Growing up I loved getting dressed. More so than getting dressed, I loved watching my mother get ready for various parties and outings. She wasn’t inclined to wear the latest fashion and was a pro at finding deals. My mother took pride in looking her best. She was a natural beauty who grew up in the South, an army brat who attended church regularly—in the South putting on your Sunday best was paramount, especially within the Black community.
I would sit on the lip of the tub in my parent’s bathroom and watch her apply her makeup and do her hair step-by-step. I would watch as she curled her bangs in a studied and concise manner, applied lip liner without leaving a smudge of imperfection, and lined her eyes with kohl eyeliner without so much as a single tear falling. Once her face was done up and her hair was pristine, she would enter her walk-in closet just off the bathroom and select her outfit; she always started with her shoes.
From an early age my parents allowed me to pick out my own clothes, down to my shoes. Among my most coveted pairs were Vans in elementary school, Converse in middle school, and Louis Vuitton moccasins in high school (gifted to me by a friend’s mom who worked for the company). Shoes were definitively male or female, at least at the time. As I found myself and my gender identity, footwear would guide me. My mother’s closet was my entry point.
In my earlier years my mom worked in investment banking, an industry fueled by wealth and the male ego. I always admired that throughout this her style remained feminine and maybe even became more so. Her go-to shoes were Ferragamo ballet flats or lower heels by Via Spiga that had a cork heel and platform and maroon patent-leather upper and straps. (This pair in particular I would try on when no one was home.)
I told my mother once that I was a girl when I was six years old, something I don’t think anyone who knew me would be surprised by, even her. My mother told me, matter-of-fact, that I was male and it could not and would not change. It was a one-and-done conversation, I remember. I didn’t feel ashamed, but I knew not to mention it publicly.
I had no reference to pull from, no one else to use as a guide on how this should be brought up and how it could possibly go. I am still grateful to this day that I had a much more pleasant experience than many other trans people have had coming out to their families. Nonetheless I knew my confession didn’t feel exactly right. So like most trans women in their youth, I learned to express my gender identity privately. I always knew that I identified as female, a girl, a woman, because it was so early and innate and certainly not due to my environment or the way I was raised.
I wanted to be liked, and I wanted to look good and be courted romantically and be pushed on the swing in the same way girls were. I wanted the distinct femininity that came with girlhood but didn’t have the language or means to express that. So when I was told that I wasn’t a girl in black-and-white terms, I chose to push that part of myself deep into a place no one could see it. This was the ’90s, and homosexuality was becoming mainstream with prime-time shows like Queer Eye and Will Grace. Taking cues from the people around me and the media at the time, I quote-unquote chose to be gay. That was more palatable, an easier way to live or at least get by. Yet whenever I was left to my own devices or could sneak upstairs away from prying eyes, I would slink into my mother’s walk-in closet, slipping my feet into heels from Prada and Manolo Blahnik. I felt like Carrie Bradshaw in Sex and the City, a show I’d absorbed by lingering in the room as my mom and aunts would watch.
In the late ’90s and early aughts, I saw certain patterns with these women onscreen and their brand loyalties. Manolo Blahniks were for polished metropolitan women with exciting lives and day planners; they drank martinis without wincing. Prada was for the power woman; she was a boss, and all the women in my mother’s office wore them in various heights and colors. I wanted to be exactly like those women and the women I knew in my life; I wanted to have a career (something in the arts, but I didn’t know what at the time), I wanted to date dashing, funny men and have a group of girlfriends to go to parties with.
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As time went by and I got older, my family and I moved from the easy breezy-ness of California to the east coast of New Jersey, where both my parents would commute to New York City. It was an intimidating metropolis to me at the time. With such proximity to the city in the 2000s and nearing the early 2010s, I was certainly more exposed to not only an array of open gender expression but also a cornucopia of designer shoes: Marc Jacobs, Miu Miu, Dior by John Galliano. It was truly like being a kid in a candy store!
I still remember my first trip to Marc Jacobs in SoHo during my junior year of high school. (Incidentally Judith Light would be the one to provide directions; she was on Ugly Betty at the time and coincidentally played the mother of a transgender woman.) All the sales associates were androgynous and painfully stylish. Miu Miu had recently shuttered menswear, and while I was disappointed about that, it was still the stop I was most looking forward to. There I would be able to watch my mother try on a collection in the jewel box of a shop. Coats were thick and candy-colored, heels bejeweled, and sunglasses retro and huge—the look du jour in the early aughts when Nicole Richie and Lindsay Lohan were making headlines and consistently on the cover of tabloids. Miu Miu was the most distinctly feminine brand, and without a doubt I knew that one day I would wear it.
Men’s D&G shoes and Christian Louboutin loafers with Ferrari-red soles brought me closer to the person I wanted to be. Baby, you couldn’t tell me a thing as I walked in these covetable designer shoes. Even though they made my feet swell, they gave me a swagger you couldn’t easily wipe off and the confidence to accompany it.
Fast forward to an almost post-pandemic era and true adulthood: I had a newly cemented life in New York and a career in fashion working for a creative director I’d admired since my teenage years, and off the heels, pardon the pun, of a fresh breakup, I was ready to be me, fully. I had started my physical transition after a few months of a social transition, and everyone was acclimating to the autonomous young woman I’d grown into. I knew straight away that my very first pair of heels would be by Miuccia Prada. It was time for me to return to Miu Miu. It was a no-brainer. I needed my training wheels to be these chic and Italian “click-clackers,” as my friends and I affectionately referred to them. I settled on a pair of kitten heels that worked for both the office and nights out. They were black, patent-leather Mary Janes, and I wore them down to the nub—literally. I wore them until the screw that held the structure of the heel punched through the bottom.
Then I discovered that Manolo Blahnik made shoes for a size 12 (the cutoff for many designers) that fit comfortably. Shortly after discovering this, I started a job that had a fashion closet. At the end of each season, the closet would be filled with clothes either purchased by the company or not returned to the PR companies and designer showrooms. On a relatively slow day, as I sat at my desk, a key was dropped in front of me. I was told to have at it, with a wink and a smile, by a coworker. I giddily but calmly walked into the closet that was set up not unlike my mother’s.
The very first thing I noticed was the unmistakable white box with simple black lettering. I told myself not to get excited as a size 12 shoe isn’t as common as one would hope, but to my surprise there was a pair of midsize silver strapped sandals by Manolo Blahnik. I didn’t give it a second thought; they were mine. That kicked off a love affair I’m sure will last me the rest of my life. (You’ll rarely find me in a flat unless they’re Chanel or a boot.) I’d read that Tina Chow solely wore Manolo Blahnik, and I know he’s Rihanna’s shoe designer of choice. I’ve worn Manolo Blahniks on first dates and probably wore them during breakups too. I collected so many pairs at this point that my boyfriend has started to make mention of them taking over my room, spilling out from underneath my bed where I keep them. They’re perfect shoes for stepping into a more social existence, navigating a life where I finally presented as myself—now and forever.