I wore men’s clothes for a month – and it changed my life

It’s 9am and I’m having breakfast at the House of Commons. I’m wearing a three-piece pinstriped suit, matching tie and pocket square, and the confidence of a mediocre white man. To my left, a man is pouring me coffee; to my right, another is listening respectfully. How did I get here?

Last year, I saw a few posts about an ‘Octieber’ challenge (wearing ties for a month) and immediately thought it would make an interesting experiment. I’m working in a big city right now and spend an average of four to five hours per day commuting. I’m quite public-facing, I speak at conferences and I generally travel on public transport. What might happen if I wore a tie every day?

Somehow, my first ideas involve making the tie ensemble more feminine. I had visions of swing dresses and loose, sexy, floppy ties, with the tie simply another accessory to my powerful femininity, like a bold new lipstick. But, shopping with my daughter, I have my Primarkian Damascus moment: Why is clothing gendered at all?

Why on earth have I spent the last 32 years plodding obediently into the ‘Womens’ Clothing’ section?

I look at my precious daughter. All her life, I have enjoyed cultivating in her a tiny subversive streak called feminism. It’s partly protection – otherwise she’ll be another ignorant victim of sexism – and partly straight-up rejection of society’s imposed values. I was delighted to overhear my other daughter (aged 11) explaining feminism succinctly to her friend: “It’s basically the idea that no-one can tell you what to do just because you’re a girl. Or a boy.” I’m sure my children are a veritable nightmare at school (they tend to yell ‘sexism’ alarmingly wherever they find it), but it’s been a privilege and a pleasure to teach them about feminism. We have analysed, deconstructed and sometimes raged against the patriarchy together.

So why on earth have I spent the last 32 years plodding obediently into the ‘Womens’ Clothing’ section?

I realise that this challenge should mean totally embracing everything about menswear – tasting all of the forbidden apparent penis-fruits that I appear to have denied myself for so long, willingly, like an atheist yet abstinent Eve. I want to look sharp. I want to be dapper. I want to wear pocket watches and cravats and waistcoats and starched collars and brogues. I don’t want to add a tie to what I already have, I want to know if it is possible to look formal and be comfortable at the same time.

If I were to draw a graph showing ‘how formal I look’ and ‘how comfortable I feel’ for the preceding twenty years, it would be what we mathematicians call a negative correlation – as one increases, the other decreases proportionately.

Looking formal, for a woman, generally involves showing more flesh, wearing tighter and more figure-hugging clothing, higher shoes, tights, Spanx, jewellery and complicated hairdos. It’s a list of things that make me feel physically uncomfortable and self-conscious. Any time I have left the house to do anything vaguely important, I’ve been uncomfortable, and the more important the thing, the more uncomfortable I’ve been.

We need to talk about pockets

This fundamental truth floors me. This is patriarchy in action. Not only have I been complicit in the societal conspiracy to judge me primarily on my looks, I’ve had to operate within a system that makes me less confident, more self-conscious, and generally in more physical distress than your average man.

My boyfriend appears from the loft with a three-piece subtle black pinstripe from French Connection he has grown out of. I try it on and it’s magic. It’s one of the best gifts I’ve ever been given, and on no particular occasion. Happy Birth-of-A-New-Freedom-Day to me. This suit does not make me uncomfortable or pained in any way.

It looks smart and stylish but does not dig in, does not cling, pinch or make me frown at my reflection where it could be a little looser, a little longer and a little higher. It just is. It is at this point that I start to fully realise how crowded my head is on a typical work day: how full I am of nagging doubts about what I’m wearing and how I look to others. I realise that I have been constantly looking at myself all day in mirrors and shop fronts and car windows and focusing on that bit and breathing in and sighing and feeling inadequate. Because womenswear is designed to accentuate your shape, and if your shape ISN’T ‘tiny-waisted-large-but-pert-breasted-and-no-stomach-fat’ then it always – but always – looks a little ‘wrong’.

Day one: We need to talk about pockets. The clothes I’m wearing now have bountiful, multifaceted, capacious pockets. I have nine of them today. I counted ’em. On a typical day of wearing womenswear, I have NONE. Another realisation like a wet herring to the face: the ‘handbag vs pockets’ thing is huge confidence-underminer, another terribly effective, if inadvertent way, to hold women down. I remember being crouched over my handbag, furiously ferreting for a business card while my male colleague coolly produced one from his manly chest-cavity as though he lactated them to order.

I remember having to smile and flirt queasily with a security guard to get through the station turnstiles because I had tucked my train ticket into my bag and it had swooped out unseen onto a toilet floor somewhere. I remember the guy who verbally harassed me on the street for fifteen minutes because I took my phone out of my bra and that meant I touched myself in public and was therefore ‘asking for it’. Having pockets (and pockets that are actually fit for purpose) is undeniably a feminist issue.

The men I’m mixing with will happily mix navy blue suits with black shoes, pink shirts with red ties and trousers with jackets three shades different, and appear to care not a jot

Today, I am experiencing the joy of symmetry. I walk without hunching lopsidedly over a bag. I can confidently locate my money, keys and purse because they all have allocated, easily-reachable compartments about my person. It is hard not to smile about this and everyone notices.

Day two: I feel it’s not really in the patriarchy-smashing spirit of this challenge to continue to ask my boyfriend to do my ties up the night before and leave them on the bedpost. I take to YouTube and it’s like entering Narnia though the unnoticed door at the back of Tie Rack. Call me ignorant, but I’d always just sort of assumed there was one (maybe two at a push) type of tie knot – ‘vaguely triangular-looking.’ But it’s all trinity Knots and Full Windsors and Half Windsors and Van Wijks and Tulips and the stunning cascade of the perfectly zigzagging Eldredge. I’m excited. I feel like this is a way to add flair and depth to my outfits without spending too much time or effort on them. A few hours of practice later, the Yonic Tie is born. I’ve managed to tie a tie that looks a great deal like a clitoris and I couldn’t be happier about it – the irony! I start hashtagging merrily.

Day four: I’ve been noticing the attire of men around me on the daily commute and I’m struck by the fact that no-one seems to particularly care about coordinating items. There are entire articles in magazines on the hot topic of What-Goes-With-What in womenswear. It’s one of the most frustrating things about dressing oneself – you find the right suit or the right dress, but then need to find the blouse, the jacket, the shoes, the belt, the coat, the hat and the gloves that all ‘go’ appropriately. Sometimes you have to start again from scratch. Sometimes you end up crying under the duvet.

I’m sure this stuff is pretty important at the high-fashion end of menswear too. But the men I’m mixing with daily (not just provincial men, but movers and shakers, CEOs and investment wankers) will happily mix navy blue suits with black shoes, pink shirts with red ties and trousers with jackets three shades different, and appear to care not a jot. I’m gleeful at the thought of such freedom. I wear the same pair of shoes for a week. I wear a waistcoat and trousers that aren’t quite the same colour. It’s so refreshing I could cry. The simple mathematics of permutations means I’m no longer stuck in an exponentially-increasing spiral of possible outfit-choices, but helpfully limited to the much smaller factorials of three suits, five shirts and a handful of ties (told you I was a mathematician). It saves time for much more fun things like eating and sleeping.

One thing that does strike me when shopping is the lack of norm-referencing between tops and bottoms

Day seven: I’ve now worked out, through trial and error, that I am a 38″ chest and a 34″ waist in menswear. It feels like so much less of a judgement than ‘14’, or ‘16’, but I’m aware that’s because it’s new to me and therefore doesn’t have the concomitant baggage. Now, I’m sure men have to deal with very similar “I’m X size but I wish it was different” issues to women, but one thing that does strike me when shopping is the lack of norm-referencing between tops and bottoms.

As a woman, clothing manufacturers will insist on trying to cram my top and bottom into the same label (when patently this is not the case for a majority of women). I can buy separates, of course, but there’s an implicit ‘abnormal’ judgement there and dresses are chaos. Men also seem to have options for collar size and chest that are more flexible overall. Is this because men’s bodies are more diverse than women’s? The evidence of my eyes seems to offer every possibility that this is poppycock.

Day nine: shoes. It’s occurred to me that it’s not fair to embrace menswear without trying the footwear, too. I’m a size six, which is within the accepted ‘normal’ range of both mens’ and womens’ shoe sizes, so I buy a pair of canvas lace-ups from my usual shop of choice, which mimic my customary style at work, but are from the men’s section. I had naively expected very little difference, but I was so wrong. These shoes are wider, thicker on the soles and, without a doubt, more comfortable, despite exactly same price. Will the injustice never end?

Day 10: Someone I chat to about this challenge pointedly notices that I have gone to some effort to ‘feminise’ my outfit by keeping my hair loose and adding an intense shade of lipstick. Something that is keeping me going this month is other people telling me that I look attractive. I can’t deny that looking groomed and beautiful is still an important factor in how successful I am professionally and personally. But to me this is about making a point that I can wear this stuff without looking dowdy or unkempt or ‘blending in’.

I’m starting to feel like it’s ok to be big, broad and solid. This is the antithesis of literally every message women get about their bodies every single day

It’s an uncomfortable truth that the privilege of being white, average sized and reasonably attractive allows me to ‘get away with it’, and talking to other women about this soon reveals that anyone alternative–looking or what society might deem as ‘fulfilling the lesbian stereotype’ tends to get a much more negative reaction than I have. A male friend asks if I’m getting my suits tailored, as they fit so well, and I answer “No, it’s just because I’m built so good and manly!” I’m starting to feel like it’s ok – an advantage even – to be big, broad and solid. This is the antithesis of literally every message women get about their bodies every single day. I’m reeling because suddenly it’s ok to take up my own space.

Day 13: Today is The Big One. Today, I am taking my menswear experience to the next level. So far, when people ask, I’ve been saying, “Everything is menswear, apart from the bra!” Today I’ve decided to ditch it (gulp). Make no mistake, I’ve never done this before. I’m not one of your ‘skipping braless through the meadow’ types – and I have some considerable 38D jugs, too, so this is not a decision I have taken lightly. I’m doing it because it scares me so much. How can it be such a big deal? Why do I care so much? I realise one of my greatest body hang-ups is the idea of massive, droopy udder-boobs and lack of waist, and that wearing a waistcoat and shirt will probably give me enough support that no-one will notice except me.

I’m pretty sure no-one notices except me.

I post triumphantly on Facebook: “I’m the No-Bra Cobra!” I’m not sure I’d want to do it every day, but I’ve successfully confronted some of my greatest clothing issues and feel better for it.

Day 15: I’m going to a wedding today. Months ago (because I’m organised), I’d picked out a dress, shoes and accessories. This challenge was for work, so I’m not worried about ‘going back’ to womenswear in my own time – except I can’t. I try on the dress. It’s lacy and forest green and flattering, but it feels wrong. I’m cold and my arms are exposed. I try on a tuxedo and bow tie instead. “Is this ok?” I ask my boyfriend. He thinks I look awesome, but still mischievously introduces me as ‘the magician’ at the reception. ‘Day into night’ is exceptionally easy – I take off the bow tie and jacket, loosen a few buttons to get down on the dancefloor. Dancing is also appreciably more fun when the danger of overexposure while spinning is removed.

A man leaning on a wall addresses me: “You looking for something, baby?”

Day 16: I’m shaken. Today was my first truly negative experience (the bald guy leaning out of his vehicle to shout the self-evident “You’re wearing a TIE!” doesn’t count). I’m walking by the riverbank in the City and while following directions I’ve taken a wrong turn into a park. I turn around, seeing a no-through road, and a man leaning on a wall addresses me: “You looking for something, baby?” Something about his sleazy stare adds extra menace to the endearment, so much so that I am emboldened to say, simply, “I’m not your baby.”

And that’s the end of it, right? We’re all reasonable people and I’m lost. This is not the way to help and you’re surely not interested in pursuing some sort of sexual advance at the very obvious risk of making me feel unsafe in this dark park.

Except, of course, he was. Four words, nothing obviously offensive or harassing, but enough to make the hairs on the back of my neck stand up and, combined with the move towards me, enough to make me chilled with prickly fear: “Of course you are.”

I have no way of knowing if this behaviour was exacerbated by what I was wearing, whether he was encouraged by the confidence of my bearing or whether anything else about my clothing had an effect on this encounter. I do know I am wrong to feel even more indignant that I hadn’t led him on because of what I was wearing, and that thought needs confronting, dissecting and developing. But not now. Now, I just need to run away from a dangerous situation that a suit and tie can’t save me from.

Day 20: I’ve been posting all over social media and I’ve had so much positivity pouring in from other women that I’m grinning from ear to ear. After a difficult meeting, all I need is to see positive comments and I’m back to unstoppable in minutes. I’m lucky enough to be part of a large feminist community on Facebook (allied with the exceptional ‘Guilty Feminist’ podcast) and they’re giving me just the combination of support and challenge I need. I’m not sure I could do it without them.

I’m striding through the Houses of Parliament with an umbrella like I’m king of the world

Day 21: I’m trying hard to find a clothing company that makes unisex suits. The UK seems to have nothing. A friend suggests Kipper Clothiers in the US, and I’m delighted to see that they are incredibly forward-looking. I was beginning to think the whole clothing industry was indelibly invested in heavily gendering clothing. I contact them, and they offer on the spot to send me some samples.

Day 22: I’m striding through the Houses of Parliament with an umbrella like I’m king of the world. Could it be the suit and tie? Have other peoples’ perceptions changed, or have I?

Day 27: It’s nearly the end of the month and I want to try something new. Keeping the tie, I go for vintage, Bletchley Park-style glamour. I’m wearing a khaki pencil skirt and muted herringbone tie and victory rolls. It’s the first time in a while I’ve worn womenswear. Within an hour, despite the brown sensible shoes I’ve chosen, the back of my heel has bled through my tights, my bra underwiring has escaped and is now pointedly stabbing my flesh, and I’ve got severe pins and needles from trying to keep my legs together for an hour and a half on the train. I feel awkward and frustrated without pockets. Maybe there’s no route back.

Day 30: I’ve been blown away by the difference I’ve felt. Maybe some of it is the novelty value; my ‘rational brain’ tells me this is bound to be the case. But I can also say for sure that I’ve never worn clothes that have made me feel so comfortable, made it so easy to regulate my temperature and have been so simply flattering – never. Just putting on womens’ tailored trousers today – which at first glance may seem extraordinary similar to mens’ – makes me notice how tight and unforgiving the cut is, how clingy around the bottom and stomach they are and how there are no pockets. Have I mentioned pockets yet?

I can’t pretend I have any interest in feeling unnecessarily uncomfortable and self-conscious ever again. I started with #Octieber in 2016 but I see the need for another #NoGenderNovember in 2017. I won’t stop until I spread the message. We have choices, men and women. Gendering clothes is ridiculous, unnecessary and totally damaging. I refuse to be complicit in it.

Image descriptions and credits

1. Two suit-wearing mannequin torsos at the Why Not Boutique at 1348 U Street, NW, Washington D.C. on 1 April 2011. The left (background) model wears a pink shirt, light green patterned tie and a black jacket with just the middle button done up. The right (foreground) model wears a small-checked blue/white shirt, light pink/blue paisley tie and a grey jacket with very fine medium-wide white check and a grey/light blue paisley handkerchief in the pocket on the viewer’s right. By Elvert Barnes Photography, shared under a Creative Commons License.

2. White mannequin in jeans and a dark grey ‘digital paraphernalia’ hoodie with detachable sleevelets and a large front zipper pocket, described in entry on Flickr as “for your iPad”. By Sen Chang, shared under a Creative Commons License.

3. Lucy Rycroft-Smith, who is of Caucasian appearance and has shoulder length hair, stands in front of a white door. She looking to her right, with her hands in the pockets of the trousers of her smart and comfortable-looking navy suit. She also wears a dark purple scarf and tie that complement her lipstick. Picture supplied by author.