plus how chic are they?

Price: $229


 

7. The Classic Chelsea Boot

Why we love it: Yes yes, the price is a bit much. But you will own these boots forever. They’re Frye.

Price: $298


 

8. The Clog Bootie

Why we love it: Yes! Dansko makes cute booties! There’s a reason nurses wear Dansko clogs all. day. long. The foot bed gives gorgeous arch support and these booties are no different.

Price: $130


 

9. The Sleek Suede Bootie

Why we love it: If you’re not yet on the Soludos tip, welcome. The yummiest suede and the most walkable heels.

Price: $149


 

10. the splurge boot that’s worth it

Why we love it: Is this price a leap? It is. But Sarah flint makes shoes and boots like no other (link that word to our 18 most comfort heels round up). They are turkey investment shoes that you will own for a lifetime. And we have never, ever found a more comfortable high heel than hers. Read about the gorgeously precise craftsmanship on her site.

Price: $895


 
 

11. The boot that brings you joy 

Why we love it: When in doubt, wear Hunter. They are like happiness in a boot. 

Price: $120


 

12. The best boots on the list. Sorry. 

Why we love it: These are the boots you’ve been wanting. They just are. They’re the boots we’ll show aliens if/when they come down and ask us what boots are. They’re the boots we’re all collectively dreaming of wearing once the cool snap of fall makes itself known in the air. 

We love these boots so much. They might be our favorite on the list. 

Price: $378


 

13. The Knit Boot

Why we love it: It’s the sleekness for us. (And the unbelievable walkability.)

Price: $130


 

14. The Incredibly Priced, Ultra-Comfortable Wedge Boot

Why we love it: At this price? We’ll take two.

Price: $39

 
 
 

At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
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