You Pick Wednesday: Cute and Comfortable Shoes

Shopping · You Pick Wednesday

Last week Maggie asked me via Twitter for help finding cute and comfortable shoes. In her words, ballet flats aren’t supportive enough and “good” shoes tend to be ugly.

Well, I suppose that if what you remember are the Aerosoles, Clarks and Naturalizer shoes your grandmother wore then, yes, comfortable shoes are ugly.

But, believe me when I say that shoe brands are starting to get the message. In fact, I bet you can’t guess what brands the shoes below are!

Cute and comfortable shoes


Clockwise from top left: Aerosoles wedges | Aerosoles flats | Clarks flats | Naturalizer flats | Naturalizer wedges | Anne Klein wedges | Sofft flats

I’m personally in love with those leopard print smoking loafers from Clarks. Seriously in love. They also come in other colors but if Zappos wanted to send me a pair (or if a spare $100 fell out of the sky) these are the ones I’d pick.

Overall, I went for shoes that fit my two main criteria for not looking like a frumpy grandmother:

  1. No square toes. Stick with almond, round or even pointed.
  2. No block heels. Unless it’s a wedge, make sure the heel is no more than 1/4 of an inch.

I’ve also heard good things about the Cole Haan Air series but those are pricey. Definitely try on a pair in the store and then look for them online for sure.

Personally, the brand I wear the most is Bandolino but that’s because they fit my wide forefoot and narrow heel the best. Still, I sit at a desk all day so other than the walk to and from the train I don’t necessarily put a lot of mileage on them. Now, though, I have a slightly longer commute so I might be looking for my own pair of cute, comfortable shoes soon!

Do you have any suggestions? Which pair do you like?

To see past You Pick Wednesday Posts, click here.


13 replies on “You Pick Wednesday: Cute and Comfortable Shoes

  1. Dee

    Since my hip replacement my beloved heels have had to go to the back of the closet for awhile. And I agree that “Granny” shoes just don’t cut it. I have discovered ROS HOMMERSON has an amazing selection, very comfortable and stylish. They have about a one inch lift. I know they have saved me from having to revert to “Grannies” for the time being. The heels will reappear eventually.

  2. Allyson

    I was so tired of uncomfortable shoes that I saved up and bought myself a pair of the Cole Haan Airs. Granted I got the heels, but I could not believe how horribly uncomfortable they were! I tried wearing them a couple of times but they were so painful I had to return them. I guess money doesn’t buy happiness in this case 🙂 I think I may have to order a pair of the Naturalizer wedges you posted here. So cute!

    1. Erin @ Loop Looks Post author

      My knee high black heeled boots are Cole Haan Airs and I wouldn’t say they were any more or less comfortable than a non-Air branded pair of boots. But they must work for some people, right??

  3. Bethany @ Accidental Intentions

    They probably don’t fit the dress code for most office wear, but I got a pair of Freewaters flip fops (the Sierras) earlier this summer and I LOVE THEM. They’re a little expensive considering that they’re flip flops ($46), but my oh my are they comfy. They’ve actually been lifesavers with my brush with plantar fasciitis, because they have great arch support. I haven’t worn any other Freewaters shoes, but they do have some really cute options!

    1. Erin @ Loop Looks Post author

      Yeah, that’s a bit casual 🙂 Still, it’s good to know because I’m pretty sure my go-to comfy flip flops are only going to last one more summer before I’ll need to replace them. Now I know what brand to look for.

  4. Maggie

    Thank you! I had a pair of Aerosoles years ago that were super comfortable and I wore alllll the time until they started looking well worn. I’ve been eyeing some cute Naturalizer loafers on Poshmark that I’ll buy once my pending balance goes through. Those leopard loafers are pretty cute, might have to add them to my wish list. Also, my boss has some Cole Haan Air wedges, and she has plantar fasciitis, so I’m guessing they’re comfortable.

      1. Maggie

        I just found those Clark’s loafers in my size on poshmark! Listed for $80, but worth checking to see if anyone listed your size. I also found a pair a half size down.

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