You’re ugly and your mother dresses you funny.

I am finally coming out of the closet. Not that one. I’ve been out of that one since I was 18. I’m talking about my clothes closet. My wardrobe. Interesting word “wardrobe,” meaning both a piece of furniture that holds clothing and the outfits themselves. Well, my wardrobe feels like a prison and I can’t stand it anymore. I keep brushing up against hastily purchased items — a silver blouse, some velvet pants. I think I just tripped over a pair of sensible pumps. Are those really mine? How did this happen?

I blame my mother. That’s fair, right? I first saw myself reflected in my mother’s eyes: a blurry, girl-shaped image filtered through her vision of what I was to become. Parents do this. They create a mental picture of who their adult children will be. The templates we daughters are expected to conform to are mostly the same.

Is she kind? Check. Caring? Check. Sugar and spice and everything nice? Check, check and check. So far, so good. My template was not too constrictive. My mother is sporty and so am I. My mother likes to dress in casual clothes most of the time. Awesome! Me too! My mother is straight and has been married to my father since 1966, er… uh… hmm…. (If we don’t draw attention to that one, maybe no one will notice). When my mother dresses up she wears skirts and dresses and heels and makeup and sometimes even curls her hair! What? I think we have a problem now.

I don’t see myself as my mother sees me. For her, and for most of our culture, the clothing part is the easy part. When girls dress up they wear skirts and dresses and (apparently) they like it. Styles vary, but the gender signifiers of the clothing are quite clear. When I see myself reflected in the mirror in an outfit like that, it makes me queasy and anxious because the image I see reflected doesn’t match the way I feel. And it’s not that I don’t feel female, but I have never felt feminine. This has been a source of frustration and despair for my mother and for me.

There were times growing up when I donned some fancy duds, looked in the mirror and liked what I saw. But the clothes I was wearing on those occasions were not the clothes my mother wanted me to wear to large family gatherings. I wanted to dress like my dad. You see, when I was a little girl, my dad taught me how to tie a necktie. He taught my brother and me both how to tie his favourite knot, the Half Windsor, and I loved to practise it. My dad had so many great and colourful ties to choose from — it was the ’70s, after all. He also had a fantastic hat collection: fedoras, bowlers, Irish caps. I loved dressing up like him then surprising myself in the mirror, catching a glimpse of the boyish spirit that lurked inside.

As I grew a bit older, my necktie-tying skills came in handy for certain events, like Casino Night in high school. My friends would wear very becoming, tight-fitting flapper dresses with rows of swinging fringe and knotted ropes of fake pearls. I would get my dad’s white tuxedo jacket out of its thin plastic dry-cleaning bag, grab his fedora from the top shelf and knot up a stylish tie. I swaggered in that outfit.

And there was the time when I was working as a lifeguard at Girl Guide camp and the staff reenacted Prince Andrew and Fergie’s wedding. I was Prince Edward in a borrowed military uniform jacket, shirt, hat and tie. (Our “Prince Andrew” came out a few years later, around the same time I did.) I couldn’t stop looking at myself in the mirror. I felt so good, so sharp.

But those were costumes, right? That wasn’t how I was supposed to dress. For celebrations, girls wore fancy girly clothes and might (oh please, please!) get away with dress pants and a blouse. I accepted this. Resigned myself to it, I suppose. I saw no alternative on television, in the movies, in the myriad images of “female” that had swirled around me like amniotic fluid since my egress from the actual womb.

So I had a wardrobe of acceptable (to me and to my mother and therefore the rest of society) unisex clothing: pants and shirts loose enough to disguise any overtly feminine features, sweaters and sport-specific clothing, outdoor wear and a few grudgingly purchased “good” clothes: a skirt, a few blouses, two pairs of dress pants, no dresses, one pair of dusty heels. At every wedding or shower or royal ball, I looked like a secretary who had come straight from work. Fully aware of my inadequate wardrobe, I wore my discomfort like a puss-filled zit. But it didn’t stop people from complimenting me on how nice I looked. Applauding my effort: “All she needs is a little encouragement.”

I’ll tell you this right now: I’m cheap. Anytime I have to spend money on something I don’t like, I get very grumpy. I can still feel the pain of every penny spent on an outfit I purchased because I thought I had to. Why is it that a woman is expected to show up in a totally new outfit to every social event when a man can get by for years with a couple of suits?

The beloved sweater vest!

Ranting about this to a friend of mine a few years ago she said, “Why don’t you get yourself a nice tailored suit?” To be honest, I’d never really considered it. I think at the time I eschewed the idea as too expensive and over the top, but somewhere inside me the idea stuck.

My journey out of the sartorial doldrums began two years ago with a necktie. Faced with yet another Xmas party where all the women had bought new dresses — “even fancier than last year’s” — I decided to do something different. It was a party full of actors and musicians, so I felt freer to experiment.

I did it: I crossed the aisle, I headed to the men’s formal section and found a purple-and-cream tie, which I paired with a shirt with French cuffs. Success! My tie was drooled over by men and women alike that night, and I felt good. I got my Casino Night swagger back. This time I believed the compliments.

I later matched the tie with a simple black V-neck sweater and wore it to a work conference. Again the compliments; again the swagger.

Finally, last year, I bought a suit, an off-white vest and pants. It was from the women’s section at H&M and it felt like the perfect mix of fit and line. And I bought a vintage tie. Actually, I had bought the tie first. This was becoming a pattern for me. I found this great tie and knew I needed the right thing to wear it with. I bought the suit to match the tie and when I put them on and looked in the mirror I felt good. A hint of feminine mixed in with the masculine. I felt dapper and suave.

I began to search through vintage stores to find ties I liked, early1960s skinny ones, mainly. My wardrobe began to change. I began to enjoy matching my ties with dress shirts and argyle sweater vests or slim-fitting cardigans. And the more I dressed “like a boy” the more the girls began to notice. All the girls — even straight girls. It was amazing. They looked at me and smiled in this very interesting way, like they were attracted but surprised at the same time. It was so hot. I gained a confidence I had never before possessed. I felt sexy. I had never, ever felt sexy.

Now when I look in the mirror, dressed in my finest threads, I like what I see. And the more confidence I gain, the easier it is to ignore the shadow of disapproval I still see reflected on my mother’s face. It took me a long time to realize that I was free to make this choice — to choose my happiness over someone else’s. To show on the outside what I feel on the inside.

I am 41 years old, and I’m not going to let my mother dress me anymore.

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This piece was originally published online by the well-dressed folks at DapperQ.

Titus Androgynous is a performer, graphic designer, boxer and, evidently, a writer. She lives in Toronto and is refashioning the casual Canadian dress code with her dapper aesthetic.