Heel lovers have had a hard decade. About ten years ago, sneakers began popping up on the runway (see: Chanel Spring Couture 2014 and Balenciaga Fall 2017); first slowly, here and there, then suddenly… everywhere. Not only did it become socially acceptable to wear flats, especially trainers, for pretty much every possible occasion, but doing so carried far more high fashion cred than slipping into stilettos. Big brands like Chloé and Gucci began pouring their resources into creating the next and newest It trainer; meanwhile, gorpcore stalwarts such as Hoka and New Balance became regular fixtures on the street style scene. Wearing pumps out and about hasn’t become the wrong move, exactly, but it certainly hasn’t felt like the coolest of choices either.
But, to quote the great Bob Dylan: The times, they are a-changin’. Heels of all sorts strolled down influential Fall 2025 catwalks last February—Louis Vuitton, Prada, Valentino—and if this current season of shows is any indication, the trend is only picking up speed. Vertiginous footwear has been a theme at some of the buzziest new collections we’ve seen this month: towering, could-poke-your-eye out pointy toe styles at Khaite and Saint Laurent; sculptural-yet-sensual open-toe design at Fendi; ladylike gingham pumps at Dior. Meanwhile, there’s a vast and undeniably covetable selection of height-boosting footwear flooding the market right now, including several new(ish) comfort-focused shoe brands, like Inez and Nomasei, that purport to deliver heels with an optimal blend of Insta-ready aesthetics and foot-friendly function.
As someone who has always lived and died by adding three extra inches to her legs if she can, I’m thrilled by this sudden influx of options and the care put into them. But the idea that I might be able to wear tall, spindly shoes all day with the same ease as sporty lace-ups is both intriguing and foreign to me. As a person who professionally came up in the peak era of wearing heels to work (commute and all… the secret, my friends, is walk up stairs on the balls of your feet), I’m skilled in suffering for my art. It’s almost a point of pride.
Can I really enjoy my shoes of choice without a strict regime of Compeed, ice packs, and calf stretches? I decided to find out in the midst of a busy New York Fashion Week schedule and the spill over of events that followed. I tried six different styles from OG heel labels, legacy houses, and footwear newbies while running around all corners of the city to see which ones held up—and, for that matter, how I did as well. Here’s how it went.
#1: Marion Parke's Classic Slingback
Alison Syrett Cleary
Alison Syrett Cleary
The morning I planned to begin testing, I was running late with no idea as to what to wear, with two school drop offs and a full schedule of meetings ahead of me. Mercifully, though, Marion Parke’s chocolate brown suede slingbacks were a synergistic match for my one of my default fashion girlie outfits: baggy jeans and a vintage Fendi polo that never fails to make me feel like I’m going to hang out with some fabulous Euro heiresses in Monte Carlo. Marion Parke is named for its founder, a pediatric surgeon who works alongside master cobblers to create “original constructions that acknowledge the structure and function of the foot and ankle.” Every pair has a specially developed insole that’s sculpted to fit the natural contour of one’s foot; over time, it’s meant to mold to the wearer’s specific shape.
But what drew me to the line is how it doesn’t have the same orthopedic vibe most traditional “comfort first” heels have. Are all its promises too good to be true? I have a sneaking suspicion Parke may have not have factored in the degree of activity I had ahead of me, which includes traversing brownstone Brooklyn (with a three-year-old on my shoulders a good portion of the way), taking the train, and stomping through the cobblestone streets of TriBeCa. But I’m nothing if not a consummate reporter, so I slip them on and hope for the best.
Turns out, I don’t need optimism. I Iog roughly five miles in these mocha-toned babies, the majority of which are sensation free. At a few points in the day my toes do start to pinch a bit because of the triangular shape of the shoe and downward pitch of my foot. But for a pump that looks intimidatingly spindly and high, I’m impressed by how little the silhouette impacts my stride as I stomp through the city to meet with designers.
Heel height: 2.8 inches
My Score: 8.5/10
Marion Parke
#2: Nomasei's Gattaca Pumps
Alison Syrett Cleary
Call me an overachiever (or a masochist) but I decide to finish my day of Marion Parke with a night of Nomasei. The French It girl favorite brand—Suki Waterhouse, Lula Tung, and Bella Hadid are all fans—launched its very first stiletto heel, the Gattaca Pump, this past year with a promise that it’s comfortable enough to dance in. The proof is in its design: The shape, which includes supportive criss-cross ankle straps and a heel that sits at a slight inward angle, was based on a style that tango dancers use to perform.
I don’t have spicy partner dancing on the docket, but I am planning to take public transportation to a big party for Pandora jewelry. Honestly I can’t report much about the shoes because, well, I didn’t think about them or how they felt once after slipping them on. This is exactly what I want from my footwear, and it serves me especially well this particular evening as I meet up with a friend with whom I have juicy gossip to download on. And while I was originally planning to take a car home, I wind up hopping right back in the subway as my feet are feeling good enough to walk home from the station. The cherry on top: The next morning I receive a press release sharing that Pamela Anderson was at the same event in the same shoes. My only regret is that we did not cross paths in time for a photo op.
Heel height: 3.2 inches
My Score: 9.5/10
Alison Syrett
#3: Stuart Weitzman's Vinnie Zip Booties
Alison SyrettHeartened by all the new, foot-friendly options I've tried thus far, I decide to move onto an OG in the world of sexy, super desirable heels: Stuart Weitzman. The label has sent me what are essentially the bad b*tch ankle boots of my dreams, compete with towering 3.4 inch stiletto heels and lethally sharp toes. I’m immediately obsessed with how they make my legs look about a foot longer in jeans and decide that no matter how they feel, I’m in it to win it. Sometimes beauty is pain, right?
In this case, maybe just a little. Real talk: For the first 30 minutes of wearing these, I completely hate my life. With every step, my feet are pulsing and achy—from, I predict, being shoved in stiff leather cages after two straight summer months of broken-in sandals and canvas sneakers. I keep thinking about an episode of Friends in which Monica splurges on designer boots, but they are so excruciating that she rips them off and Chandler carries her home. Alas, no one is around to save me in the same way.
However, somewhere around the half hour mark, magic happens: my lower extremities seem to recalibrate to their new reality and the discomfort fully fades. I triumphantly continue on my day of press previews, including a stop by ALO where I try on a massive (faux) fur coat that seems to match the sassy personality of my booties. I’m obsessed with the jacket but even more so with the stompers, which I’m happy to report fully break in after three or fourmore wears. All the best things in life, after all, take a little work.
Heel heigh: 3.4 inches
My Score: 7/10
#4: Loewe's T-Bar Pump
Alison Syrett
“I’m texting my husband to make sure he’s there to receive my Loewe,” I say to someone at an event, as I type something to the effect of “You home? You can’t leave until my Loewe comes.” I look up and swivel my head around, looking for someone else to humble brag to. “I’m testing Loewe heels,” I say to no one in particular. “They are sending me a pair.”
Loewe, Loewe, Loewe! The thing is, they could send me tin cans to strap on my feet and I’d happily hoof around in them. The playful burgundy Mary Jane style pumps that do arrive, however, are far easier to style than aluminum soup receptacles. I pair them with a vintage Comme des Garçons wrap skirt and cropped T-shirt tie for a cocktail hour at the Jenni Kayne store, and subsequent drinks with a friend at La Mercerie.
I enjoy that these have a chunkier heel, which is far sturdier and thicker than most anything else I have tried thus far, with an excellent support-to-height ratio. My feet, in general, feel fantastic throughout the night, but the straps do cut into my ankles a bit. I imagine these would soften and mold to my body over time, but sadly I have to return the shoes before I get to find out. But, um… have I mentioned they were Loewe? So I’d probably still buy a pair if I had the cash for it.
Heel height: 3.5 inches
My Score: 7/10
#5: INEZ's Isa Mules
Alison Syrett
At this point in the week I am exhausted, and losing motivation regarding my wardrobe choices. And this particular morning all I really want to wear is a giant knit T-shirt from Coach, which I gussy up into an outfit with a leather mini skirt and slide-on heels from INEZ. (“It’s a bit ‘00s It girl walk of shame,” I write across a selfie in my stories. “But I’m making it work.”)
I have a bit of a bias with this INEZ: I’ve tried the label before and have been impressed with how well the shoes, which come in multiple widths and have cushioned insoles, hold up at parties. It does seem, though, that I’m adding an extra layer of difficulty by choosing a style sans ankle or heel strap—and wearing it for a day that includes two shows on opposite ends of Manhattan. This ante is upped when I manage to get both the time and location wrong for my first event. But the weather is nice and the slides are feeling good so I decide to walk…. and walk… and walk even more.
Roughly two miles later, I find myself at one of my favorite coffee shops. After a cappuccino refuel and bathroom break, I hoof it another mile or so to my next show after that.
Heel height: 2.8 inches
My Score: 9.5/10
#6: Reformation Slingback Heels
Alison SyrettAlison Syrett Cleary
Alison Syrett Cleary
A confession for you: Due to complications with product in stock and delivery times (I won’t bore you with the details), I am not able to get my hands on Reformation heels until after the fashion festivities wrapped in the Big Apple. However, the pair I had designs on trying are so break-my-heart cute that I extend my testing window a bit. To wit, I find myself packing these beauties a few weeks later for a quick trip across the country to The Broadmoor in Colorado Springs, aka the very first five-star resort in the world.
The good news is these turn every good outfit in my suitcase into a true fashion moment (I couple them with vintage Chloé trousers for lunch and a slinky Leo Lin slip dress at our last dinner on the property). Moreover, the stiletto factor is very manageable, and my heels and arches remain unaffected, even after an extensive post-meal tour of the hotel grounds. However, the sharply tapered shape of the toe does cut a bit into the side of my pinkies, and I now have the start of a blister on each. But do I fully, completely plan to wear them again? A lot? One thousand percent yes.
Heel height: 2.9 inches
My Score: 7/10
