Fashion Friday: Comfy Yet Stylish Shoes

My friend Grace (whom I usually call for fashion advice, so let’s band together and solve her fashion dilemma today!) said:

Dear Jo-Lynne Suburban Shopping Star

I love to go into the city – any city – but with that comes lots and lots of walking.  I need comfortable shoes that look good, too.  And I mean comfortable.  Comfortable like Clarks.  But cute with a wedge or kitten heel because I’ve found that just because the shoes are flat doesn’t mean they’re comfortable.

What can I wear when I’m in jeans or khakis doing a day at the museum and dinner in Chinatown?

I say: Ahhh…  Comfort vs. Fashion — the issue that has plagued woman-kind since the beginning of time.  Or, at least, since the invention of stilettos. (And what a glorious invention they were.  Let’s have a moment of silence for the stiletto, shall we?  Okay, moving on.)

Actually, Clarks makes a shoe called Privo that I adore.  I think they are cute and fashionable as well as practical for walking all day.  They work with jeans, khakis, cropped pants, and skirts equally well.

Would something like this interest you at all?


Eh, at second glance, that stripe across the foot is a deal breaker.  That’s too bad; otherwise, they’re cute.

I love these. I’ve had my eye on this pair for about a year. I plan to get some before our Disney trip next fall, although I’m pretty sure they’re not exactly what you’re looking for.


If you want something a little dressier, Me Too makes a very comfortable shoe.  I can see you in something like this.  (It comes in a variety of colors.)


Or this:


You probably want something with a little more SASS, dontcha?

WHEW! It’s not easy to shoe shop for someone else.

What about this?  You simply can’t go wrong with Stu. And they’re on SALE!


Hey, I never said what you’re looking for was gonna come cheap.

If none of these are doing it for ya, let’s meet up at Nordie’s this weekend, and I’m sure we can find something cute and comfy.

What do YOU say? Do you have or know of a comfortable shoe suitable for walking the city streets in style?

Join The Conversation

26 Responses

  1. You are speaking my language this morning. At Christmas, my mom met me at work and we took A to visit Santa at KOP. I had on heels and thought that I was going to die standing in the hour long line. I ran into Nordstrom and bought these in black:


    (Merrill Plie). They are fantastic – I wear them everywhere. Yesterday, I took the train to Center City and wore these on the train and for the walk from 30th Street to my office where I changed into heels.

  2. Steph, I LOVE THOSE! I was in Aldo yesterday and I don’t think I saw those. I love my silver flats from Aldo, but the silver is flaking off. URGH. I would buy another pair, though, just b/c they are so cute and so versatile.

    Megan, those are fun! I would like something like that to throw on with jeans this time of year although I’m still holding out for those Privos I posted.

  3. I totally agree with the Privo suggestion! And I love Me Too shoes–they tend to fit a bit snug on me so I order a half size up. How about Keen’s new style, the Madrid Ballerina? They aren’t as clunky as other Keen styles yet have that wonderfully cushioned Keen footbed. https://www.shoebuy.com/keen-madrid-ballerina/303064/646891

    Also you really can’t go wrong with Born. The Daffodil is such a pretty spring flat https://www.zappos.com/product/7468992/color/11405 and the Sokal is a patent mary jane with cushioned footbed https://www.zappos.com/n/p/p/7412627.html

  4. I absolutely LOVE that first Born in green. WOOOOO!!!

    I think my friend Grace has something a little more pointy/sassy/dressy in mind though. I go for all the cutesy styles, but she’s a little more of the “smart casual” style.

  5. Add to all of the above requirements a shoe that you can buy in a 9 1/2 narrow, and you will solve the bane of my existence. I guess if I knew something would be comfy, I would spend the bucks, but that’s the other problem.

    Seriously. A crisis. I can’t just buy a cute shoe that I see because of the size issue. Forget shopping on sale. Forget cheap trendy shoes. I can’t even find a good pump that is really comfortable.

    Sandals are okay (because they don’t have to “fit” as well), and the same goes for boots, but a regular closed-toe shoe? I haven’t found a shoe I love in years.

  6. I just learned that Crocs makes more than just those ugly beasts you find in the supermarket! They have a super cute ballet flat that I want to try so bad – they look pretty comfy too!

  7. Visiting from big mama because your title said shoes!

    I spent a good part of the evening trying to solve this problem for myself (pregnant with baby #3 and a closet full of high-heels that just aren’t working)

    Here’s what I found:


    and ecco makes comfy shoes:


    and I love Michael Kors – this is great in the fleshtone also:


    It’s so hard to convert to flats from heels!


  8. Bonnie – LOVE the red ones by Ecco. I’ve heard they’re great but never tried them. The michael kors are cute too. Great advice!

  9. I took a further look at your blog – I like it! I’m relatively new to the blogging world, it’s fun and yours is gorgeous. I’ll be visiting again – your topics are a great blend of random and real. My favorite 😉

    By the way, I loved the profile of the Michael Kors shoe – it’s what sold me. Hard to find a flat that doesn’t look like a ski from the side.

  10. Jo-Lynne, Thanks for stopping by today! Great shoe advice! I’m a flats girl myself, so I really like the suggestions you made. I got a pair of silver faux snakeskin flats from White House Black Market that have lasted me for 3 months of good, hard use and they still look great. I walked all over Chicago and NYC in those bad boys! Happy shoe shopping, and best of luck!


  11. I heart my Privos! I wore them at Disney for a week and had not foot pain whatsoever.


    They come in such great colors too – black, white, chocolate, khaki. Plus more than one style so you can keep collecting….

    It kinda sounds like I’m talkin’ myself into another pair :}

  12. Jo-Lynne, I feel like you are my Verizon-like pack of personal shoppers! You are right, I am looking for something more dressy and sassy. I like your Me Toos, but not sure they are really built for comfort? I’m going to try the ECCOs since they seem to emphasize comfort. Nordstrom, here I come! 😉

  13. I love the 2nd pair you have up, but those types of shoes always make my feet look like banana boats. You will have to go shoe shopping with me before I go to Puerto Rico and Disney!

  14. I like the Privo shoes best. The top two.

    The Stuart Weitzman shoes look a little bit “old-ladyish” to me. But maybe that’s just me.

    Your post brought a question to my mind…a slightly embarrassing question, actually…

    I know these type of shoes aren’t meant to be worn with socks. But how do you prevent stinky, sweaty feet…? Tips, please.

    I usually stick with flip-flops and sandals in the summer because I can’t figure out how to let me feet “breath” in closed-toe shoes with no socks. HELP!

  15. Hey Steph. I know what you mean about the Stuarts. I thought Grace might like them, not that she’s old ladyish in the least.

    The sweaty feet thing is a mystery to me too. I guess I just ignore it. Or maybe my feet don’t sweat that badly? I generally wear open shoes in the summer as well.

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