Learning High Heels

By Monika Kowalska

The first time I slipped my feet into a pair of high heels, I felt like I had unlocked the final stage of femininity. Nevermind hormones, wardrobe upgrades or learning to wield eyeliner like a pro, this was it. I was ready to strut. Or so I thought.

What followed was not a clumsy struggle, but a deep admiration for women who seem to glide effortlessly in stilettos, as if high heels were an extension of their very being. I marveled at the way they moved, each step poised, each stride exuding confidence. My two cis female friends, who took it upon themselves to teach me, walked with such natural ease that it felt almost unfair. They didn’t just wear heels; they owned them. Meanwhile, I was still learning the delicate dance, trying to imitate their effortless grace. Their ability to balance elegance and comfort in sky-high shoes was nothing short of an art form and I wanted nothing more than to master it.

I practiced at home with the dedication of a scientist conducting a high-stakes experiment. I analyzed my posture in the mirror, adjusted my step length and even tried different flooring to simulate real-world conditions. My cat, unimpressed by my dedication, yawned through the whole process. I added music to the equation, trying to find the perfect rhythm that would trick my body into moving smoothly. Slowly but surely, my steps became less mechanical, my balance more natural. High heels were starting to feel less like a threat and more like an extension of myself.

My love affair with heels, however, didn’t begin with my transition. As a child, whenever my parents were away I would sneak into my mother’s closet and slip into her stilettos marveling at the way they made me feel. Of course, back then my steps were even clumsie and my biggest concern was making sure I put them back exactly where I found them so she wouldn’t notice. But the thrill of those stolen moments stayed with me, a secret longing I carried until I could finally embrace heels as part of my own journey.

Then came the big test: wearing heels in public. The grocery store seemed like a safe bet, smooth floors, shopping carts to hold onto, and minimal judgment (or so I thought). It took approximately three steps for me to realize the floor was actually a waxed death trap. The moment I let go of my cart, I wobbled like a newborn foal bumping into shelves and nearly knocking over a pyramid of canned beans. A kind elderly lady asked if I needed help probably mistaking me for someone recovering from anesthesia.

But I refused to give up. I learned to take smaller steps, lean back slightly and most importantly, fake confidence. Because here’s the secret: no one questions you if you look like you know what you’re doing. Even if your ankles are screaming in protest.

High heels today come in a dizzying array of styles, wedges, kitten heels, block heels, slingbacks, backless heels and more, each designed to suit different tastes and levels of bravery. However, I noticed that most of my female friends tend to wear heels less frequently opting for something more comfortable for everyday life. Of course, official events, parties and weddings are still sacred ground for stilettos, but for casual outings many women prefer the sweet relief of flats or sneakers.

After weeks of practice, I finally managed a proper high-heeled strut. Was I as graceful as a Parisian runway model? Absolutely not. Did I stop fearing for my life with every step? Mostly. But when I finally clicked my way across a room without gripping the nearest object for stability, I knew I had arrived. High heels, you may have won the first few battles, but I won the war.

And along the way, I learned a crucial survival tactic: always keep a pair of sneakers in the car for emergency heel relief while driving. Because while I might have conquered walking in stilettos, driving in them is a whole other nightmare.

Since 2013, Monika has been interviewing trans people in her blog, The Heroines of My Life. Click here to see who she has interviewed lately.

Wearing Ann Taylor

Alan Cumming and friends femulating in British television’s The Runaway.