My very first summer in Chicago has been nothing short of glorious. Clear blue skies, bright sunshine, and a city ripe for the exploring. Who could ask for more?

Well for someone like myself with super flat feet and the sometimes-painful issues that go with that, I’d have to admit that a pair of comfortable yet cute shoes would be nice.

This summer I’ve done a LOT of walking around the city, and I’ve had to try out several different kinds of shoes before I found that perfect combination of both cute and comfortable. So without further ado, here are my top shoes of the summer, in no particular order.

Birkenstock Madrid. I think Birkenstock gets a tarnished name among snooty types who like to get on their high horses about fashion. The brand is beloved by hippies and outdoorsy types for a reason – they are durable and comfortable, and you can walk for a long time in these shoes without feeling the pain. The Madrid sandals follow the shape of the original, and promises to tone your foot and calf muscles while improving circulation. That means these shoes take have some getting used to, but I’m a fan of the fit, the look, and the range of colors! These aren’t grungy hippie sandals sold only in earth tones, y’all. Birkenstock has stepped up their game and these sandals are available in everything from black patent to bright citrus yellow. I was sent a pair of the Onyx color and I LOVE it – its a slightly shimmer pewter. Not boring, not grungy. I’ve worn these to concerts, to the park, just going shopping on a weekend with jeans or long skirts – even the right minidress. Cute, comfortable…love em.

Chinese Laundry flats. I’ve been an admirer of Chinese Laundry for a while and I’ve bought several pairs of their shoes over the years. But only recently did I discover, which can best be described as shopping crack. I can’t stay OFF this site. They have frequent, deeply percentaged sales on top brands. So thanks to my addiction to, yours truly was able to get a super cute pair of Chinese Laundry flats for $10. I didn’t realize at the time that they would turn out to be the most comfortable flats EVER. Not the cutest photo and I don’t know the name of these even…but if you see these for sale at your local TJ Maxx, Marshalls, whatever – try them and then buy them, cause they rock!

Puma ballerina flats. For years my best friend Jenny was telling me, girl get yourself some Puma flats. See, Jenny lives in New York City and walks EVERYWHERE. So while we may not share the same feet issues, she knows how important a pair of cute, comfy flats can be. Puma ballerina flats are light, flexible, and sporty-chic. I own a pair that has an adorable ruffle near the toe and I get compliments whenever I wear them! I’ve currently got my eye on the Saba Sequins ballerina – they’re sporty yet dressy and look super comfy! (I’m waiting for them to pop up on!)

My quest for the perfect comfortable shoe will continue into other seasons, but these were my top picks of the summer and I’ve been practically living in these shoes. What are your summer shoe favorites? Share with me!

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Mo says:
August 27, 2010, 10:29 am
thanks for sharing! i need to retire my comfy summer flats as they're starting to look quite worn =( guuurrrrlll every time i log onto 6pm i feel like a hype smacking veins preparing for the needle AAAWWWW LAWD!
SweetThang says:
August 27, 2010, 11:11 am
The Puma flats are cute. I like to get a pair of those for myself. These shoes don't gush or spread out do they? The gushing is a problem with flat feet. I feel you on the flat feet. I have flat feet, too. I wish I was one of those women who can wear high heels but no such luck.
Dasheen Magazine says:
August 27, 2010, 12:43 pm
Bella, My summer shoes were a wedged animal print from Target(I think Exhileration?), a gold jelly pair of gladiators from Old Navy and a goldish/pewter thong sandal also from Old Navy. Talk about heavy rotation! I'm thankful to be in year round sun (for the most part) cause I can't let go. Oh and pass the pipe please on 6pm. I'm in trouble again lol Thanks for posting.
Reecie says:
August 27, 2010, 1:19 pm
I like the Puma flats also. I have flat feet as well, and my podiatrist actually prescribed Birkenstocks to me years ago--of course I never purchased them *hangs head* because I thought they were ugly and cost too much! I will have to hunt for some of the updated versions.
sandra says:
August 27, 2010, 2:02 pm
I feel you on flat feet. I have longer toes and I tried so hard to wear the birkenstocks but my toes kept going over the flat ridge around the edge and it hurts. I can't wait to hear from other bellas on the sandals thing. I just bought some by a company called NAOT: they are extremely comfy but you have to find the style that fits with your wardrobe. I've had three pairs of NAOTs and they were so comfortable they became house shoes before street shoes. With bad feet it's sometimes hard to look cute. Bella I can't remember but did you do a favorite post concerning spanx vs. other brands for formfitting garments? if not, I'd love one of these posts. Thank you.
BlackBetty says:
August 27, 2010, 3:48 pm
I hate shopping for shoes because almost every pair hurts. Or they start off nice and comfy and then have me limping. Not a good look. I've been wearing a pair of silver sandles from Frye that I found at TJMaxx. Also a pair of slip on purple converse sneakers. They aren't that comfy but they look adorable with a skirt.
juliette says:
August 30, 2010, 3:49 pm
THE SHOE THING! The ongoing challenge of finding an appropriate selection of comfortable yet cute/professional/sexy shoes (separately or all at once) is ongoing. My feet aren't quite flat, but I have back problems. So I have a large wardrobe of 3, 4 and 5 hour shoes. I would love to find a pair of 3 inch, pointy toed heels that I could wear for more than 3 hours with limited walking.


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