I returned to my Milan apartment to be greeted by a thick Spanish accent, “ohhh … Alexander McQueen,” gushed my flat-mate, “I love dat fragrance.” He was tall, dark, handsome, Paraguayan, and fabulous. Flavio — much like Cher — was known in the nightclub circuit by first name only. He was also famous (in more intimate circles) for sizzling up personal platters of spaghetti alla carbonaraat 4 a.m. in nothing but a white robe — lit Marlboro Light in hand. His signature pasta ended up sprinkled with ash before reaching its final resting place: a watery grave of partially digested negroni.

Flavio and I got on quite well. Despite being at odds on both the gender and sexuality spectrums, we balanced each other perfectly. When our toilette broke, he would head out toward the city center, wrapped in a chic trench and Burberry scarf — all a ploy to hijack the “facilities” at La Rinascente without being detected (a move I coined at Bloomindales back in the states). Flavio was stylish and good-looking, but in my mind, he was only able to pull off such a unique brand of un-ladylike behavior for one reason: biologically he was a man. As a woman, I felt pressure to repress my inner man-child (a version of whom I would later marry — a separate tale entirely).

When I moved from Milan to New York, I brought only a single suitcase. Among my most prized possessions: a men’s size small European-style bathing suit. In my experience, the fibers that make up most women’s swimsuit bottoms had an uncanny knack for sensing the most unfortunate moment to “rally the troops” on a unified march straight up my ass. The boy-shorts I’d picked up overseas paired well with a black bikini top — and were the first swimsuit bottoms I had ever owned with the staying power my kind of day at the beach required, i.e. serious frolicking and, on occasion, bending over to sculpt the likes of a curled up dog or a functional sand toilet.

The swimsuit, like the fragrance (and, well, the sand toilet), was an early step in a quest to self-express. I aimed to do this outwardly by developing a signature look, which I like to call: soft-core cross-dressing. The ability to determine which pieces of a lady’s wardrobe can be purchased in the men’s section is something of an acquired proficiency — a true craft that I spent years honing on the streets of lower Manhattan. I took style cues from a seemingly endless trickle of tall, slender, effeminate men whose artfully messy ponytails swished back and forth on Crosby Street; their Rick Owens leather styled with denim — the good kind that, unbeknownst to most, is finished with some type of formaldehyde.

A general rule of thumb I picked up for a non-gender-bending dalliance in the wares of the opposite sex: avoid overtly feminine or masculine pieces. Opt instead for those that fall within a cultural frame of reference, and re-imagine them in a modern way. For instance, I might pick up a V-neck cardigan with suede elbow patches to pair with a narrow pant, an oversized raglan-sleeved crewneck jumper, or a bowler’s hat (a la the famous Milan Kundera novel). Sure, I received some less than complimentary comments from other straight females, e.g. “you’re going to wear that?” And admittedly, I’ve made some heavy missteps along the way — most notably a pair of board shorts that will live on in digital perpetuity as a reminder that I was the lucky recipient of my father’s waistline.

On a recent trip to Germany, my unisex pride reached a real culmination. I was standing in line at a dance club on the outskirts of Berlin, my long hair unwashed, wearing a snug motorcycle jacket with skinny gray jeans — rolled up to reveal a pair of desert boots and two unshaven ankles. And that’s when I realized: I look like a German man. Had I still smoked, a cigarette would have dropped right out of my mouth. It was this precise moment that I began to understand who I was. After spending almost the entire decade prior trying to look attractive to men, at some point in my mid-twenties, I realized intellect was a much better editor than a pair of heels and a push-up bra. If my thoughts alone didn’t repel him, he stood half a chance.

Even more importantly, I knew that I no longer wanted to be a passive consumer of culture, to drink the Harper’s Bazaar Kool-Aid season after season. Through dress, I had a voice to assert my own take on womanhood: that being a female need not define your role in society. While our culture’s current gender binary does nothing to promote the true self, it does give us a box to break out of — if we want to. Still, gender may predict more than any of us are willing to admit. For instance, I still love the Alexander McQueen fragrance I picked out that day in Milan. However, I remain disappointed to have learned from Flavio that, in fact, I’d purchased his favorite women’s perfume.