When it comes to comfortable shoes, Naturalizer has long had a reputation for keeping feet happy. However, say the words “comfortable heels” for any brand and I’m immediately weary. I finally decided to see if the hullabaloo about the brand was true, and set out to see how far I could walk in Naturalizer heels. Below, I tested two different styles to see how long I could stay on my feet.

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How I Tested the Shoes

I wore each pair of shoes fresh out of the box for a full day’s worth of activities in New York City. When evaluating them, I weighed factors like design, heel placement, width, material and overall comfort to determine if I’d wear them again, and made notes of when, where and if my feet started to hurt. For reference, I wear a size 6 and have flat feet and bunions.

Elaine Slingback

I wore the Elaine slingbacks out on a Saturday to attend several events. First was a croquet party. I took the bus, so by the time I walked to the bus stop and walked into the park, I had covered about 0.75 miles. After several rounds of croquet, I left to host my classics book club in Midtown. At that point, my heels and arches felt fine, but the tops of my toes were starting to rub on the shoe.

I walked to the subway and, thankfully, the meeting spot was in front of a subway station, too. 0.4 miles. After book club, I went across the street to meet a friend for drinks, and then afterward, walked them down to Union Square before going home. 1.5 miles.

Total Miles: 2.65

Jayla Slingback

I wore the Jayla slingbacks to the office. The morning commute is 1.2 miles, since I live a bit far from the subway, and the office doesn’t have many subway stops nearby. When I got off the train, I noticed that the slingback continually slipped off my heel. After grabbing snacks and settling into my desk, I work until lunch when I like to take a walk. 1 mile. Then, I do the commute home, another 1.2 miles.

Total Miles: 3.4

Elaine Slingback

• Design: I was wary at first—the cut of the shoes reminded me of Marc Jacobs’ spring 2025 collection…a bit “Toon Town” -esque. However, they grew on me, and I do like the aforementioned aesthetic.
• Heel Placement: This surprised me a lot. The heel isn’t inset but the shaft is angled. Wow, that made such a difference. It put the majority of the weight on the ball of my foot and the middle of my heel, as opposed to letting everything sink on the back. I walked a lot farther than I was expecting to in skinny heels. The angle also makes the shoes comfortable in that they didn’t feel like 2.5-inch heels. They felt like 2-inch heels.
• Width: There are two widths, medium and wide. I wore the medium, but I think my main comfort issue—pinched toes—would have been solved with the wider width.
• Material: Soft, smooth, no break-in time needed. That was another pleasant surprise. The slingback also stays in place without rubbing or chaffing.
• Overall Comfort: I’m incredibly impressed I walked over 2.5 miles in these shoes, given the design. At the end of the day, having traversed concrete, grass and gravel, my arches and heels felt great. I do have hammer toes (the fourth toe on each foot), which after a day’s walking started to rub uncomfortably on the roof of the shoe. Again, I think that if I had worn the wide width, the extra material may have helped with breathing room.

Jayla Slingback

• Design: I beelined for these because of the 1-inch block heel and square toe box. They’re not the most exciting design, but I got compliments on them—especially for the color.
• Heel Placement: A block, 1-inch heel can’t do much wrong. It was a comfortable height with a little boost.
• Width: Medium and wide. I went with the wide and found that I didn’t have any blisters after nearly 3.5 miles. However, even with the wide size, I did feel a bit constrained, mainly in the bunion area.
• Material: This depends on the color, but mine were faux leather and felt a little more plastic-y in that the material wasn’t as soft. However, it was still very flexible and I didn’t find a break-in period necessary.
• Overall Comfort: These ones were a hit-and-miss. I love the low heel and wider toe box, but the angle of the slingback meant it was constantly slipping off my heels, and I ended up with cramps on the tops of my feet and angles from trying to keep the shoes on.

The Bottom Line

Naturalizer does live up to its reputation for creating comfortable shoes. In all the miles I walked, my arches did not hurt, nor did my bunions. Everyone’s feet are different, but I would personally prioritize a wider width to accommodate my toes on long walks. With both pairs being under $160, I think the brand hits a reasonable intersection of design and quality. In this instance, my recommendation is the Elaine slingback for its supple leather and unexpectedly comfortable heel design for nights out. The Jayla’s design is more suited to casual looks. So now if you’ll excuse me, I’m off for another round of croquet.

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