My Hunt for an Actually Comfortable Pair of Starter Heels

With a darling bow and ever-so-slanted square toe, these slingbacks are pretty much exactly what I want to see peeking out of my wide-legged jeans. Unfortunately, the shoes are notably stiff out of the box, and, accordingly, gave me more blisters than I could keep track of. My first mistake, perhaps, was doing my inaugural test during a lengthy walk from the train toandthrough Brooklyn’s Navy Yard. I only made it about half a mile before the skin on my pinky and index toes was rubbed raw enough to justify calling an Uber. By the end of the night, my boyfriend even offered to carry me home. (I politely declined.) I had to walk, nay, hobble myself home for the sake of journalism. Needless to say, backupflatswould join me going forward as I continued to test these. Each time I wore these heels after that fateful evening, I didn’t make it very far. I don’t have the patience or pain tolerance to break them in.

After reading that our contributor Katie Stone’s biggest gripe with Quince’slug-sole loaferswas that they weretoocomfortable, I had high hopes for its heels. Like the loafers, the slingbacks have an OrthoLite insole, which I found supportive. But unlike some of the other pairs I tried, these heels have an elastic ankle strap (rather than an adjustable one), which dug into my ankles an hour or so after I slipped the shoes on. Sometimes, I would even have to slip off the strap to bring some relief to my ankles an hour or two into the night. The shoes were ultimately too tight at the toes and ankle strap for my liking.

I’ve often coveted a double-strap (see: theFlabelus mary janesI can’t stop thinking about), so visions of the outfits I’d create with these dainty white heels floated in my head long before they arrived (many of the sizes are available on a preorder basis). Unfortunately, when the heels finally arrived, I found that the third strap on these — the heel strap — was, well, the shoes’ Achilles heel. Though the shoe has both elastic and an adjustable buckle, the strap would slowly slip down my heel no matter how loose or tight I made it. Thefaux-leather encasing on the elastic also ripped after just two wears, making the shoes look cheaper than what they are: the most expensive pair on this list. To me, these shoes are cute enough that I’d still wear them on a dinner date, but the constant readjustments I found myself making while wearing them make them unreasonable for an entire day of walking.

After wearing heels of varying heights and widths all summer, I feel confident saying these are the sturdiest of thetallheels I tested. Their chunky heel brought stability while speeding down subway stairs and strutting through the Port Authority tunnel. But, again, these shoes lost me at the heel strap, which is slightly too tight — albeit elastic — and lacks an adjustable buckle. Though they’re not as tight as the Quince heels above, the straps dig into my heel too much to make the shoes comfortable enough to wear for an entire day.

If you’re looking for a pair of heels that you can comfortably wear for a few hours while running down subway stairs, walking across cobblestoned streets, and wandering around the neighborhood, these are for you. They have a wide, sturdy heel that’s short and sturdy enough that I don’t even feel like I’m wearing heels when they’re on my feet. It’s only at the six-hour mark — when the rubbing on my big-toe knuckle became noticeably uncomfortable — that I would stop recommending them. This, paired with slight rubbing on the side of my foot from the inside part of the strap, made these heels fall short of the crown.

I won’t lie: This article was the only thing motivating me to wear heels multiple days a week. Still, I know I’ll be wearing these heels with jeans and dresses long after this story goes live. Similar to Rothy’s, Vivaia’s shoes have ultracushioned footbeds that make walking in these heels all day actually possible (and comfortable, no less). Barring an initial run when I noticed some rubbing on my toes and had a few close calls with twisted ankles, these shoes quickly became one of my favorites. Despite having a skinny heel, they’re sturdy enough for modest jogs down subway stairs and comfortable enough to walk multiple miles in. Plus, the adjustable strap makes it easy to adjust to the perfect fit.

Considering that Madewell makesmy favorite mary janes, I’m not surprised that it would make one of my favorite pairs of heels, too. They’re the only pair on this list with zero break-in time and are made more comfortable by an adjustable heel strap that I found came in handy when my feet and ankles swelled on steamy summer days. By now, I’ve perfected the strap to the point I can just slip them on — and isn’t that half the appeal of a non-heel? If I have to give the pair one critique, though, it’s that especially during the beginning of my hunt, the skinny, tall heel caused my ankles and lower calves to strain. As I perfected my Carrie Bradshaw run and built up my ankle strength, this went away, but I think it’s important to note if you, like me, are giving heels another chance after a lengthy hiatus. Needless to say, these, along with the Vivaias, will live on the top shelf of myshoe rackfor the foreseeable future.