It’s Official: These Are the Most Comfortable Shoes of All Time

I’ve tried them all and only these meet my exacting standards.

This post may contain affiliate links, which means we may receive a commission if you purchase through our links. Please read our full disclosure here.

We tried them all and these are the best. List of the most comfortable shoes of all time

Picture this: You are walking down the aisles of your favorite store, scanning the shelves for that perfect pair of pumps. Minute after minute goes by until you *finally* land your eyes on them. You can’t wait to try them on. You slip your feet into them, and — of course — your soles immediately cramp up. Another shoe, another disappointment.

And those sneakers that are *all the rage* right now? Yeah, they give you blisters every time you put them on.

I hear you, girlfriend; I have had both of these experiences and more. The truth of the matter is, many stylish shoes kill your feet. And, sure, you can put up with a bit of foot cramping and a couple blisters for awhile, but there comes a time when you must put your foot down (literally) and say enough is enough. 

That’s why I recently embarked upon on a quest to find shoes that are both cute and comfortable. Every girl needs at least one pair of ultra-comfortable shoes in her wardrobe. And I’m here to help you find them.

I have compiled a list of 8 pairs of shoes that, from my experience, have merited the title of Most Comfortable Shoes of All Time (and they’re cute to boot!). Drum roll please…

We tried them: These are the most comfortable shoes for women of all time, including Chacos sandals, Birkenstocks, Steve Madden quilted slip-ons, Converse sneakers, slingback heels, Toms slip ons
Shoes: 1, 2, 3, 4, 5, 6, 7, 8

Note: Most of these shoes are a tad expensive (over $50). Unfortunately, sometimes you have to pay for comfort. Though these picks will require a little extra cash, I highly recommend giving them a chance if you are looking for a shoe that is both cute and comfy.

1. Chacos

Ahh, Chacos. The sandals that are often talked about in backpacking/outdoorsy circles (but they’ve made it to CF before!). Well, all the hype is well-founded! I wore my pair of Chaco’s every day when I went to Europe — a 24 day excursion. By the end, my feet were in ship-shape! These sandals definitely have the comfort factor down, but they also come in a plethora of colors and styles to best suit your needs. 

2. Steve Madden Slip-Ons

Steve Madden is such a trustworthy brand — I had no trouble fitting one of their shoes in my list. These quilted slip-ons have padding on the inside to ensure a pillow-like atmosphere. They’re both sporty and soft-looking with their blush exterior. The only qualm I have with this shoe is it seems to run a bit small, so make sure to go up a size! 

3. Converse Low Tops

Well, according to Seventeen Magazine, Converse holds the banner of being the most popular shoe brand in the US, and I, for one, am not surprised. Converse have been the cool-kid shoe since middle school and it’s easy to see why. Converse All-Stars are comfortable, simple, and so versatile that they can go with almost any outfit you pair them with. Yes please.

4. Birkenstocks

Cool, effortless, adaptable to your feet…good ‘ol Birkenstocks. Forever a CF favorite, these sandals are perfect for the lady on the go — I have a friend who wears them every day and walks everywhere in the big city she lives in. The material they’re made with is very durable (which is why they’re a tad expensive). One of the best things about Birk’s, though, is their adaptability. All shoes have a breaking-in period, but Birk’s reform themselves to your feet, ensuring a perfect fit that lasts. 

5. J.Renee Pumps

Not all heels have to hurt your feet! These J.Renee pumps from Amazon are the perfect combo of comfy and cute: They boast a soft insole, a flexible outsole, and a myriad of colors to choose from. The footbed is also covered with memory foam to make sure your feet are comfy and well taken care of. Also, the heels aren’t too high, so you don’t have to worry about toppling over, either! 

6. Toms

Okay, okay, I cannot rave enough about these flippin’ shoes: Toms are my favorite shoes in the whole wide world. There are styles upon styles to choose from, they match with every outfit (especially if you buy a neutral color), and they are so comfortable. I wear mine constantly — they started out an ivory color and now they’re pretty grey, but they’re just as comfy! They are the epitome of slip-on shoes: no effort is necessary because the elastic “v” in the front of the shoe ensure an easy-on, easy-off type experience. These are another shoe that mold to your feet, as well. Long story short: these shoes are the real deal.

7. Adidas Sneakers

I had always been a Nike girl until I heard about these Adidas sneakers — they’re called “Cloudfoam” for a reason. These shoes are incredibly breathable and flexible, making your feet feel like you’re, well, walking on clouds. They are also very lightweight, making your *running around doing errands* day easier. Sign me up.

8. Aerosoles Booties

For my final shoe recommendation, I present you with Aerosoles’ booties. These ankle boots (or “shooties”, as some call them) are the perfect addition to any lady’s wardrobe — sleek, stylish, and, of course, comfortable. These boots boast a double padded memory foam insole, and the leather look adds a perfect flair to an otherwise drab outfit. Check, check, and check. 

Ta-Da! What do you think?

What are your thoughts on my list of the most comfortable shoes of all time? Do you have any additions to the list? Which of these do you have and which would you like to try? Start the convo in the comment section below.

Leave a Comment