Hobbies to pick up if you are bored 🏳️⚧️
Note: This piece was written keeping in mind men who might enjoy wearing womens’ clothes because that’s my experience, but I hope you can get some inspiration out of this if you don’t fit those assumptions.
“Cross dressing” as a term has some connotations and associations and stigma and contentions. But “being gender non-conforming” implies a way of being, rather than an act to be partaken in. And “being transgender” is a personal and social reckoning you might have with your place in gendered society, which is pretty serious, more serious than wearing different clothes. (I hope you can have the strength to face that if you need to - there is still time.) It’s not my favourite way of putting it, but of all the ways of addressing this hobby “cross dressing” is the chillest one. And I really believe it can be chill.
For example, if you’re bored of dressing like a rectangle, then why continue? Yes sure, a slim-fitting suit might squeeze your sides if you have the right body type for it. But a skirt, or the skirt of a dress, can accentuate the organic shape of your body. A belted dress can achieve this too, when its elasticity makes it fan out away from the belt’s pinch.
If you’re bored of all your clothes having the same proportions, why limit yourself to them? A flannel over your t-shirt might add a fun layer, but if it’s warm you could use a cropped cardigan that only adds to your top half. Or if it’s cool, you could use a shirt dress as a light overcoat. A skirt or curvier jeans might sit at your waist rather than closer to your hips. A mini dress might end higher than your shortest shorts do while looking half as scandalous.
If you’re bored of your clothes having the same three or four textures, why not try something new? You could try a ribbed sweater, or an embroidered dress, or a flounced blouse, or a pleated skirt. You could wear soft leggings instead of your usual rough jeans or fibrous khakis. You could wear a mesh cardigan instead of your solid flannel or a feather-light blouse instead of your structurally invincible button-up.
If you’re bored of how your clothes fit - well, fit is the most important aspect of your wardrobe fundamentals, so it may seem like you can’t compromise on this. But M and F clothes can both fit well while fitting differently. I wear mostly men’s medium and large, yet strangely enough women’s medium and small. I look good in comfortable straight cut blue jeans that give me a relaxed cool, with a light fitting band tee that makes me pop without making me stick. But I also look pretty good in a dress that hugs my body, which my curves can show through and whose skirt can flow off of my hips.
There are more aspects in which the “opposite” gender’s clothes can offer greater variety, but discovering these aspects is an exercise left to the reader - earnestly. Part of the fun is the experimentation and novelty. It can be delightful to look at yourself in the mirror and see something you’ve never seen before, or to finally see something clearly that you’ve only briefly glimpsed before. It can even be euphoric.
As an aside: Cross dressing is celebrated as a purely fun activity too - drag exists! I’m not very knowledgeable about traditional drag. I don’t watch RuPaul and I’ve only been to one show (which was fantastic, I highly recommend). I’m sure you can read about it somewhere else. I will say though that there are more forms of drag than the kind you do at clubs. Femboys have been a meme for a long time (particularly among terminally online weirdos e.g. on 4chan). Wearing a mini skirt, thigh highs, an oversized hoodie, a whiskers face mask, and cat ears wasn’t just a fashion sense, nor was it porn. At its height in the mainstream, being a femboy was a celebration of a new way to embrace femininity in spite of gendered body characteristics that don’t fit female beauty standards. Looking up femboys in 2024 often delivers you to pornography, and the zeitgeist opinion on them has turned to “🤢” due to that porn (and other reasons that aren’t worth ink). But the spirit of drag is still thriving in the Polish femboy subreddit.
But it also doesn’t have to be euphoric (or performative), it could just be fashionable. There might be a million ways you could look good that you haven’t even considered before. Look at Young Thug - he needed something flamboyant, fresh, and joyful for the cover of his flamboyant, fresh, and joyful mixtape No, My Name is Jeffery, so he donned Alessandro Trincone’s beautiful periwinkle tiered dress and queened out. You CANNOT tell me that he doesn’t look good as hell here, or that he didn’t come up with a perfect album cover. Or look at A$AP Rocky, who had thousands of fans dressing like Slavic grandmothers, and having fun doing it. I don’t bring up this viewpoint to say that gender non-conformity should be decoupled from queer culture, that’s absurd. I only mean to be encouraging to those who don’t think their gender is complicated. I felt very strongly that I was a cis man when I started wearing dresses. (I feel differently now, but I guess I am different now.) I wasn’t hoping to change my gendered characteristics, I was only hoping to look good, and willing to be brave in that pursuit.
Transphobia is why it’s so difficult to be a part-time gender “nonconformist”. You will encounter transphobia without being transgender. For men, cross dressing has been thought of as an emasculating act. A man who is wearing women’s clothes must be trying to either humiliate himself or experience a homosexual flavour of voyeurism. Lately, a massive political effort is being put into conflating transfemininity, and even drag, with pornography. Another old trope is conflating it with deception. Meanwhile, the classical flavour of misogyny rears its head on the other end. A woman wearing clothes that are clearly for men must be making a political statement, showing her strength in spite of her femininity. This is unjustifiable, throwing away our precious fetish of femininity is verboten. Of course this stuff is inescapable, but on a personal level I still think it’s bullshit. Say any of that shit to my face, I dare you. It’s just clothes. Young Thug wore the dress because it was cool. His own mythology says he wore it to conceal a rifle. I don’t wear Uniqlo dresses because I’m gay and I want sexual stimulation through sissy exhibitionism; I wear them because I look good in them.
Of course that stigma and transphobia requires material change and heavy activism to be crushed, not just individual acts of resistance. I won’t lie to you and say that flagrantly rude stares are the worst part of dressing “wrong”, or that you can do anything immediate against even the stares. But I think if you’re around the right people it can definitely be worth it: You might look different in the public eye but you’ll look almost the same to your real friends - just in a new style. You might look different to yourself, but hey, is that so bad?
