Finding the right footwear for city living is a delicate, wretched dance between choosing style and comfort. New York City sidewalks are a minefield, littered with hot trash, slush, and feisty rats, and feet need sturdy armor in case they get trampled in the crush of a subway car. This is why when Jezebel Deputy Editor Alexis Sobel Fitts asked me to find her an everyday sort-of flat shoe she could take from, as a copy of InStyle magazine circa 2002 would say, “day to night,” I cracked my knuckles and accepted the challenge.
Fitts’ criteria for “an everyday flat/shoe to wear 99 percent of my waking hours” was a pair that she can wear to a nice situation but were comfy enough that she could “tromp around” the city in them, and arch support was a plus. She also had technically found the ideal cute low-heeled shoe in an expensive pair of red Gorman Pebble Pumps, which sold out before she could snatch them up. With Gorman’s cool minimalism in mind, I set out to find comfy flat or low-heeled shoes that were fit for a fancy dinner and a walk through Prospect Park.
Everlane Day Heel ($58)
Everlane’s office casual offerings tend to skew a little too plain in my opinion and I’m a firm believer that nobody should wear clothing designed for the office outside of an office (be free!) But the brand’s red Day Heel is the closest, most affordable dupe for Alexis’s ideal Gorman pump, even down to the coral-adjacent red color. Currently on sale in a few sizes for $58, the rounded toe and low-heel combo basically guarantee your feet won’t be blistered from a day walking around.
Soft Styles Women’s Angel II ($49.95)
I’m sort of obsessed with these Angel II pumps from Soft Styles, an offshoot of the classic Hush Puppies brand, which promises “extra cushioning for maximum comfort.” The shoes are basic to the point that they sort of like the platonic ideal of a heeled shoe, and they come in a variety of colors including red, white, and baby (or “millennial,” eye roll) pink. This might be my personal affinity for “so ugly it’s good” style or my die-hard love for Working Girl talking, but these pumps are giving me ’80s executive in a good way?! Remember, girlboss style is only cool when it’s camp!
Vionic Natalie Pump (139.99)
Vionic is a brand that makes shoes with extreme comfort in mind, emphasizing arch support and “heel health,” and the brand was actually started by a podiatrist. And if all of that screams “oh god these shoes are going to be ugly as hell,” Vionic’s are surprisingly not your grandma’s clunky supportive shoes. They make a wide variety of shoes with no bells and whistles, and their Alexa Flats and Jade Slingback Flats are cute and simple, with a little extra oomph to keep your feet from feeling like hell after a long day. I am extremely into these Natalie pumps, which don’t even look close to being borderline-orthopedic.
Madewell The Cory Flat ($110)
While the Cory might not offer much in the way of arch support (though Madewell promises some cushioned padding) the boxy, soft leather shape makes the shoe a little bit cooler than your basic ballet flat. It’s simple enough to go with literally everything and nobody would blink twice if you wore them with a nice dress to a casual wedding.
Vagabond Joyce Pumps ($120)
Please don’t scream at me for recommending a suede shoe, but these Vagabond Joyce heels are sort of my ideal “I want to spend most of my waking hours in these” shoe. While they only come in two colors (black and cream) they have just the right amount of heel to elevate them out of flat territory without making the shoe look like it’s meant for a child.
Readers, do you have any suggestions for Alexis?