Dear Maggie,

Shoes confuse me. I dress casually, think long sweaters and tunics with leggings. In the winter, I often wear long boots. But in the summer and in between months, it's hard to know what to choose. I've had several hip surgeries so I have to stick with flats and I need arch support. Most flats are flimsy. But I don't want to look like I wear orthopedic shoes! Suggestions? Brands that you like?

Abby, Jersey City, New Jersey

Dear Abby,

It is hard to find a good pair of shoes that are supportive and don't look like your grandmother's shoe selection post bunion surgery but they DO exist!

Though I do not have the same medical problems as you (hope your hips have healed!) I do walk a lot in NYC and have found that if I do not have a pair of supportive flats I am in extreme pain by the end of the day--and they wear out really fast. (Twice I've worn out a pair of cheaper shoes within two weeks of purchasing them.) My go-to shoes this summer were a pair of Clark's black leather pointy-toed flats. They were classic and got me everywhere. Even my friend's kids could not resist trying them on they were so appealing! :) I wore a hole in the sole by September and my favorite shoe dude repaired them like new. I can still be spotted running down Broadway in them, Venti-black iced tea extra ice in-hand.

Here is what I look for in a pair of flats:

Style. I'm with you, Abby, I do not want to look like I'm wearing orthopedic shoes either.
Sole. If the sole looks like it can take a beating, i.e. a little thicker than the usual flat, I am more likely to purchase. Especially if they are rated highly for arch support.
Will I wear them next season? I try to only purchase items that I like enough to wear more than one season. I also buy things that are made well and I know can be repaired if worn a lot. (i.e. those Clark's flats).

Clark's is my personal go-to brand, but I wanted to offer more options, so after reading lots and lots of reviews on Nordstrom's site I put together a Pinterest board for you: Comfortable Flats. I chose the pairs that I thought were the loveliest and that had the highest rating for arch support and comfort.

Dear Readers, what brands do you like? Did I miss any? Please share in the comments!

With love,

Maggie

PS Send in those questions! Holidays are coming up, I'm sure you have 1000 questions you'd like answered, and I'm here to help!

PPS These opinions on Clark's and Nordstrom are my own. I am not being compensated to give them a shout out.