What I Learned From Wearing "Menswear" For A Week

by Lani Irving

Type "menswear" into Pinterest and the results aren't even half as interesting as those that arise if you type in "womenswear." It seems, at least to my untrained (in the field of menswear) eye, that choosing clothes aimed at women offers up a whole load of options that "menswear" simply doesn't (despite the rise of androgynous fashion). There are so many more shapes, more colors, textures and prints to choose from in the realm of "womenswear," that when I first decided to take on the challenge of wearing only "menswear" for a week, I was actually a little perplexed about what my options would be.

With my short hair, lack of makeup and no recollection of wearing a pair of high heels in the last five years, I don't tend to consider myself typically "girly," but when I started to look at "menswear" in its most prescriptive sense, I realized how wrong I was. I hadn't noticed before this point what a struggle it is for me to get through a week without wearing a pair of patterned leggings or how much I use my clothes to work with my curves.

I think it's important for me to note that this whole experiment is framed within the experiences of a cis woman. I was born female, I identify as female, and physically embody many traits conducive to this. Whatever I wear, most people would cast a glance at me and identify me as a woman. Nobody judges me for wearing "womenswear" and most "menswear" items overlap with those we see in "womenswear" anyway, so nobody judges me for wearing those either.

My gender identity is readily accepted by the people around me and nobody is scrutinizing it, so wearing clothes aimed at a different gender is easy for me. Sadly, this is not true for everyone and there is often seen to be a pressure on trans people to "pass." I cannot in any way speak for the experiences of trans people so I would like to encourage readers to take a look at this article by Jetta Rae, which discusses dressing and "passing" from a trans perspective. I would also recommend listening to (and/or reading the lyrics to) Against Me!’s Transgender Dysphoria Blues, which explores singer and guitarist Laura Jane Grace’s experiences as a trans woman. Not only is it a great album, it is also a really accessible way to begin to consider some of these contextual issues we can't ignore when it comes to discussing gendered clothing.

With these points in mind, let's take a light-hearted look at how I got on when I spent a week wearing only "menswear."

Day One

I have a pair of grey Topman jeans that I, ahem, borrowed from my boyfriend many moons ago. I threw these on but realized that I would actually have to fix the hole near the zipper this time to avoid flashing my undies instead of just wearing a long t-shirt or a dress to cover it up, as I have on previous occasions. I teamed them with a borrowed checked shirt, with one of my own t-shirts underneath and a pair of gender neutral Dunlop sneakers. Day one was really no big deal. I went out into town, I saw my friends and colleagues, and nobody said anything. Technically speaking, my outfit was all "menswear," but it just wasn’t remarkable to see these clothes on a woman.

I wonder why women’s fashion has appropriated items that were initially seen as menswear, but the reverse cannot be said to be true in mainstream fashion. Women wear trousers now, which was at one time unthinkable, but where was the men’s skirt revolution? I keep thinking about Eddie Izzard, about the interview where a reporter asks him about wearing “women’s dresses,” to which Izzard quips, “they’re not women’s dresses, they’re my dresses,” and how we don't say that women are wearing "men's trousers." I want to delve deeper into this issue and find out if it goes beyond practicality and into patriarchy, but I think that is a whole other article in itself.

Day Two

I wore the same jeans again, with grey Converse low tops, a green Vans t-shirt and a plain grey hoodie. I felt so incredibly dull. These are all items I wear separately, but I normally dress them up in other ways, like with a playful patterned skirt or cardigan. Sticking to this rigid idea of "menswear" is so boring! The most excitement that could be gleaned from this day is the constant suspense of wondering when and how far my jeans are going to ride down next time I crouch or bend over because, tried as I have, I have never managed to find jeans that actually fit me properly, including those stolen from my boyfriend. Luckily, I have anticipated this risk and worn large underwear.

Is menswear really limited? Perhaps I just don’t know enough about it. I decide I need to pay more attention to what’s out there in terms of menswear.

I am missing dressing in a way that is comfortable for my shape. I have a belly, I have a muffin top, and usually I would choose items that skim over this area, for comfort and for confidence. There is no hiding in menswear. My belly sticks out over the tight waistband of the jeans and the t-shirt clings to it. I notice my belly’s reflection in a shop window as I pass and I actually find it kind of cute.

Well, that was unexpected.

Still, nobody has said anything. Maybe I need to up my game? Or maybe it just suits me. I start trying to picture my other female friends in this outfit and some of them would surprise me, others not so much, but not for reasons of gender — just for reasons of personal style.

Day Three

I have to confess that I woke up incredibly late for meeting someone and threw on the same outfit from yesterday. My only development today is that I realize that I have not been layering as much as I usually would and that I am feeling the cold a little more.

Day Four

I wore a blue, black and white checked shirt (from the charity shop), over an Iced Gems print t-shirt (by Paint The Stars clothing, a hand-me-down from my brother), with black jeans and Converse sneakers again. I am getting really bored of jeans. I don’t really tend to wear jeans usually, especially since I discovered the magical comfort of jeggings. I looked in the charity shop for men's trousers I could potentially wear but was a little baffled by sizing and found that nothing looked comfortable or appealing. I decide I must raid my boyfriend’s wardrobe in search of some more interesting trousers at the weekend. I suppose today at least I managed to bring a fun print into the outfit, but I am still not getting excited.

Still I have received no comments or interesting reactions other than a friend asking, “Have you lost weight?” to which I replied, “I don’t think so, but I am wearing baggier clothes than usual!”

Day Five

Look at my face. Look how fed up I am. I teamed another checked shirt with a fairly inane purple sweater and — you guessed it — jeans and sneakers. I am starting to understand why my partner's wardrobe contains about 200 checked shirts and I must try to never make fun of him for this again. I think maybe if I had more experience of menswear I could be more creative with this, but one thing that keeps coming to mind is wondering whether things are "too girly" to be considered "menswear" or gender neutral, like my Dr. Martens, which are technically from their "ladies" range but are pretty gender neutral if you ask me. Still, I decide to stick to the rules set by the brand.

I start actively paying attention to what men, especially those in my age group, seem to be wearing out and about. Now, this may have been more interesting if I lived in, say, Tokyo, but I don’t — I live in the Northeast of England. I’m not saying there aren’t some stylish men up here, but their style seems to consist of different combinations of the same few items:

  • Jeans — mostly slim fit or skinny.
  • T-shirts — plain, or printed if you're feeling ambitious.
  • Formal trousers — usually black, grey or navy.
  • Formal shirts — tie optional.
  • Checked shirts — can be dressed up or down, available in a wide range of colors but somehow still all look vaguely the same.
  • Long shorts — I saw a father and son duo wearing smart knee-length shorts with deck shoes. It wasn’t even that warm, but I think they were on holiday and trying to make the most of it.
  • Popular footwear choices — sneakers of various kinds, Vans slip ons, Dr. Martens boots, brogues and other formal-looking shoes.

I observed two notably eye-catching individuals, one of whom was wearing a Hawaiian-style print t-shirt with a grey cardigan, grey track pants and a diamond earring; and the other of whom caught my eye for being impeccably smart in a crisp grey suit with black shirt and tie, with his hair combed back into an immaculate quiff, wearing aviator sunglasses… indoors.

Day Six

I spend the night at my partner’s house, hoping to acquire some more interesting attire, but end up in another pair of his black jeans and a t-shirt for the metal band my two brothers used to be in. I realize I'm really not used to wearing jeans and a t-shirt without some other belly-disguising layer and do feel a little bit bare. I tuck the t-shirt in to try and make sure my midriff doesn't work its way out into the open and give me a chill.

I truly realize that I am not built for jeans, I am built for stretch. I want to be comfortable!

I also take a good long look at my handbag, which I have substituted for a screen printed canvas shoulder bag for this experiment. I wonder why I feel the need to carry so much stuff, what even is all of this?! I vow to go bagless tomorrow. I will make sure I have pockets.

Day Seven

I like this Ben Sherman checked shirt, even if my partner, after carefully mulling it over, suggests that it "does look a bit... This Is England." I team it with a skinny black tie, a pair of formal trousers (which I switched for jeans later in the afternoon) and a pair of not-so-subtle green and white checkered Vans slip ons. I think this might be some kind of smart casual. No, actually, I think I am Billie Joe Armstrong…. Yes, I am Billie Joe Armstrong. This is why I am not built for the 9 to 5 world — I try to dress "smart casual" and I end up as Billie Joe Armstrong. I can live with that, I grew up idolizing Green Day throughout my teens, I think I can make this work.

Day Seven saw me heading to a bra fitting appointment (as I did not ditch the bra for "menswear" week, except for a couple of post-work outings to the supermarket), which felt a bit of a strange thing to be doing in "menswear." Bra fittings can be a strange environment anyway as, even when you’re with a competent and respectful professional, you are essentially still getting your baps out for somebody you don’t know. I actually felt more self-conscious with my shirt on than with it off in the context of that fitting room. I think it’s easier to feel less self-conscious in a big open space with lots of other people around, whereas this was an activity that required me to be the sole focus of a stranger’s attention.

However, to and from the appointment I felt... great. Like power dressing. This outfit attracted the most attention, but it wasn’t all bad. I did have some odd looks and giggles, but they were all from teenagers. The part I really enjoyed about this was some, what I can only describe as, interested looks from other androgynously dressed individuals, the most notable being a young man in jeggings (and a checked shirt, how original!) with a Tegan Quin haircut who just looked at me for quite a while in the street. Not in a judgmental way, not in a way that made me feel uncomfortable, just in a way that made me feel like I was properly being seen.


I think this was the most important thing I took away from this week: The way our clothes can identify us as part of a subculture; part of an urban tribe. The way we dress is a way of branding ourselves and, as much as we say we shouldn’t judge people by appearances, the way we choose to present ourselves can act as an indicator of the things we are interested in, and possibly the type of person we are, regardless of gender. That, and a newfound gratitude for my collection of leggings.

Images: Author's Own; Giphy