These Shoes Made Me Believe in Comfy High Heels

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In the mid 2000s, when I was in my twenties and pointy-toed, high-heeled boots were all the rage, I wore a pair on an international flight from Germany to the U.S., navigating through airport terminals and long queues with nary a hobble. This is also around the time in my life when several of my friends got married, and I danced the night away in stilettos at wedding receptions without a second thought. Despite all this, my back did not hurt. My head did not ache. My feet did not swell. Those things were not a thing when I was young.

Now that I’ve reached my mid-forties, though, something wildly unfair has happened: I still love my high heels as much as ever, but they most definitely do not love me back. Within an hour of putting them on, I’m ready to take them off. I stand in my closet, gazing wistfully at the shoe collection I’ve so carefully curated, now gathering dust because they hurt my feet. It’s like when you feel like you should be driving a cute sports car, but deep down, you have to grudgingly admit to yourself that you’ve crossed into your minivan era.

Still, I’m not ready to trade in my sexy shoes for some sort of dowdy slip-ons just because they’re more comfortable. I’m not a flats girl, and loafers are a hard no for me. So I’ve spent the better part of the last couple of years searching for a shoe that combines the best of both worlds: the sexy silhouette of a stiletto with the cushy feel of something that’s … well, not a stiletto.

I’ve tried Naturalizer shoes before; I have the Baylor heels, and I do like them — they get my seal of approval. But their heel is a smidge wider than a traditional stiletto, which makes them feel not quite right to me. So when I came across the Jackie Sandal Stiletto from Antonia Saint NY, I was eager to try it out — because they have the look of an actual stiletto but, according to the company, an unparalleled level of comfort. And when I got an invitation to an evening with friends at an “upscale casual” restaurant and bar, I had the perfect opportunity to take these babies for a test drive.

Here was my “lewk,” as the kids say, for the occasion … don’t judge the spots on my mirror or the dog toy on my bed, OK? (And in case you’re curious, my tank is actually from Market & Spruce — it’s old and I believe it’s discontinued, but there are some almost exactly like it on Amazon. My jeans are the Kut from the Kloth Katy Boyfriend Jean, which I think are the perfect length to wear with heels.)

When I say I gave these shoes a test drive, I mean it. I wore them around my house for more than an hour before ever stepping foot outside — because sitting down at dinner isn’t exactly the most rigorous test of a shoe’s comfort level (although if I have even one sip of a martini, my feet swell even if I’m doing absolutely nothing, so there’s that).

Lo and behold, besides being cute, they were actually comfortable. My feet felt supported but not squeezed; my toes didn’t feel crunched. The straps actually have a little padding to them, which keeps them from digging in. There is plenty of cushion under both the heels and the balls of the feet, those pressure points that are usually the first places to hurt. That’s the SoftSurround System, which the company describes as “created to surround the entire foot, from top to bottom, with a 360-degree envelope of cushioned comfort.”

As a bonus, these shoes have a ballistic nylon heel (yes, really!) that keeps them from getting nicked — and as someone who once cried for half an hour because I nicked the heel of a pair of Christian Louboutins, that’s a small-but-important detail.

My one teeny gripe with these heels was that, until I got used to the sensation, the seam of the padded part felt like I had something underneath my toes (technically, I guess I did, but I mean for a while it felt like something that wasn’t supposed to be there). Kind of like when you wear, say, a ring on a different finger than usual and it feels weird for a bit. But that went away soon enough, so it wasn’t a big deal overall.

The verdict: Antonia Saint NY makes a solid heel that is both legitimately cute and comfy — a combo that’s really hard to find. I did not feel like I was sacrificing style for comfort, and they’re equally perfect for a night out or a day at the office. As I’ve only had mine for a couple of weeks, I can’t speak to the durability, which is one reason I also can’t definitively tell you yet whether they’re worth the money; at their typical price, they’re $285, not exactly pocket change for most of us (although they are a whopping 50 percent off at the moment, which means now is the time to buy, no matter what). If they’re as comfortable as they are and as cute as they are AND hold up to wear and tear, they’re definitely worth every penny of the full price in my opinion. I’ll update once I’ve had mine longer.

Do they feel like sneakers? Nah. They’re heels. I don’t come home from running errands and slip into my Antonia Saints. But as heels go, these are some of the most comfortable I’ve found — and they don’t look like they belong in my grandma’s closet.