"How Can You Wear Those Heels?"
Posted: Mon Mar 30, 2026 10:55 am
While I was out and about on Saturday, I had a woman walk up to me and ask how I could stand in the four inch heels I was wearing. In all the years I've been publicly wearing women's clothing (close to twenty and counting), that's THE one question I've been asked most, especially by women who look perplexed, even awed at my accomplishment, as if what I did defied the laws of physics. My answer to her consisted of just one word: "Practice".
Being asked that question always makes me chuckle because it seems so silly to me. That leads me to suspect women believe men are inherently incapable of standing, much less walking in high heels, in THEIR shoes, and when they see men like me pulling off that feat, they have trouble accepting that reality. For me, it's no impossible task, I've been wearing heels since I was thirteen when I wore a pair of my mother's shoes to satisfy my curiosity over how she could walk in them. Once I discovered it wasn't all that hard (after some practice), it became great fun, and I've been strutting around in heels like in the picture below ever since.
Perhaps women who pose that question think men lack some genetic ability to master the feat of wearing heels, the simple truth isn't earth shattering: it's not that hard. Really. If women can do it, so can men. Plain and simple. That's the answer.
Being asked that question always makes me chuckle because it seems so silly to me. That leads me to suspect women believe men are inherently incapable of standing, much less walking in high heels, in THEIR shoes, and when they see men like me pulling off that feat, they have trouble accepting that reality. For me, it's no impossible task, I've been wearing heels since I was thirteen when I wore a pair of my mother's shoes to satisfy my curiosity over how she could walk in them. Once I discovered it wasn't all that hard (after some practice), it became great fun, and I've been strutting around in heels like in the picture below ever since.
Perhaps women who pose that question think men lack some genetic ability to master the feat of wearing heels, the simple truth isn't earth shattering: it's not that hard. Really. If women can do it, so can men. Plain and simple. That's the answer.
