I’ll admit it: I’m someone whose personal style tends toward minimal, classic, and cerebral—cough, boring—rather than, say, daring, bold, or cool. That has never bothered me…until a few weeks ago when I was getting dressed for a friend’s 30th birthday party and, confounded by shoe options, asked myself: Must it always be the same loafers and pointy-toe sock boots?
I reluctantly wore my loafers anyway, but found myself wondering if I was in shoe purgatory. Lost in thought, I stepped into a slushy pile of gray snow en route to the restaurant. Ew. Then, a revelation: If everything is going to get ruined anyway, shouldn’t I at least have a little more fun?
By that, I mean harnessing “main character” fashion energy—but letting my choice of shoe take the lead. I love whimsy, and I’ve always believed that impracticality is a form of luxury…so why not wear a pair of chartreuse velvet ballet flats in the dead of winter? Maybe, I hypothesized, the choice would have less to do with looking cool and more about how a pair of shoes could make me feel.
New York Fashion Week was quickly approaching, and I had events, dinners, previews, and shows lined up for nearly a week straight—surely I could muster up the courage to be daring. Enter my sherpas: Mandy Lee, TikTok’s preeminent “freaky shoe” expert, and Sabrina Elba, whose sexy spin on minimalism reads to me, in all caps, MAIN CHARACTER. I fired off an SOS text to them both. “My advice is not to try so hard,” Lee replied by voice note. “Switch your mindset to think about shoes as joy-procuring objects, not something you must wear to protect your feet. That’s where the magic happens.” Elba offered: “If your shoes make you feel a little bit powerful and a little bit mischievous, you’re on the right track.”
The first test was a Fashion Week Super Bowl party at the Whitby Hotel. I swapped my tassel loafers from The Row for a sculptural, architectural kitten heel from Proenza Schouler and, flopping into bed at the end of the night, I wrote myself a note: “Sorry, that was the chicest fucking outfit. I’m so glad I went with the Proenzas??? Really, really, really glad!!!! Wooo!!!!!”
That’s what joy feels like, and it was my first data point: A main-character shoe doesn’t have to be loud—it just needs to feel a little more me.
For a Wuthering Heights screening a few days later, I picked a rarely worn pair of The Row gold lamé glove flats and felt mischievous the second I slid them on. Their ultrathin construction was wildly impractical for the walk between dinner and the theater—one wrong step and my night could be over—but the flats made it home unscathed (and if something bad had happened, I realized, I wouldn’t have minded).
As Fashion Week came to a close, I realized that I wouldn’t actually know if my shoe experiment succeeded unless I stepped far outside my comfort zone. I needed to try on the kinds of bold, canonically main-character shoes I’d never venture to actually own. So—twist my arm—I made a trek to Bergdorf Goodman’s shoe floor on Saturday afternoon.
I didn’t have an agenda, but I zeroed in on Nina Christen’s furry ankle booties (wishing I had somewhere to après); sky-high platform snake-print pumps from Chloé (I’ll never confidently walk in these); sexy satin Saint Laurent kitten-heel slingbacks with their signature ultrapointy toes (naughty!—but a want, not a need); and a wild pair of Manolo Blahnik pumps with a patchwork of animal prints (cheetah, zebra, giraffe?), all in ponyskin (intriguing, but ultimately not me).
As I walked out of Bergdorf’s with no new shoes in tow, I decided that my experiment hadn’t turned me into a new person—or made me want to blow up my closet and start over. Instead, as I considered actually buying each pair, I found I could tell the difference between what would be mischievous and what would feel like I was trying. Saying “no” didn’t feel like fear—it felt like choice.
I caught my reflection in the storefront glass as I began my walk home. I was in my standard uniform: baseball hat, green suede Dries Van Noten bowling sneakers, jeans a touch too long and damp at the hem. On my face, I wore a grin that reached the corners of my eyes.
It turns out that—all week long, a little at a time—shoes had brought me back to myself. If that’s not main-character energy, I don’t know what is.
In this story: Hair, E. Williams; makeup, Grace Ahn; manicures, Naomi Yasuda; tailor, Cha Cha Zutic.
Produced by The Morrison Group. Special Thanks: Waldorf Astoria New York.