18 Seriously Comfortable Shoes for Spring and Summer

By Margit Detweiler

My shoe predicament has become even worse.

About two springs ago, when I was on the hunt for the bestest, comfiest, maybe even cute-in-a-certain-light pair of shoes, I wrote this piece and was pretty proud of myself for rounding up such stellar soles.

Over this past winter, however, I’ve realized that I’ve become so picky and obsessed with cushion and easy-to-wears that I’m down to TWO — count ‘em, just TWO — pairs of shoes: These perfect comfort-and-support sneakers from Asics (The GT-2000 4) and these vaguely chic, utilitarian suede boots from La Canadienne (The Felicia). I toggle back and forth between the pair. I blame some of my choosiness on going through some big physical ordeals this past year or so that made me ONLY do what feels good and right. Anything that rubbed, pinched, pressed or made me hobble around was so far from ok that I would ONLY wear shoes that felt like heaven.

Now that it’s springtime and the sun wants to shine on my toes, I need to expand my range. I can’t hide in delightfully smushy heeled boots.

After a bit of research, trial, error and crowd-sourced recommendations from friends and colleagues, here are several shoes to break me out of my rut with a few updates to comfy classics. (That’s you, Birks.) I can’t vouch for all of them, but this should get you started on your own well-heeled journey. Ample toe box FTW.

Sneaks

1. Allbirds Runners, $95

Ok, I lied. I have two pairs of these wool runners, and I forgot about them because they’re a bit light for winter. I have one pair in bright orange and one in light gray. They’re really lightweight — you feel like you’re walking on air — but don’t have a ton of support, so don’t go for miles in these. They have odor control and moisture wicking elements, so you can also wear them without socks. They’re great for a quick tool around town, AND THEY ARE WASHABLE. Their loungers are awfully cute, too.

2. Gentle Souls, $99.95

My husband has a pair of these and loves them. I’m fond of these zippers.

3. FitFlop Sporty-Pop, $150

Oh, this lovely pink color — these are mighty fetching and get high marks for comfort. I wore out my Fitflop sandals a few summers ago and since then have been eyeing the brand for new designs. Now they have our 46-year-old sister Uma Thurman repping them, which feels so spot on demo. Also, these in purple? Whoa.

4. Ugg, $109.95

I dig the bright red of these jaunty slides. Good job, Ugg.

5. Vionic, $129.95

Vionic makes shoes that even Dr. Andrew Weil will vouch for. This variation on the omnipresent perforated sneaker-slide has a nice twist with the little diamond chips. The grey shade is so chic.

Sandals

6. Gabor, $189

This is just a fabulous black shoe with a thick-ish white sole and a perfect silhouette. Rave reviews online.

7. Worishofers, $75

These are either wildly ugly or edgy in their granny style. Maybe less edgy when you actually are a granny, but I think they’re cool in gold.

Clogs and Slides

8. Birkenstocks, $135

Yes, we know your “Arizona” White Birko-Flor sandals are a staple, what about these psychedelic tourmaline-colored versions? Or maybe these blue suede shoes with a denim colored vibe?

9. See by Chloe, $255

These have a nice, thick modern sole with a classy profile and gold buckle. Just dig ‘em.

10. Free People, $98

Backless mules are all the rage, and these are super cute with a padded footbed. I like the black suede, but they also come in party-ready grape metallic.

11. BRYR, $258

I adore clogs — but some are better than others in terms of comfort. I haven’t tried these, but I love their curry yellow color and the low heel. Will somebody try them and report back?

12. Pikolinos, $149.95

I love my Pikolinos. The cork sole and the blue leather are understated cool.

Flats

13. Melissa, $105

I’ve long been a fan of Melissa shoes and their plastic comfort. This collaboration with Jason Wu is lovely, simple and everyday.

14. Born, $90

Born makes great shoes. These just seem totally useful with a summer dress.

Boots + Oxfords

15. Steven, $99

I’m not sure why I like these, but I do. These Pippar Cutout Oxfords have a decidedly glitzy ‘80s vibe with a rose gold color that’s so hot. There would be amazing with jeans.

16. Officine Creative, $535

This is a Kim France pick, from her excellent fashion-centric newsletter Girls of a Certain Age. Quite spendy, but so sharp — plus, this almost-cowboy-shape is always comfortable.

17. Earth, $119.95

These aren’t quite my style, but I might try them — they get huge raves online.

 18. Fly London, $179.95

Another version in the peep-toe bootie. This navy is perfect.

What are your favorite, most comfortable shoes? I’m still on the hunt for a perfect loafer. Any suggestions?

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(Image: Isabella Giancarlo/ TueNight)

Originally Published April 11, 2017. Updated April 15, 2021.