My Never-Ending Quest for Seriously Comfortable Summer Shoes

(Graphic: Helen Jane Hearn/

“Size 10 and a half if you have ‘em?”

I handed two shoes to the sales person — a sleek silver oxford and a squishy-souled FitFlop sandal. Comfy shoes.

I looked just across the crowded Lord & Taylor shoe department to see a crisply-habit-ed nun, legs crossed demurely, waiting for something or someone. She smiled at me.

(I was working on the Faith issue at the time, so of course I took this as some prescient moment. Anyway. )

When the shoes arrived, the silver oxfords were a bust: beautiful but ouch-tight and narrow. At this point in my life, I simply can’t wear anything that remotely hurts.

Wrenching them off, I slipped on the FitFlop. Thick black straps, a cork sole — they weren’t the belle of the ball but they promised podiatric pleasure.

tuenight shoes comfort style go out sandal
(Photo: Courtesy of

GLORY BE if they weren’t the most comfortable objects I’d ever slipped on my feet. Like walking on air. No, as if I simply didn’t have feet — just fluffy clouds attached to my legs.

They didn’t look half bad with my cropped jeans, did they? I shifted from side to side in the mirror.

The nun appeared to be trying to get my attention. When I looked over at her, she flashed me a thumbs up, nodding her head.

God approved.

And I cringed a little.


At one time, maybe 20 years ago, I could wear the pointiest of kitten heels or the grooviest of stack-heeled mod boots, but in the last decade, I’ve left fashion behind in favor of flats, oxfords, sneakers, no-more-than ½-inch heel boots and sandals.

Clearly I’m not alone, and it appears the sensible a.k.a. “ugly shoe” has become chic.

Those sandals an ex once called “birth-control shoes,” Birkenstocks, have become a fashion staple, per a recent article in The Wall Street Journal (note, this is The Wall Street Journal), as have clogs, the podiatrist-designed Worishofer sling-backs, “flatforms” and thick-soled sandals from the likes of Miu Miu and Stella McCartney.

I couldn’t be happier.

As someone with bad knees and — oh feet are so gross — occasional plantar fasciitis, a bunion, hammer toes and whatever else, one hour in a pair of simple pumps can ruin me for weeks. The Net-a-Porter array of dagger heels are never, ever going to be in my shopping cart (or budget).

So in my quest to find the most comfortable shoes — other than, well, sneakers — I’ve been charting a few of the coziest, affordable styles that still have at least an ounce of flair. Some of the shoes touted as comfort are basically a flat slab of wood or feature a pointy toed D’Orsay that’s a recipe for a future bunion. And sure they feel ok in the store but try walking in them for more than 20 minutes.

So here we go.

Please, PLEASE share your own tips — did you see that title “never-ending quest?”

Cole Haan Oxfords, $198-248
I own both Gramercy Oxford and the Lunargrand; the Cole Haan oxfords are clearly popular because they keep inventing new varieties. They even have breathable, summery styles. Versatile, chic, and offer plenty of support. I’m a fan of the metallics which go with everything.

TueNight Shoes Cole Haan Comfort Go Out Style Fashion
Me in my shiny Cole Hann’s (Photo: Courtesy of Margit Detweiler/

Ja-Vie Flats, $68
In the world of foldable flats, there are Tieks, numerous other brands and then there is the start-up Ja-Vie. I’ve written about these fab flats before. They’re not ideal for a long trek, but perfect for a party or a day at work. They’ve got better shock absorbers than some of the other brands — and still fit in your purse.

TueNight Shoes Ja-Vie Flats Fashion Comfort Go Out Style
(Photo: Courtesy of

Fit Flops, $100
As previously mentioned, FitFlops appear to be ramping up their chic factor. After spotting the Lord & Taylor jobbies, I just saw these and may have to plunk down some cash.

tuenight shoes go out style fashion comfort sandal
(Photo: Courtesy of

Eileen Fisher Sport Sandals, $195
Pair these flattering platform sandals with an all-black get-up and you’re sleek and set for the day.

TueNight Shoes Eileen Fisher Comfort Fashion Go Out Style sandal
(Photo: Courtesy of

SixtySeven Annie Sandals, $68

Super cute and the cork footbed molds to your foot, so you know they’ve got it going on. Bound to go with everything this summer.

TueNight Shoes Sixty Seven Annie Fashion Comfort Go Out Style sandal
(Photo: Courtesy of

Pikolinos Massai Project Sandals, $180-$250
These extremely well-made shoes are head-turners and with a bit of an arch, feel great on your feet. You can walk around in these for miles. The beaded part is made by the Massai tribe in Africa; the leather in Spain.

TueNight Shoes Pikolions Maasai Fashion Comfort Go Out Style sandal
(Photo: Courtesy of

Thierry Rabotin Flats, $430
Not the chicest, a hair dowdy and pricey — so why are they on this list? Because these shoes kind of saved my life. Amazing if you have bunions, I bought these at TipTop Shoes in Manhattan, which is filled with old school salespeople that measure your foot, talk to you about your “problems” and then find you the perfect shoe. The salesguy at TipTop explained that these have a roomy toe box, arch support and come up a bit high on the toe cleavage which is more supportive (though not as sexy). I just needed a basic black flat and these have lasted me almost four years — and I’ve worn these to death.

TueNight Shoes Tip Top Shoes Fashion Comfort Go Out Style
(Photo: Courtesy of

ToeSox Serenas, $42
I know. They are, as one says, fugly? However, the comfort level is off the charts. I just learned about these from my yoga teacher who recommended these toe-spreaders as a great solve for bunions. And they’re made out of yoga mat material which is kind of genius. They don’t look as bad on. Promise. Yogi said she walked all over Europe in them. Not something I think I’d do, but interesting tidbit.

tuenight shoes go out style fashion comfort sandal
(Photo: Courtesy of

Crocs Rio, $50
Seriously. Yes, my podiatrist gave me a discount but these plastic things are washable, breathable and adorable.

TueNight Shoes Style Go Out Fashion Comfort Crocs
(Photo: Courtesy of


So, I bought the FitFlops and left the oxfords behind. My rule is new shoes must feel nothing short of perfect. I know to leave even a bit of agony in the shoebox.

After exiting the store, I was desperate to get these bad boys on my feet. So, sitting on a bench in Bryant Park, I ripped off the tags, threw out the box and slipped them on. Ahh, salvation.

Maybe that nun was right after all.

When I brought those Fitflops home, my husband recoiled, “German tourist!” he pointed at my feet. I boldly strutted past him.”Whatever, they’re the in thing now,” I informed him, “and they feel amazing.”

Eyes may be the windows to the soul but your soul is in your sole.

So, you know, don’t squash your soul.

Tell Us in the Comments

What do you think?

4 Responses

  1. Elena

    Margit: I am a 10.5 too. It is a tough size! I love in Ecco shoes because Italian sizing has a 10.5 equivalent (41?) I have their little flats in every color. And I wore the stretchy black shoes all over Italy and Israel…with jeans, dresses, etc. I highly recommend them.

  2. Ellen

    You would only be labelled a German tourist if you wore socks with those sandals. I assume the picture at the top was just in jest? 😉

    I am also on a never-ending quest for the right shoes and I feel your pain (both figuratively and literally) about buying anything that isn’t comfortable. I spend more time walking around in a potential new pair at the store than anyone I know. Then usually leave empty-handed because it didn’t pass the test.

  3. Julie Parr
    Julie Parr

    I had been admiring those Eileen Fisher sandals for some time now, and this article pushed me over the top. I ordered them. V. excited.

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