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Photo-Illustration: The Strategist; Photos: Dominique Pariso, Tembe Denton-Hurst, Najwa Jamal
Now that temperatures have dipped in New York, open-toe season has come to a close. Sandals have swapped in for boots, loafers, and other cold-weather fare. Curious about what shoes New Yorkers are wearing this season, three Strategist writers canvassed the city, stopping people on street corners in the Flatiron District, Fort Greene, and the Upper East Side. We approached people on their way to the office, while they drank their afternoon coffees, as they were walking their dogs, and right before they hopped into an Uber with their groceries. We asked about comfortability and wearability, nodding knowingly when they gushed about the magic of zippers, blister-free leather, and the enduring appeal of Frye boots.
Ballet flats abounded in various heel heights, loafers showed up in different shapes and colors, and leathers, suedes, and croc-esque textures were on display. And as was the case when we asked New Yorkers about their work bags, plenty of secondhand and vintage finds sourced from eBay and Poshmark were in the mix, too. Below are all the shoes we spotted, shared with the permission — and thoughts — of their wearers.
“I’ve worn these Jeffrey Campbell shoes for the past three months. They’re pretty much broken in; I wear them 24/7. I have a little bit of a bunion and they don’t bother me at all, or on the back of my ankle. They’re suede and leather and kind of like Tabis, which many of my friends have and need to resole. You can see the bottoms here — I’ve worn them a lot, and especially against New York City concrete sidewalks, the soles still look really good.”
“I got these in the Netherlands at the Posa store. I think they’re very cute — you can combine them with everything; that’s why I love them. And they’re very comfortable. I’ve had them for two months. I wear them to study, and yesterday, I walked 30,000 steps in them without any blisters or anything.”
“I love these because they are suede and very comfortable. I bought them about a year ago, actually. Straight out of the box, I wore them without any blisters. I walk a lot and wear these a lot, two to three miles at a time, and they still look pretty great.”
“The shoes are by a former ’70s Japanese brand called Haruta. I acquired them at Front General Store in Brooklyn. They’re super comfortable. I’ve owned them for about two years, but the wear on them does not reflect that.”
“I bought these in Park City, Utah. They’ve been interesting. It took me a little while to get used to them, but I like them now that I’ve broken them in. They feel sleek and cool.”
“I bought these on the RealReal. They took some breaking in and I had to add a thing in the back to make them more comfortable, but now I wear them all the time.”
“I wear them everywhere. Whenever I travel, I bring them because you can pair them with a casual fit but you can also dress them up.”
“I saw these in an ad and Google reverse-image searched. We were comparing them to Tabis last night. They’re Tabi-shaped but without the indentations.”
“I usually buy expensive shoes, but I took a chance on these. They’re from Zara, so I don’t know how long they’ll last. I got them in Paris.”
“I’ve had these for three months. They’re super comfortable. No break-in period. Daily 10,000 steps are no problem, and the most I’ve done in them is 25,000. I haven’t put on my Salomon sneakers in a very long time because of that. The cut in the front reminded me of the Loro Piana flat, which I wanted for so long. The rubber on these makes them really great for walking because I feel like they’re absorbing some of it. I love the little V in the front and the square toe. I think it’s, like, a really elegant shape.”
“I’ve had these for two seasons now. I also got them in tan suede. They come in a lot of different colors, and they’re really very comfortable for walking in the city. No blisters or breaking in — absolutely nothing. I think I may be getting them in burgundy. They’re so comfortable. Just put them on and go.”
“These are suede loafers from G.H.Bass, and I actually bought them recently. I was looking for something that looked nicer than a beat-up sneaker. They’re comfortable and I can slip them on easily when I’m walking my dog, Banchan.”
“I’m obsessed with them. It’s this French brand called Soeur. I wore them all summer long. I wear them almost every day. You can hike, you can run, you can dance, you can do anything — no issues. I want them to last forever.”
“I got them from the Korner. I’m from Hong Kong, and they’re a very popular Hong Kong brand. I love how versatile and comfortable they are. I wear them to conferences, work events, and also just on a nice Sunday afternoon. I’m usually in scrubs and Crocs, so it’s nice to wear something more cute.”
“I actually just got these yesterday from Asos. I work in a corporate office, so I’m trying to be professional but make it a little bit more fun.”
“They took a while to break it. I have another pair of Tony Bianco boots that were way more comfortable. These took maybe 15 times wearing them. I also went to town with a hair dryer. But now they are like slippers. Anytime where I used to wear a sneaker, now I wear these.”
“I was on the hunt for a long time for the perfect loafer. I saw these at a store in Easthampton and I was like, Okay, wait, these actually look exactly like the shoes that I want, because I wanted them to be comfortable and something that I can wear all the time. I’ve had them for a few months now, and they’ve stretched to my foot nicely because I’m walking everywhere. It’s been a perfect, comfortable everyday shoe. People think they’re The Row.”
“I’ve had these for years. They’re cute little pony-hair slingback flats from Schutz. They’re just so easy to slip on when I walk my dog. They look like slippers, right? But they have an elastic slingback. You’re the third person to compliment me on them. The thing is it’s a little bit of a conundrum sometimes because it has to be the exact right temperature. They’re sherpa-lined, so it can’t be too hot, but if it’s a little bit too chilly, like it was this morning, then I need to put socks on.”
“I was at a Buffalo Exchange in the Bay Area and saw these brown oiled Danskos and knew I had to add them to my Dansko collection. I have three pairs total: classic black, these brown, and a calf-leather kind of furry pair that people really love. I love the arch support. I love that you can kick them on and kick them off super easily. They’re heavy in the rotation. I will say the thing with Danskos is, for people who are not used to them, you have to figure out how to walk in them a little bit because of the platform. You have to be careful, or you will stumble. The city can be a little precarious for a Dansko wearer.”
“These are from a Japanese company called Hender Scheme, and they’re leather craftspeople. They normally make very simple, basic leather shoes, and then these were just a crazy mash-up that I thought were so exciting and had never seen before. This was my first purchase from the brand. I had been waiting for the diamond in the rough. They are incredible. Their craft and their quality as a maker in the shoe space really stands out.”
“These are Arc’teryx slide-on shoes. If you’re ever going climbing outside, they’re grippy for the mountain leading up to your climb. They’re also really comfortable and go with everything.”
“I’m wearing these amazing knee-high — I’d say white — boots from Frances Valentine. They’re literally so comfortable. They have a little block kitten heel. I have been wearing them for a few hours and could walk all around all day. I feel like the designer really knows what she’s doing. I mean, she knows that women in New York walk. I just got them for fall, like, a week ago. This is also the first time I’m wearing them, so this is the break-in walk, and I’m totally fine. I got them in red too. I’m very happy. They’re a good heel height too — not too high, not too short. Once it gets colder, I feel like it’ll look cute under pants also, so they’re really versatile.”
“These are my Steve Madden cowboy boots — but they have a zipper on the side, so they’re very easy to put on, not like a classic cowboy boot. I’ve had this shoe for, like, four years, and this is my second pair because they just wear in the heel a little bit. I loved them so much that I bought them again. They’re extremely comfortable. I walk very fast — like, I’m booking it getting on the subway — and I’m tall; I’m 5’9. So I feel like I’m naturally faster than people and step harder than people. So these wear well. I have to get another pair soon.”
“These are my party shoes. I’ve had them for over a year now, and they’re cute. I like that the fabric goes over the boot.”
“These are comfortable and easy to walk in. I also like that they zip on the side, so you don’t have to worry about the shoe strings.”
I just got these, they’re Sam Edelman. They’re brown leather and very cute.
“These are dupe Frye boots — like, 60 bucks on Amazon. We’ve been beep-bopping all day, no pain. Super comfy, would recommend!”
“I spent way too much money on these, but unfortunately, I love them. I wanted to hate them so I could return them and not feel guilty. I’m thankful for Afterpay.”
“I found these on Farfetch. I bought them on sale and still paid too much for them, but I love them so much. An Everywoman’s witchy October boot.”
“I bought them at Shoe Market on Bedford at the start of winter. I love the little square toe box, which is kind of fun, and I like that they’re actually quite comfortable. And they’re actually warm. I’m very much a form follows function kind of gal.”
“These were a Christmas gift I got about three years ago now. A great gift. One of my favorite pairs of shoes. They have a very nice wooden heel and definitely make a bit of a statement whenever I go out. The quality is kind of unmatched. They hold up. I’ve never had to take them to get fixed up at all. I take care of them; they take care of me.”
“One of my best friends works for the brand. She initially bought them in red, and I loved them so much, so she purchased them for me in black. I love how shiny they are, and I love the heel — it’s super chic but really easy to walk in. And I love how the toe is rounded. I’ve had them for about three or four years. They’re incredibly comfortable. I’ve probably walked 5,000 or 6,000 steps in these at a time. They just released an updated version with more of a pointy heel, and I did just purchase those as well.”
“I was looking for the perfect boot for two years. Knee-high, kitten heel, pointed toe. Took me so long to find them. I used to have a Naturalizer square-toe boot, and they stopped making that style. So I had to replace it, and I just decided to split up my needs: one pair that’s a cunty, pointy boot and one more heavy boot for everyday. So this is the pointy pair. They’re so comfortable. Naturalizer is a brand that’s known among older ladies for being super good on the feet. I wear them to work. I wear them to dinner. Any kind of event where I want to feel a little more fancy. But they are so comfortable that I could wear them dancing. Everyone should know about Naturalizer.”
“I actually got them on sale at Nordstrom, and they’re Nine West. They’re extremely comfortable. They’ve held up well while I commute. I easily walk two miles in them every day. They fit true to size on me, but I do have very narrow feet.”
“They’re black patent-leather Chelsea boots from J.Crew. They’re easy to slip on and walk around in. I was just on my way to the farmers’ market this morning, and it’s even easier than slipping on a pair of tennis shoes. The heel is starting to wear away a little bit, but this is after two solid seasons of use wearing them three to five days a week.”
“These are secondhand Danskos from Poshmark. I got them last week, and I’ve worn them almost every day. I love that they’re monochrome. I feel like it’s hard to find a heel that is also black when you’re looking for black boots. They’re supportive. And they just slip on. I only buy vegan leather usually, but now that I’m buying secondhand, I’m expanding into genuine leather, so now I’m going to get all the Danskos.”
“I got these two years ago. I saw some girl on TikTok had them, and I thought, I need those shoes, even though they’re more expensive than any shoes I’ve ever bought. They go with everything. They’re super cute. I’m short, so I always wear heels, but they kind of look like flats without being too much of a heel. They’re so comfortable. I walk 10,000 to 15,000 steps around the city. I was going to get them in another color, but I wear a half-size, and they stopped carrying 6.5.”
“A bit mainstream, but I thought they were a bit cute with the little heel. I’ve had them for two months, and they’re very comfortable.”
“I love these. Maison Margiela. They’re raffia, so I thought they’d be for the beach.”
“I picked them because I really like the color. I feel like it pops. And they’re comfortable.”
“These are Golden Goose and I got them on the RealReal. I’ve had them for over a year now, and they’re very comfortable. I wear them a lot.”
“I have owned these for nine years and worn them across the country. I love them so much; they’re my best friends.”
“These are some worn-in brown boots from Frye that I stole from my boyfriend. I’ve had them for seven years. They’re leather that’s super worn in and soft. At this point, it’s like a second skin. I think that they’re pretty true to size. I do have a pretty bony foot, so thick socks are always a must for me — but with a thick sock, they do the job.”
“I thrifted these. Once it’s fall, I’m always excited to break my boots out. I was kind of rushing over here for work. So I said, What’s going to get me to and from while also maintaining some level of style? These are just always easy to wear. It’s nice to know that I can always come back to these. They’re classic.”
“I got these boots on eBay. I was looking for a new pair because the toe kept splitting on my favorite pair and I kept getting them repaired. So I just figured that I need to get real quality boots. The listing said they were handmade in Mexico. They are magic. I’ve walked 20 miles in Manhattan in them. They literally go with everything. I’m wearing them with a dress right now, but they look really cute with shorts. They also look really good under a pair of jeans, as well, with just the little toe poking out. My feet are a size 11, so every time I’m looking for shoes, especially on websites like eBay, I always just put my size in the search term because I’ll take whatever I can get. My guess is that they’re men’s boots because they are really wide.”
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