I Walked 5+ Miles All Over NYC in These Heeled Sandals—5 Pain-Free Winners

My closet isn’t just full, it’s absolutely overflowing. In addition to everything hanging on racks, I have an entire shelving unit dedicated to my shoes and that’s not even counting the 15 or so excess shoe boxes that are currently being used as a bedside table. Yet out of all that, only about a handful of the shoes in my collection are actually comfortable, which doesn’t bode well for someone who lives in New York City, where walking is the primary form of transportation. With summer in full swing, I’m walking more than ever, so I decided that it’s finally time to invest in some footwear that won’t leave my feet beat up and blistered for yet another summer. Sand might be a natural pedicure, but even the whitest of beaches can’t fix my toes after a summer of days spent stomping on concrete in four-inch heeled flip-flops. In order to find out which shoes—specifically heeled sandals—successfully combine style with comfort, I took a few buzzy pairs out for a true NYC test: 10,000 steps (or roughly 5 miles). See which heeled sandals I’d dare to wear again after running around the city in them. The massive Nordstrom sale is filled with plenty of gems, but despite all the epic deals to be had, I still think these $50 sandals are one of the best finds. Not only have they been one of our top-selling products this month, but Nordstrom shoppers seem to be as obsessed as our editors are—the last time I looked at the product page, the retailer told me that 50 people were also viewing them. So of course, I had to see if they were really as good as everyone seems to think they are, and my test for a good pair of shoes is whether or not I can wear them all day (and night) in NYC without having to hail a cab to get everywhere that I need to go. First things first, the strap on top is padded, so it genuinely feels like a pillow for your feet. Not only that, but it features a velcro strap so it’s adjustable to your feet (rejoice, my wide-foot friends!) and a wide heel that provides plenty of support. After weeks of testing different heeled sandals, I was used to skinny straps that mark up my toes or skinny heels that I can’t help but wobble in. These absolutely did not do either. In fact, I decided to wear them out to dinner and walked from my apartment in Gramercy Park to Tribeca in them. That’s approximately 2.5 miles. If that’s not proof enough that they’re worth investing $50 in, what is?  Okay, Reformation, you really popped off with this one. I’d been clocking the brand’s cool shoes ever since they launched into the category, but had never had the chance to try them out myself until now. It may have taken me this long to get on board, but now that I’ve experienced them IRL, I’m never going back. I tried two pairs of their heeled sandals and while they both won me over aesthetically, it was the Enya Wedge that was took the cake for comfort. Wedges offer the most stability of any heels and these were hardly any exception. Usually a thick strap can make my feet feel vacuum-sealed in, but this pair is made from the most buttery-soft leather, so that was simply not at all the case. I could have walked miles (and did) in the three-inch heels, but not only did they deliver in the comfort department, the cutout heel shape also hit on a major 2023 shoe trend. So it’s really a win-win.If you’re looking for wearable heels that strike just the right balance of cool, heeled flip-flops are it. Endorsed by best-dressed A-listers like Kendall Jenner and Zoë Kravitz, this shoe style adds just the right amount of casual cool to your outfit. But because they have minimal straps, they can quickly get uncomfortable, which is why I beelined to Tamara Mellon, a brand known for making sneakily comfortable heels. Like many of Tamara Mellon’s heels, the Luster 40 sandals feature a memory foam-like support layer I can only describe as cloud-like. Normally, heeled thongs start to become annoying after an hour or so, but I could have run a marathon in these, despite their minimal straps.I lost count of how many years it’s been since I first decided I wanted a pair of Maryam Nassir Zadeh’s cult-favorite Olympia wedges. I think I’ve been eyeing them for the better half of a decade, and no, I’m not exaggerating. The only issue is that they sell out faster than Aimé Leon Dore New Balances and were always fairly out of my price range. This year, though, I finally decided to splurge on a pair when they were temporarily discounted during the Ssense sale and was downright shocked at how comfortable they are. I always figured that PVC shoes were miserable to walk in—something about the edges of the plastic just seemed akin to footwear torture—but I couldn’t have been more wrong. I’ve walked far more than 5 miles in these and can say with 100% certainty that I’ve never owned more comfortable heeled sandals. I’m convinced it’s the wedge heel, which is why I’m investing in many more wedge styles this season. I’d heard from my coworkers about Paige’s shoes and how, thanks to their signature cushioned insoles, they are surprisingly comfortable for long-term wear. And just like most of the sartorial advice given to me by my fellow editors, they weren’t wrong. These mules have a nearly four-inch heel, making them far taller than the sandals I most often frequent. Yet they were a breeze to walk in and climb stairs in, which I had to do a lot of at all the Midtown F stations I visited during a long day of press previews. The thicker the straps, the better when it comes to comfort. I could go for miles in kitten heels.If you’re ready to splurge on some wedges this season, these are the ones to invest in, and not just for their looks. They feature a gripped sole for added stability as well as a soft leather strap that’s made to stretch and mold to your foot. Pretty!Wallet and feet-friendly.Yes, these are as wildly comfortable as they look. I’m not exaggerating when I say they’re like walking on clouds.Don’t let the tiny straps fool you, Larroude’s shoes are made with the highest quality materials, so you know they’re going to be easy on your feet.The puffier the straps, the better.With so much surface area on the foot, you’ll never get a blister wearing these.The wider the heel, the easier they are to walk in.I love when an item is as easy to style as it is to wear.Mango’s kitten heels are some of my all-time favorites.When in doubt, go for a tiny heel.