In 2012, Miuccia Prada sent a pair of Mary Janes down the runway so sweetly perverse that they sent a chill up my 21-year-old spine. While the design of the shoe itself—shiny black leather, with a heel arched like a back—was both elegant and exquisite, it was the final touch that thrilled me: The toe box appeared to be dipped in red latex.
Late last year, when I traveled to Milan for Prada’s spring 2025 show to cover the beauty backstage, my eyes began to wander during the encore walk, and ecco: My dream shoes—last seen on the fall 2012 ready-to-wear runway—were reborn. In fact, five different designs from the house (aside from my beloved Mary Janes, there were geek-chic sandals, pointy-toe heels, zippy kitten heels from 2008, and platform penny loafers from spring ’99) were given what Prada called the Re-Edition treatment in a show that paid tribute to Mrs. Prada’s idiosyncratic yet always spot-on style. Sadly, not all of them made it from the runway to real life—including my Mary Janes—which meant that, 12 years after I first put eyes on them, I would have to hunt down some of the originals if I wanted to have a pair of my own.
Wearing vintage—whether the so-called true vintage that’s more than 20 years old or a more recently minted find, maybe from resale sites like The RealReal—is clearly back on our collective mind. The vintage market has been growing by leaps and bounds in the last year, with reasons like sustainability and simply owning something unique being driving forces. Since buying a Lilli Ann coat from a store in Fort Worth, Texas, at age 15, I’ve amassed a closet (okay—two closets and three storage units) filled with carefully cataloged pieces. Each wrapped in pastel pink garment bags, the items include bespoke debutante dresses made to do the Texas dip in the 1950s, dozens of body-conscious Mugler originals from the ’90s, and yards of silky lingerie by Christian Dior. Vintage underwear? Of course—it looked just right under vintage garments (though the very notion startled my former editor Chioma Nnadi when I mentioned it to her). For me, wearing vintage has always been about a sense of individuality—and, yes, the satisfaction of saying “thanks, it’s vintage.” (Translation: No, you can’t buy this at any old store.)
Heading to lunch in a YSL Rive Gauche dress and another woman’s brassiere? Sure—hence my trousseau of conical bras, slip skirts, and garters—but I’ve long been skeptical of walking a single step in somebody else’s shoes. There’s a certain ick factor involved—theoretically, at least: A lingerie set, after all, can be sanitized in ultrahot water. Shoes, somehow, feel even more personal—after all, they literally mold to the shape of the foot of the person who wears them. Still, if I ever wanted to reunite with my dream Mary Janes, it was time to take a deep, cleansing breath and get over all of this.
“Shoes are the vintage category that gets the most physical wear and tear,” cautions Brit Blanco-Bird, the cofounder of the appointment-only vintage store Treasures of NYC—and who, tragically, hasn’t seen my beloved Mary Janes—as I start my hunt. Because shoes literally hit the pavement, they’re exposed to the elements in a way a dress or a handbag simply isn’t. That’s why finding vintage shoes in the like-new condition of so many dresses is unlikely.
Undeterred, I plow ahead—but wait, no, I’m distracted: There’s a pair of turquoise Giuseppe Zanotti butterfly heels that I swear I once saw on Sex and the City that make their way home with me, even though they look quite worse for wear. I reach out to Spasia Dimitrievska, the founder of online shop Fivedotsvintage, for some advice (after sorting out first that, no, she doesn’t have my Pradas either—ugh). “The first thing I do is check to see what can be fixed,” she says. “I always change the heel cap—that’s the most obvious sign that a shoe has been worn—and a good cobbler can fix small scratches. There’s a lot that can be salvaged.”
I send my newly beloved butterfly heels to midtown Manhattan’s Leather Spa—they recently repaired the Loewe Hammock bag that my 18-pound cat believed was his own vacation-style hammock—and they return patched, polished, and primed. (I also have my local cobbler replace the insole with something much more cushiony, and for a mere $17 I now feel like I’m floating on air, not tottering over West Village cobblestones in 20-year-old shoes.)
Dimitrievska cites slingbacks as one of the most in-demand styles from her shop, so I order two pairs rated “Excellent Condition” from The RealReal to see what the fuss is about—baby pink pointy-toes from Dolce Gabbana and a pair of black Chanels with a big pilgrim-like buckle. I’m drawn to both because of their sexy-prim designs, and find myself clacking around the office with glee.
I’ve also long been obsessed with practical, chunky-heeled oxford pumps from the 1940s, and hunt down a pair—only to place my foot inside and realize instantly that something was inexplicably wrong. Are these shoes haunted by the spirit of the plucky, practical gal who clomped around in them, ration tickets in hand—or is the arch simply in the wrong place for my foot? Either way: Back to the purveyor they go.
Were shoes simply made differently in earlier decades—or is this fit issue the same kind of thing one still navigates with sample sales and online binges? “The manufacturing of heels hasn’t changed much,” says Brynn Jones Saban, the owner of Los Angeles’s Aralda Vintage, “though modern-day heels can sometimes offer more comfort.” (Comfort, of course, being relative, with one person’s torture implement another person’s treasure.) Also worth noting: The pairs of Chanel, Fendi, Dior, and the like that have survived for decades in immaculate condition were perhaps considered special-occasion shoes at the time they were first purchased—not meant for, say, me to be running around Park Slope on a Tuesday.
As for my quest: Jones Saban recently sold a pair of Pradas (that and Ghesquière-era Balenciaga are her most desired gets) to a friend but, alas, doesn’t have the ones I’m looking for. And so, with my Prada search still at nada, I venture on to the vintage wild-wild-West site Poshmark, only to find my holy grails listed in my size, under $300, and with the rare, desirable label of NWOT—shopper slang for “new without tags.” If it all feels just too good to be true, I quickly realize it is: The seller hasn’t been active for over a year, and when I reach out with a quick “Is this still available?” message, it’s unanswered. A Poshmark spokesperson, meanwhile, tells me that only items selling for $500 or more are sent through the store’s authentication process, and that there’s not much that can be done about dormant sellers.
Still, I log on to Poshmark each morning, hoping against hope for a sign. My follow-up messages become more and more desperate, ending with a still-unanswered “I’ll give you double! Please!” Radio silence.
Will I ever know if this dreamy shoe fits? Hope springs eternal. In the meantime, I have five other pairs of new-to-me vintage shoes to wear while I continue to hunt.
