Soles in the City - A Guide


I'm a city dweller and a city traveler, which means I log at least 5-6 miles on my dogs on normal days, and upwards of 12-15 miles a day when I'm traveling.  

Sadly, I'm also supremely flat-footed and have arthritis in my knees and ankles.  Add an old knee injury sustained in Las Vegas and you've got a hot heeled mess.

In my younger years I'd be quick to sacrifice sensibility over style, but the first tenet of being fashionable is being comfortable in your own skin.   It's hard to be chic when you're hobbling down Fifth Avenue in 5" Stuart Weitzman clogs (Did it.  Wasn't pretty.  Moving on.)

I'm off to NYC in about three weeks (more on that soon) and I'm packing super light for the 3-day trip as I plan to be mobile for most of it. If it can't fit into a medium-sized backpack or a crossbody, then it's not going with.  My general rule of thumb when it comes to packing shoes is this:

1-3 day trip: two pairs, max
4-7 day trip: three pairs, max
7+ days, including special events or occasions and traveling through different climates, up to four pairs of shoes, but you can usually make do with three.

Often times, I'll travel with one pair of shoes (the ones on my feet) for a short trip.  In colder weather, it's almost always a pair of Sam Edelman black booties or saddle brown knee-high Kenneth Cole boots.  In warmer's more of a hassle.  My footwear has got to tick these boxes:

  • Supportive (snug fit, moderate heel for shock absorption)
  • Fits well (not too snug as to where it cuts or blisters)
  • Cushion in the insole 
  • Versatile (I can wear it to a work thing, then sightsee, then go out at night all in the same shoe)
  • Fun

So when you think of comfort shoes, and especially comfort sandals, what comes to mind? Birkies? Toms? Tevas?  (Eww, remember that fashion Teva disaster from last year?  Even Miuccia Prada managed to jump on that bandwagon of ridic.)  I've got some goodies (and some surprises even) to help you avoid veering out of opulent and into orthopedic.

Cool, comfortable, and chic is unbelievably hard to accomplish in a summer shoe, but I have a few candidates.  Check out some of my picks below for a good city shoe that will take you from LaGuardia at 9am to I Love Vinyl in Brooklyn at 10pm.  

  1. Gentle Souls Leah Peep Toe Wedge - I've never been let down by a Kenneth Cole shoe and these are no exception.  The ankle strap offers support and the inner sole is cushioned to help absorb shock while walking.  You could wear this shoe to a business casual meeting and out dancing with no problems.
  2. Gentle Souls Luci Wedge - Again, another Kenneth Cole winner.  These espadrilles are on trend in pewter and have a 1.5" heel that will absorb shock as you walk.  While a little more on the casual side, this is a perfect weekend-in-the-city shoe.
  3. Betsey Johnson Anders Floral sandal - Betsey is the queen of fab and fun with this little number.  Even if your city trip involves time in a suit, you could pull this off as a one-shoe solution to travel by pairing it with a bright eye-catching pantsuit during the day and a flirty skirt for the evening.  The 2" block heel is great for shock absorption and the ankle strap ensure the shoe stays put.  Love these!
  4. Betsey Johnson Abree lace-up sandal - These are a steal and while the heel isn't as high as I'd like (up to 2" for shock absorption), these are definitely on-trend with the tassels and poms and the gold is practically a neutral.  The lace-up styling provides some support around the ankle as well.  
  5. Betsey Johnson Ivee Block-Heel sandal- Betsey is killing it as the queen of cheap and chic with these gingham block heels.  The ankle strap will provide support and this is another choice that can work in a more dressy situation.  
  6. Nanette Lepore Nanette by Dominik Knotted Wedge Flats - Slides are comfy and super on-trend at the moment, although not my first choice in terms of support.  These leather slides will pair up just nicely with all your boho chic looks and could also provide some casual edge to a pair of millennial pink tailored shorts.  The 2" espadrille will definitely provide shock absorption as well.
  7. Mint Bow Flat - Slides are really in this summer and big bows can lend a feminine flair to an otherwise boring shoe.  These are a little flat for my needs, but I recently picked up a similar pair by Chinese laundry that have a little more cushion in the heel.  Bonus:  these are super easy to pack, so you could get away with two pairs of shoes!
  8. Born Havana Slingback Block Heel Sandals -  I would almost never put on a heel this high to carry me around the city, but Born shoes are a notable exception.  Between the thick ankle strap and the cushioned soles, this shoe is capable of taking you from day to night, and beyond.
  9. Birkenstock Linda Slingback - Gone are the days where Birkenstock stood only for comfort with its standard footbed sandals.  The Linda still offers the same support as standard Birkies, but updates the look a bit with some slingback straps.  A good choice for a casual weekend schlepping about town.
  10. Birkenstock Emmy Ribbon-Tie Sandals - Shut the front door!  Super-feminine Birks give you style and substance with the footbed you know and love and ankle support with a ribbon tie.
  11. Dr. Scholls Wynne Strappy Sandal - Want something basic that you know is just going to work?  Here it is in a block heel sandal that will easily go with everything.  
  12. Swedish Hasbeens Mirja Sandal - Instead of trying to run through Times Square in those Stuart Weitzman 5" clogs, opt for some more sensible ones that you'll hold on to forever. With a solid sole and thick ankle straps, you'll come back to these summer after summer.


Honorable mention goes out to Sabahs...I just haven't got my feet into a pair yet! (Mickey Ashmore, I plan to come try them out at the East Village Sabah House.)

What's the good word?  Tell me about your favorite city shoe in the comments!

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