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

Summer is in full swing, and as someone who lives in New York City, where walking is the primary mode of transportation, I'm definitely getting my steps in. It's not unusual for me to hit the 10,000-step threshold in a given day, but in peak summer right now, that's looking a lot more like 15k+ between press previews, meetings, happy hours, dinners, and everything in between that's filling up my calendar. On busy days like these, it's tempting to slip into my favorite sneakers and call it a day, but instead of reverting to them out of habit, I challenged myself to source heeled sandals that are chic and actually comfortable, and the results are in.

I don't know about you, but I've hardly experienced a single summer that didn't leave my feet beat up and blistered from a pair of ill-fitting shoes. 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 five miles). 

See which heeled sandals I'd dare to wear again after running around the city in them. 

Nordstrom's shoe section is filled with plenty of gems, but despite all the solid options, I still think these $75 sandals are one of the best finds. Not only have they been one of our top-selling products this month, butReplica Store shoppers also seem to love them as much as our editors do. 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. 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. The shoes feature an adjustable Velcro strap (rejoice, my wide-foot friends!) and have 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 $75 in, what is?

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Okay, Reformation, you really popped off with this one. I'd been clocking the brand's cool shoes ever since it 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 the brand's heeled sandals, and while they both won me over aesthetically, it was the Enya Wedges that 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, but the cutout heel shape also hit on a major 2023 shoe trend. So it's really a win-win.

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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 cloudlike. 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.

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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 Wales Bonner Adidas 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 five 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. 

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I'd heard from my co-workers 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 fashion 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 subway stations I visited during a long day of press previews. 

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More comfy sandals that were made for walking: