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Can heels really be comfortable? As a 5-foot-3 woman, I’ve certainly tricked myself into thinking so, especially on those rare days I spend mostly sitting at my desk. (It’s easy to talk yourself into a less-than-ideal pair when you aren’t walking further than the conference room.) I like a little extra height, so I tend to wear heels almost every day, even during New York Fashion Week, when many of my colleagues have switched to flats or sneakers. The options are simply too tempting; my collection of (mostly uncomfortable) heels has grown substantially, and lately I’ve been scouring The Real Real and vintage shops for wobbly stilettos from the ’90s, or another pair of knee-high boots I really don’t need. There are just so many shoes that are too good not to buy—and usually it's the most impractical styles that are most irresistible.
When it came to finding the right shoes for Fashion Week, I had to take a long, hard look at my closet. I do have plenty of flat shoes too, but for the purpose of this story, I wanted to find the ultimate comfortable heel—so I put a few pairs to the test. I’d wear them during one of the busiest weeks of the year, ideally without risking any blisters or serious discomfort. Lots of women seem to be on the same page as me; the days of “needing” to wear heels are behind us, but designers like Daniel Lee at Bottega Veneta are inspiring an embrace of heels again (particularly his sold-out, square-soled mules, if you can snag them in your size). Over the course of four days, I wore four different pairs of heels for back-to-back shows, appointments, and presentations, tracking my steps on my Health app, discovering that I averaged seven miles per day. Despite the early start times, late nights, and dozens of subway rides, the best heels I found didn’t slow me down at all.
Sure, my legs and feet were tired, but that’s inevitable at NYFW no matter what you’re wearing. My first shoe was a pair of 3-inch wedges by Staud. Their moderate height and slim, gradual wedge kept my arches happy, and the single strap allowed my feet to breathe. They were easy to slip on and off for some midday ankle rolls, and my toes never felt cramped. They passed the test without a hitch.
The second shoe was an oversized block-heel boot from Dries Van Noten. I bought them on The Real Real on a whim one day when my colleague convinced me that I “needed them”—and she wasn’t wrong. The large surface area of the thick heel made these boots a fashion week no-brainer. But despite feeling grounded all day—never wobbly or in pain!—there was one con: It was a lot hotter than I expected, and my socks, well, they got a bit sweatier than I’d hoped. Still, I was able to keep up on a 20-minute walk to a cocktail party with a fellow editor—and she was wearing Tevas.
On my third day, my feet were tired from the non-stop schedule, but I had to put a micro-kitten heel to the test. I was a little nervous about my 5.2 cm Virgo sandals from By Far, despite the fact that they’re so much lower than my other heels. I’d only worn them a couple times, and their dainty straps made me doubt they could hold up on a 10-plus hour day. Much to my surprise, the only thing I had to worry about was the small spike getting stuck between cobblestones and cracks in the street. They were so lightweight I felt like I was wearing flats.
Last but not least, the highest pair of shoes I wore all week were 3.5-inch wide-heeled, square-toe pumps by Wandler. Surprisingly enough, they were also the most comfortable shoes I wore. They were roomy enough to give my feet room to breathe, and I could even wear socks for a little added comfort. The silhouette supported my ankle from a 9:00 a.m. presentation all the way until Rihanna’s Savage x Fenty show in Brooklyn at 9:00 p.m.—and, it should be noted, they garnered the most compliments, too. Their half-brown, half-cream design lent a dose of chicness to my all-denim look and nailed one of my favorite trends of the moment: two-tone shoes.
Four heels and 55,530 steps later (that’s 24.2 miles—almost a full marathon!), I’m happy to report that I survived without so much as a blister. Even with the alternative and popular styles like sneakers, loafers, and Havaiana flip flops that have taken the streets by storm, sometimes a foam or cork footbed aren’t always the key to happy feet. If you’re in the mood for something a little more elegant, consider these comfortable heels as the ultimate compromise. After a surprisingly easy day in patent pumps, eight shows in a pair of block heel boots (shop similar styles here for fall), and two pairs of heeled sandals, here’s to putting your best foot forward, in what are now confirmed as the most comfortable heels for fall.
