I’ve always loved dressing up. I love Halloween, and when I was working in a primary school I took my various fancy dress days very seriously. Always the first into the makeup jar. I loved to pretend - to be anyone else, anywhere else. But when I transitioned, I found the whole prospect frightening.
I can’t articulate exactly what I found difficult. The whole thing just became daunting. My biggest inspirations were mostly women; teachers from my childhood that showed up as skeletons, ghosts, and devils. Cats and death. Witches, good and bad. Fellow teachers I worked with would dress up as book characters regardless of gender; I’ve seen my share of ladies dressed up as Roald Dahl’s BFG. I’ve been using their examples most of my life, so I wasn’t worried about meeting gender expectations.
"IT’S AN ATTITUDE THAT I HADN’T QUITE GRASPED, EVEN AS I UNDERSTOOD IT."
However, there are subtle considerations that change how one dresses up. Hair being a huge one. Suddenly I had hair to style, but couldn't do a great deal with on account of my fear of showing the edges of the wig. Also, the way women do a devil isn’t the same as the way men do it - and it’s not just about being sexier or something. It’s an attitude that I hadn’t quite grasped, even as I understood it.
When I say I understood it, I mean on a visceral level that borders on primal. I knew what to do, even if I didn’t know how to do it. It just made sense to adopt that attitude, that mode of dress, that set of tropes that separated the masculine fancy dress from feminine. But dressing up is a skill - not a thing we’re born knowing how to do well. Just like wearing different kinds of clothes or properly applying makeup.
It was a strange thing. Fashion and makeup were things I understood quickly; I had some training with from university in the context of theatre. I didn’t need to worry about it, but costume is different. Fashion is for everyone everyday. Costume is for specific people at specific moments, and I wasn’t sure how to express specific women at specific moments even if I knew how to be myself every day.
I skipped Halloween my first year. It ended up being in a half term so I was able to get away with not dressing up for work, which suited me fine. My first stint of actually dressing up was for Christmas, and that wasn’t presenting a different person so much as wearing a bunch of tinsel and putting baubles in my hair. I remember my stepfather saying it was a distinctly feminine selfie. Not that the others he saw to that point weren’t, but it really solidified my image for him.
"THAT COMMENT ENCAPSULATES MY FEELINGS OF NERVOUSNESS WITH DRESSING UP: IT EXPRESSED MY FEMININITY IN A WAY I NEVER HAD."
That comment encapsulates my feelings of nervousness with dressing up: it expressed my femininity in a way I never had. In a way that made it real, and it’s funny how we most express ourselves when we pretend. Dressing up created a level of exposure I wasn’t ready for that first Halloween. Tinsel in my hair I could do, but a whole outfit was too much; it made me too vulnerable. My outfit for world book day some months later was similarly modest: a dictionary. Pinned a bunch of printed dictionary pages to my dress and wandered around looking like a heap of paper. Conversation piece to be sure, but it was fun, and it felt more me.
A fancy dress party in spring was a turning point for me. A simple cat ear/black dress affair, but it broke the barrier, and suddenly I wasn’t so nervous. It’s amazing what a good experience at a party can do to make someone comfortable. I’d worked so hard to be me, I didn’t want to be someone else. The dressing up carried a different meaning - it wasn’t about escape anymore. It was about being myself in a fun way we don’t get to do very often.
The shift from escapism to the here and now was the thing I had to internalise. I didn’t want to dress up that first Halloween because I was enjoying being myself; I didn’t want to be anyone else, anywhere else. I wanted to be me in the now. Happy as I was - no portrayals, thanks. It was so momentous to step out and shed that mask of masculinity, even a different feminine mask was difficult to accept. I had to realise that dressing up, adopting a mask for fun, wasn’t a compromise. It was another way to be me.
This year, after some fancy dress parties and a little more time to build up courage, I finally am out for a wedding on Halloween and I have an outfit planned. I’m even looking forward to it! But it’s taken a year of dipping my toe in and discovering how I might pretend again. The part of transitioning people don’t tell you about is the internalisation of the change: that process of making expression automatic, second nature and normal. I was afraid of dressing up because I had to take the time to fully own my new image. Once I had done that, I was able to open up and pretend; I could show the world myself living fantasies again. But not to get away. Not as an escape. This time, it was to be me.