Hi friends! Welcome back to the blog! I hope you’re staying safe and healthy right now during the pandemic.

Recently I’ve been working out at home and I have been trying all of these online workouts to see what I will actually stick with (spoiler alert, I still dislike working out). I decided to do one of my dance videos in the basement and somehow hurt BOTH of my heels. #GettingOlderIsTheWorst

This leads me to try to find the MOST comfortable flats that don’t make me look like an old lady. Let’s be honest y’all, I will totally be rocking comfortable orthopedic shoes when I’m 80, but I’d like to not visit that part of my life yet. So, I rounded up the cutest flats from the companies that claim to be the most comfortable, tried them all, and am writing this post for you with the results.

Style disclaimer: I am completely against open-toed shoes in the workplace. 100% no go. I can sort of handle a peep-toe on occasion, but it’s not appropriate to wear sandals to work. Never ever. (Unless you work at a pool.) When in doubt, look at your executives. If the women wear sandals, your culture supports that. If not, DO NOT DO IT. Unless it’s your name on the door and it’s your own company, you are there to work. I hear allllllll the time from executives and HR professionals who are annoyed by women that think sandals are appropriate for work. They’re not, so stop it.

That all being said, none of my choices are sandals. 😉 Obviously. You might also notice that my beloved Rothy’s aren’t on this list either. Because they are not comfortable enough (padded enough) for actual heel pain. Normal feet? They’re wonderful. Feet in crisis? No.

Here are the contenders (with the price I paid):

Aerosoles East Coast $71
Aerosoles East Side $52
Vionic Mackenzie $40
Naturalizer Lorna $89
Naturalizer Susan $60
Cole Haan Caddie $78
Birdies Starling $140
Dr. Scholls Cypress $45

Aerosoles East Coast

Aerosoles East Coast
Fits true to size. SUPER cute. Minimal cushion. This shoe is adorable and absolutely perfect/unique BUT not enough cushion to fit into the category of a “comfort” shoe. B

Aerosoles East Side

Aerosoles East Side
HOLY MOLY. This is the SOFTEST loafer I have ever put on my foot. The leather feels like butter and the color/shape is incredibly stylish. They come in multiple colors and I would suggest the tan for this fall if you wanted to add a pair to your closet. Wonderful cushion. A+

Vionic Mackenzie

Vionic Mackenzie
The only pediatrist approved shoe on the list and a favorite of Oprah, this shoe is as cute as it is comfortable. The sherpa lining makes it feel like an Ugg slipper, but underneath it packs fantastic arch support and heel cushion. I adore the scalloped detailing too! A+

Naturalizer Lorna

Naturalizer Lorna
This shoe was super cute, but for $89 it wasn’t worth it to me. It’s SUPER cute, and I loved it in white, but it wasn’t heavily padded in the heel and so it went into the “no” pile. It scores a B.

Naturalizer Susan

Naturalizer Susan
This was the biggest surprise for me. Not only is it insanely comfortable, but I get SO many compliments when I wear them! They’re a sneaker/ballet flat/wedge hybrid and they’re lovely! The back of the heel is padded so it doesn’t rip up your Achilles. SO GREAT. (They also come in other colors!) A+

Cole Haan Caddie

Cole Haan Caddie
I allllllmost kept this one. It was really quite comfortable, but at the end of the day it didn’t feel worth the price. I know $78 isn’t a lot compared to others, but since I wanted multiple pairs, it wasn’t worth it. I like the bow/knot detailing! B-

Birdies Starling

Birdies Starling $140
So here’s the surprising thing. I put them on and immediately said “nope!” and promptly took them off. They were a tiny bit too small and I knew that I would have to spend a lot of time breaking them in. Spoiler alert, I don’t really believe in “breaking shoes in.” If they aren’t comfortable, don’t buy them. They were insanely comfortable in the footbed though, so if you like the style, I think they’re worth the money. I just didn’t want to spend $140 on shoes I had to break in that were also limited to the spring/summer. A-

Dr. Scholls Cypress

Dr. Scholls Cypress $45
My reaction was “Dr. Scholls makes shoes??” Haha, apparently they do and they’re also quite comfortable! They even made the heel out of stretchy material so it doesn’t cut into your foot. I love the grey color, but I’m not sold on the material. It feels a bit cheap. Although for $45, they’re a fantastic shoe. B+

Dr. Scholls Cypress

I know there are MANY other brands of shoes that I may have missed, so if you have a favorite that I left out, please leave them in the comments below! Hopefully, this has helped give you some clarity if you’re in need of a new pair of work shoes. I still love my favorite ballet flats of all time and those are still in the rotation!

Until next time!

If you liked this post check out my review of Rothy’s, Tieks, or designer heels!

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Adriele