Crush-Dressing: My Teenage Exploration of Gender Identity

FEATURE | STYLE

Written & illustrated by Tashi Donnelly (she/her) | @tashi_rd | Feature Editor 

When I was 13, I made some terrible hair decisions. After a string of different haircuts, bleaches and dyes, I ended up with a hideous, unsalvageable pinkish-red bob. The best course of action was to start from scratch. I signed up for Shave for a Cure, a fundraiser for Leukaemia & Blood Cancer New Zealand. After a few weeks of gathering sponsors, my step dad drove me down to the local hair salon, where I walked in and said, “Shave it all off”. 

With my new skinhead look, I leant into different styles. In my eyes, the bald head didn’t compliment my existing style. I had never dressed strictly femme, but now my pleated mini-skirts and floral dresses weren’t sitting right. Not to discourage anyone from rocking a smooth dome and girly fits, it’s a hot look. Something about being free from the confines of a “feminine hair-do” enlightened my still-developing prefrontal cortex to the concept of gender expression. However, in 2010, I had no idea what gender expression meant, or what I could do with it. I knew people called girls “tom-boys” and boys “camp” when they expressed themselves too overtly like the opposite gender. The concept of non-binary was floating around academic circles but hadn’t yet entered mainstream culture, at least not in my circles. 

One of my close school friends had a similar family dynamic to me; an absent father. Every year his dad would send him new sneakers, and because he didn’t bother to ask for his size, they were usually too small. While bonding over our father’s lack of interest in our lives, my friend offered me his collection of men's sneakers that didn't fit him. They were bulky high-top sneakers which were fashionable with teenage skater kids in the 2010s. This was my first step towards masculine apparel. With shoes like those I could take on the world, they made me feel confident and decidedly un-femme. 

The rest of my clothes didn't fit with these new shoes. When I paired them with fishnet tights and ripped-up denim shorts they looked like clown shoes. Things had to change. I took my brother's hand-me-down baggy jeans, long enough to cup the heel of my shoes, but tight enough at the waist that I wouldn’t be low-riding. My collection of oversized band tees expanded and I never tucked them into the pants. I acquired a few saggy beanies and baseball caps. “Borrowed” hoodies from my stepdad completed the look. Today, I wonder if some of the comfort I found in these clothes was related to my autistic sensory issues. Clothes that are too tight have always irritated me, tights caused constant itching and skinny jeans made me feel like my circulation was being cut off whenever I sat down. Nevertheless, donning this new attire made me feel free. Looking like the boys in class gave me confidence in a way I’d never known before. The lack of thought that went into dressing myself every day was a relief. I’d normally spend hours trying to match the bright colours, patterns, and varying shapes of my former eclectic wardrobe. Now, my whole closet consisted of baggy pieces in plain greys, blacks and muted colours. 

This new look did get me labelled by some as a dyke and a tom-boy. Gender and sexuality are separate concepts and experiences. These things are all interwoven, a complicated tapestry of identity that makes us all unique. But I’d be lying if I claimed this new experimentation with gender identity didn't open up Pandora’s gay box. I was adopting the familiar uniform of the boys my friends and I had crushes on. My best friend had a crush on the boy whose shoes I was now wearing. There was nothing weird about that. In hindsight, it feels like a complicated version of the classic lesbian dilemma: “Do I want to be her, or be with her”. Did I want to be a boy, or be the boy she would like?

Part of my cross-dressing era may have something to do with my best friend. I was now dressing like the grunge boys she had crushes on. We were those joined-at-the-hip besties, spending almost all our time together. Compared to the boys I liked, who I was so often too nervous to be myself around, she made me feel safe. When she complimented how I looked in my new style, I couldn’t get enough of it. I started taking note of which combinations she seemed to like more, which beanies she thought were cute, as I pined endlessly for her admiration. I enjoyed the newfound freedom of dressing like a boy, but now I desperately wanted to impress the girl I had a crush on… my best friend. 

It didn’t work, of course. I could never tell her how I felt, and I couldn’t cosplay my way into her affection. But I think about it often. Changing styles can be transformative. It can improve the way you perceive yourself, and the way you feel in your body. My gender stayed the same after that year, but my sexuality became clearer to me. As I got older I realised that clothes are overly gendered by society, and labels like “tom-boy” or “camp” were insulting descriptions to throw at people who didn’t conform. Yet, cross-dressing opened the door to understanding my bisexuality. Experimenting with gender expression helped me learn about my body and what clothes make me feel comfortable, even if it didn’t get me a girlfriend.