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?