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How to Find Stylish and Comfortable Shoes

By Amalah

Dear Amy,
Long-time reader, first-time questioner here.
Recently, with the gas prices and the environment and whatever else I should care about, I started taking mass transit to and from work. This requires me either to walk from my house to the bus stop or (if I ride with my boyfriend to the metro station) from the car to the metro station. In either case, this is a little less than half a mile. Then its metro to the bus to work and then another half a mile from the bus stop to my office. So, I’m walking almost a mile before I even get to work and then repeating this in the afternoons.
I refuse to follow suit of the middle-aged suburbanites who wear their stark white sneakers and socks with their dresses, but I completely understand why they do it and envy their lack of fashion sense. I have been wearing pink flip flops as my commuter shoes and then packing the office shoes in my briefcase, but even the flip flops are starting to become uncomfortable.
What I’m looking for is a cute pair of commuter shoes that will not kill my feet. I would especially be pleased with shoes that I could wear all day, but I don’t want to ask for too much. Any suggestions?

On my recent fashion scouting expedition to New York City (also known under the decoy code name of Jason’s Birthday Weekend), I spent a lot of time checking out all the hot tail (also known as Seeing What the Stylish Pretty People Are Wearing These Days). I was converted to the minidress-over-jeans look (my apologies to the Fug Girls) (I’m also on a mission to find a cute pair of dressy shorts) and I also realized that flat shoes can be really, really cute.
Everybody was wearing flats. Or flip-flops, but it was mostly the super-cute flats that caught my eye. Cute! Practical! And at least giving off the illusion of being comfortable!
Of course, I’ve since tried on quite a few pairs that were anything but comfortable. Usually these were the super-cheap ones stamped with ALL MAN-MADE MATERIALS on the sole, so I shouldn’t have been surprised. The same shoe rules apply to even the most ballet-slipper-like flat: Be kind to your feet. Don’t encase them in plastic-y pleather and cheap pinchy shoes with unfinished seams that rub. A lot of flats also have ZERO arch support, which is the same reason your flip-flops are hurting your feet. (Also! Exposing all the skin of your feet to the air all the time will cause cracks and dryness. You might as well be going barefoot.)
So! Onward! To the freaking point! POST SOME SHOES ALREADY!
Here are some flats that I think would be perfectly acceptable to wear all day at work, and also (hopefully) make your commute more pleasant. (I can’t really tell how great some of these are arch-support-wise, but that is why God created the Zappo’s free return shipping policy.
dansko.jpgOkay, this first one may make your Manolo-sense recoil a little, but bear with me: the Dansko Mary-Jane flat. So yeah, they are not the cutest little twee shoe in the world. But they are comfortable. They are good for your feet. They are also…not half bad. I love the strap and I can totally see the black ones looking pretty darn cute with a pleated skirt or some dressy cropped pants.
For a more stylish take on the same idea, these patent-leather ballet flats (patent is sooooo hott right now) from BCBG sound pretty comfortable, although I’d probably look into replacing the “foam insert” with something a little more substantial by Dr. Scholl’s.
bcbgshoes.jpgThat same tactic might work with pretty much any of the ballet flats. And here Zappo’s selection is positively mind-blowing, so it all comes down to what personally appeals to you. 1,844 pairs of ballet flats!
Brands built for comfort (besides Dansko) include Born, Ecco, Clarks and Rockport. Brands built for style (but are still decently comfortable and excellent quality) include Delmans, Donald J Pliner and Stuart Weitzman. Brands (in my own experience) that tend to look way better than they feel are Steve Madden and Nine West. It’s all about what you’re willing to spend and what the rest of your wardrobe looks like. (I could sit here all day linking to cute black shoes and all you wear are earthtones.)
So! To recap! Flats! Real leather! Go for ultra-comfort if you are okay with still packing a pair of heels in your bag, and go for additional arch support in an otherwise well-fitting shoe if you aren’t. Either option is worlds better than the office-attire-with-sneakers look, but then again, this is coming from someone who no longer thinks dresses always look ridiculous over jeans, so clearly I have lost my damn mind.

About the Author

Amy Corbett Storch


Amalah is a pseudonym of Amy Corbett Storch. She is the author of the Advice Smackdown and Bounce Back. You can follow Amy’s daily mothering adventures at Ama...

Amalah is a pseudonym of Amy Corbett Storch. She is the author of the Advice Smackdown and Bounce Back. You can follow Amy’s daily mothering adventures at Amalah. Also, it’s pronounced AIM-ah-lah.

If there is a question you would like answered on the Advice Smackdown, please submit it to

Amy also documented her second pregnancy (with Ezra) in our wildly popular Weekly Pregnancy Calendar, Zero to Forty.

Amy is mother to rising first-grader Noah, preschooler Ezra, and toddler Ike.

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  • Giada

    June 29, 2007 at 11:38 am

    I’d definitely recommend the ballet flats. I bought a pair from Nine West about 4 years ago. (I’m SUCH the trend spotter. Ok, not really — they were pink and cute and on sale.) It took a while to break them in, but now they’re extremely comfy and still adorable. I’d recommend getting some inserts though, as ballet shoes tend not to be so great with arch support. Ballet flats are also great when your expensive jeans shrink and become too short for heels, but yet you still want to wear them with something cute and trendy.

  • Valerie

    June 29, 2007 at 12:00 pm

    Thanks so much! Since everyone’s pretty much out of the office today, I’ll be spending the rest of the afternoon looking at Zappos and finding a few hundred pair of shoes. Yay!

  • Melissa

    June 29, 2007 at 12:27 pm

    Dansko has some other cuter, less heavy styles such as the Madrigal and Suzette. I have the Marcelle and they are quite comfortable.
    I broke my ankle quite badly a little over a year ago. Metal plate+screws+high heels=PAIN. So I mostly wear flats.

  • Vida

    June 29, 2007 at 3:41 pm

    I just bought a pair of Kenneth Coles from DSW (I love that store more than words could ever express). They’re wee little Mary-Janeish flats that go with EVERYTHING (jeans, skirt, dress pants, etc). I can even wear them with or without socks, and they’re still comfortable. It did take a couple days to break them in, but now they’re my favorite shoes. This is saying a lot since I have bunion-like things on my feet that make almost everything but flip flops really uncomfortable.
    I was going to put up a link to a picture, but I can’t find a picture now. Yeargh.

  • Stephanie

    June 29, 2007 at 5:11 pm

    Oooh… I totally asked this same question a couple of months ago when you had that sort of free-for-all day in the comments. One of your readers (sorry, I don’t remember her name!) suggested the Skechers mary-jane flat type sneaker-shoes like these – (There are a million different variations on Zappos.) I haven’t bought any yet, because once it gets warm enough I just wear my Reef flipflops to and from work (for me, they have enough arch support once broken in, since they sort of mold to your feet), but I will probably by a pair once the weather gets colder again. I just keep all my work shoes in my file drawer at work (that’s what it’s there for, right?). I’ve also found that my Kenneth Cole heels are fabulous, and while I wouldn’t wear three inch heels on my hike to and from work, they feel great all day in the office. I may look into getting a lower heeled pair or a pair of their flats when it gets cooler, so I don’t have to do the whole shoe-change thing.

  • mommastantrum

    June 30, 2007 at 12:30 pm

    I LOVE LOVE LOVE the Merrel Mary Janeish Plaza Bandeau. This suede shoe has a slight heel but has AMAZING insole support and feels like you are barefoot, but better. They are great for dress or slacking. (Mostly here chasing a three year old maniac.) I have 3 pairs in a variety of colors to match my mood. They are about $89 a pair at Nordstrom, but I am sure if you are not a slacker like me you can find them for less elsewhere. I honestly never travel without these shoes, and tell everyone to buy at least one pair. And never ever have I gotten more compliments on shoes that are so basic and comfy!!

  • madmjay

    July 1, 2007 at 1:07 am

    If you are looking for simple, comfortable, affordable ballet flats (with no buttons, bows, studs, or any other b.s. adornments) check out the “Afar” pair at (they are the last shoes on the last page in the “shoes” menu. I have a pair in black and another pair in gold. My friend has brown and a really pretty raspberry satin pair. They are $19.99 (got them at a discount shoe store in Houston called Shoe Cents–PROPS!) and I’ll keep buying more. They quicky mold to your foot, the inside lining is soft and “suede-y” and they look cute with EVERYTHING! The only bad thing I can say is that you may want to get a thin arch support if you have high arches. Rocketdog ( also has some really cute Asian inspired flats called “Rattle” (in black or red) that I am currently coveting. Hope that helps and happy discount shopping!

  • Tara

    July 2, 2007 at 10:47 am

    As much as I love the look of not-sneakers for the commute, the practical side of me says if the unthinkable should happen and Metro is unable to get out of town, I can at least walk home in my sneakers. Fashionista, be damned, when it comes to getting home safe and without aching feet.

  • Isabel

    July 3, 2007 at 1:52 pm

    I bought my first pair of flats last month and was totally surprised at how uncomfortable they were. I hate them. But I wear them because, hello, cute!
    It hasn’t been said yet, but Aerosoles are so comfy and you can find decent looking ones. And their sales are to die for.
    (I recently bought my first pair of decent flip-flops based on another Smackdown post. They have changed my world. Hello arch support, where have you been? Gone is my commute home in 3 inch heels.)

  • Kathleen

    July 3, 2007 at 5:18 pm

    I have the same issue, plus I have to hike up a humongous hill from the bus to work (and then, of course, hike back DOWN it in the evenings).
    I got these about three months ago at Shoe Pavilion for $45, and I LOVE them.They work with pants, with skirts, and with capris. Plus, they are super comfy. I highly recommend them! It took me forever to find these, which are both comfortable to walk in as well as work appropriate.

  • Sunny

    July 4, 2007 at 12:30 am

    As someone who’s got hair on the dry-thick end of the spectrum, does anyone have any reccomendations? I’ve tried (and liked) Dove, am currently using Suave Prof, and wondering if there’s something out there in the way of hope for those of us whose hair weighs a ton and frizzes occasionally.

  • Syko

    July 5, 2007 at 11:11 am

    I have antique feet with a BUNCH of problems – metatarsalgia, bunions, etc. – and almost all shoes hurt. I also do not keep a vehicle and rely solely on public transit. There is a company called FootSmart that has all kinds of really comfortable shoes, designed to deal with all sorts of problems, and they look good too. You can find them online at or they will send you a catalog. You can even search their site by your problem. I got some great shoes from ProPet that look like loafers and feel like house slippers.

  • Jessica Rosenberg

    July 5, 2007 at 5:43 pm

    Personally I’m addicted to Rocket Dog shoes. They have so many cute flats this summer and they are so comfortable!

  • foodmomiac

    July 7, 2007 at 8:53 am

    Commenting late, but…
    I wear flats almost every day. The most comfortable are my Clarks Privo:
    Those are really more of a Friday shoe, though.
    I also love anything BC:
    These are like sneakers, but not!
    Oh, and Berne Mev are always super comfortable, and Zappos really needs to start carrying them.

  • ais3

    July 10, 2007 at 1:19 pm

    First time commenter, long-time amalah/dcfoodies reader. A little late, but still:
    MOST COMFORTABLE SHOES THAT AREN’T UGLY of recent purchase are peep toe flats from the Gap outlet which are stylish, cute, but super comfortable–I even wore them walking around town in the intense DC heat, and the hot/sticky/rubbing-against-theshoe thing still didn’t induce any blisters or pain, because the part around the toes are made of soooft material. Very happy. I have other flats that cannot stand up to this kind of activity–comfortably. I have said flats in tan, but they had black.

  • scootnshoot

    July 10, 2007 at 4:03 pm

    I really like Earth brand shoes. You can find them online pretty easily. They’re a little distinct looking, but they are really comfortable. They have good support, unlike the BC and Rocket Dog flats that have been suggested. Earth isn’t as fashionable or adorable as those two brands, but they hold up great and give your foot the support it needs.

  • Emily

    October 27, 2008 at 11:57 pm

    I have a pair of those BCBG Celena patent flats. They’re comfortable for short distance walking, but if you’re doing a lot of walking around the mall or casual strolling for recreation- these can get uncomfortable really quickly. The padding is very flimsy; there’s virtually no support in the insole. I have a heel spur (from walking on hard surfaces because of these shoes, my heel hits the pavement at a greater force with these shoes than any other shoe) and have to see a podiatrist now because of these flats.