I’ll admit it: my personal style leans toward minimal, classic, and cerebral—okay, maybe a little boring—rather than daring, bold, or cool. That never bothered me… until a few weeks ago, when I was getting ready for a friend’s 30th birthday party. Staring at my shoe options, I wondered: Does it always have to be the same loafers or pointy-toe sock boots?
I ended up wearing the loafers anyway, but I couldn’t shake the feeling that I was stuck in shoe purgatory. Lost in thought on the way to the restaurant, I stepped right into a slushy pile of gray snow. Gross. And then it hit me: If everything’s just going to get ruined anyway, shouldn’t I at least have a little more fun?
What I mean is tapping into that “main character” fashion energy—but letting my shoes lead the way. I love whimsy, and I’ve always believed that impracticality is a kind of luxury… so why not wear chartreuse velvet ballet flats in the dead of winter? Maybe, I thought, it’s less about looking cool and more about how a pair of shoes can make you feel.
New York Fashion Week was coming up, and I had events, dinners, previews, and shows lined up for almost a week straight—surely I could find the courage to be a little daring. Enter my guides: Mandy Lee, TikTok’s go-to “freaky shoe” expert, and Sabrina Elba, whose sexy take on minimalism screams MAIN CHARACTER to me. I sent them both an SOS text.
“My advice is not to try so hard,” Lee replied in a voice note. “Switch your mindset to think of shoes as joy-bringing objects, not just something you wear to protect your feet. That’s where the magic happens.” Elba added: “If your shoes make you feel a little powerful and a little mischievous, you’re on the right track.”
The first test was a Fashion Week Super Bowl party at the Whitby Hotel. I swapped my usual tassel loafers from The Row for a sculptural, architectural kitten heel from Proenza Schouler. Flopping into bed that night, I wrote myself a note: “Sorry, but 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 lesson: A main-character shoe doesn’t have to be loud. It just has to feel a little more like me.
A few days later, for a Wuthering Heights screening, I chose a rarely worn pair of gold lamé glove flats from The Row. I felt mischievous the moment I slipped them on. They were wildly impractical for walking between dinner and the theater—one wrong step and my night could’ve been over—but they made it home unscathed (and I realized that if something bad had happened, I wouldn’t have minded).
As Fashion Week wrapped up, I knew I wouldn’t really know if my shoe experiment worked unless I stepped far outside my comfort zone. I needed to try on the kind of bold, quintessentially main-character shoes I’d never actually buy. So—twist my arm—I made a trip to Bergdorf Goodman’s shoe floor on Saturday afternoon.
I didn’t have a plan, but I was drawn to Nina Christen’s furry ankle booties (wishing I had somewhere to après-ski); sky-high platform snake-print pumps from Chloé (I’d never walk confidently in these); sexy satin Saint Laurent kitten-heel slingbacks with their signature pointy toes (naughty!—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 not really me).
I walked out of Bergdorf’s empty-handed, realizing 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 buying each pair, I could tell the difference between what would feel mischievous and what would feel like I was trying too hard. Saying “no” didn’t feel like fear—it felt like a choice.
I caught my reflection in the storefront glass as I started walking home. I was in my standa—My everyday look: a baseball cap, green suede Dries Van Noten bowling sneakers, and jeans that were a bit too long, damp at the hem. On my face, a smile that reached my eyes.
It turns out that—all week long, little by little—shoes had brought me back to myself. If that’s not main-character energy, I don’t know what is.
In this story: Hair by E. Williams; makeup by Grace Ahn; manicures by Naomi Yasuda; tailoring by Cha Cha Zutic.
Produced by The Morrison Group. Special thanks to the Waldorf Astoria New York.
Frequently Asked Questions
Of course Here is a list of FAQs about In Search of the Perfect Shoe designed to sound like questions from real people
General Beginner Questions
Q What does the perfect shoe even mean
A Its not one magical shoe Its the right shoe for youconsidering your foot shape activity comfort needs and personal style Its the shoe that supports you without causing pain
Q Why cant I just buy shoes that look good
A You can but prioritizing looks over fit often leads to blisters foot pain and longterm issues like bunions or plantar fasciitis The goal is to find a shoe thats both stylish and supportive for your body
Q How often should I replace my everyday shoes
A A good rule of thumb is every 300500 miles of walking or every 612 months for daily wear Check the soles and midsolesif theyre worn down or no longer springy its time for a new pair
Q Wheres the best place to get my feet measured
A A specialty running store or a good shoe store with trained fitters is ideal They measure both length and width often while youre standing and can analyze your gait
Fit Comfort Questions
Q How much room should be in the toe of my shoe
A You should have about a thumbs width of space between your longest toe and the end of the shoe Your toes should never feel cramped or pushed against the front
Q My feet are two different sizes What do I do
A Always fit the larger foot You can use an insole or heel pad to adjust the fit for the smaller foot Some brands also offer splitsize purchasing
Q Why do my shoes hurt even though theyre the right size
A Size is just one factor The shoe might be the wrong shape for your foot or it might not have the right support for your activity The breakin period shouldnt be painful
Q Are breaking in shoes a real thing
A Shoes should feel comfortable from the first wear A little flexibility adjustment is normal but true