One day many years ago, I limped home with another stinging blister and texted my friend Sydney: “Is there a single woman’s shoe that was actually designed to touch human skin?”

Are human feet evolutionarily designed to wear shoes? Is it your foot breaking in the shoe or the shoe breaking in your foot? Is there a world in which I don’t pack emergency socks in my work bag? What better time to get to the bottom of it all than the middle of a sweltering hot New York summer?

As a devout pedestrian, one of the most vexing parts of summer’s arrival is figuring out what goes on the feet. Cold weather is easy. My soul clomps around in boots; if I ever strike it rich, I will have one closet dedicated to hundreds of them. Sandals in the city do not speak to me. I’m left with flats, the only silhouette that looks natural with summer ensembles. So I evaluated about ten pairs and found five that earned their place in the weekly rotation and on my shoe rack.

My assessment involved walking at least 10,000 steps in a day with each of these pairs (one cannot trust the shopping recommendations of people who Uber everywhere). There were hot days when I waited in the shade for the crosswalk light to turn, taking a good long look at myself in the window reflection of the Manhattan Footcare on Brooklyn’s Smith Street. I, of course, am not advocating for hitting the pavement in shoes that provide little support. The older I get, the more I understand how incremental behaviors add up and reverberate throughout the body. And yet sometimes, aesthetic preferences and logistical circumstances of a life on the go necessitate skipping around town in a dainty little shoe. (To offset the days I spent testing these flats, I logged a lot of recovery time in my favorite supportive shoes: the Asics Superblast 2, the Karhu Mestari street sneaker, and the Norda 003, a trail shoe made for people like me who haven’t the patience for tying shoelaces.)