Women Dressing Men


Jason Fulford, from series in Vestoj ‘On Masculinities,’ 2016.

Clothes tell stories; this much we know. They also provide compelling material for the stories we like to tell ourselves: such as, ‘Men don’t like shopping for clothes’, or ‘When it comes to style, a woman knows best.’ The New Yorker writer Judith Thurman once compared her insatiable hunt for new clothes to men who fish, or who go to the woods with a rifle; ‘While they bag dinner, I bag a dinner dress.’ It’s a joke, of course, but when it comes to how men choose to express themselves through dress, the truth has always been that a not insignificant number of them will happily release that obligation to their partners and wives in favour of other pursuits.

It is a well-known fact that if you go shopping with a particular item in mind, you’ll never find what you were looking for. The pursuit of love, similarly, is more a game of luck than design; the partnerships we form in life begin in inauspicious circumstances, and expectations never fail to give way to different kinds of realities. When reflecting on the expression of masculinity through dress, the lens through which women see their boyfriends, husbands and lovers is a useful refraction then, and one which illuminates how vital one gender is in the making of the other.

To better understand the complexities surrounding how we see men, I met five women, aged between seventeen and eighty, and asked them to speak about their significant other’s clothing. How women in love view masculinity, and how might they ‘act it out’ via the clothing they choose for their partners, is without doubt an underexplored question. These five conversations, and relationships, form only a few small fragments in response; but like most fabrics, patterns emerge in the weave.


Elisa Benaggoune, seventeen years old from Maidstone, Kent and her boyfriend, eighteen-year-old George. Together for two years, they met ‘on Facebook through mutual friends, and then it just kicked off like that.’

Claire: What were your first impressions of George’s clothes?

Elisa: When I first met him he was wearing a purple jumper that was really silky and normal jeans, and he was wearing these shoes that had a sandy texture. I don’t know what to call them. They were like, fashionable slippers. I was like, ‘Damn, he’s really interesting.’ Oh – and we were colour-coordinated without even planning to.

Claire: And when does he look most attractive?

Elisa: On a special occasion. He’ll be wearing a blazer jacket, one without sleeves, with a smart shirt underneath and jeans. He always wears jeans. And those smart shoes that I can’t remember what they’re called, but they’re really leathery? Brogues. Best outfit ever. What I love about brogues and blazers on him is that it totally spins the whole outfit into something else. So when he experiments with smart and casual wear, I love it because it shows that he can take full power and control of how he wants to look. It just makes me fancy him even more.

Claire: How much thought do you put into a single item of clothing you purchase for George? What are the considerations?

Elisa: I think about his body shape, because it is quite different to lots of other people. He has wide shoulders and a thin waist. Because I know what it feels like when things don’t fit, I always choose things that will fit him properly. I find materials important, but I don’t look at labels because I tend to go more towards vintage. I think more about the quality. George and I don’t wear a lot of brands: he wears vintage too. Having your boyfriend wear that is, like, golden!

Claire: If George were to take upon himself some traditional markers of femininity like dresses and high-heeled shoes, describe what you think your reaction would be.

Elisa: I’d be so happy! If he wants to wear clothes like that and make it look manly, then I’ll love that. It’s so cool because it would look so different on him. I’ve always wanted to explain to people that you can wear women’s clothes and still look like a man, and we can still wear men’s clothes and look like a female – there’s no difference. It’s like David Bowie. And we share clothes all the time. He gives me his jumpers and shirts, and I just wear them out. And he wears my clothes. A week ago, he was wearing my joggers: he wore them at home and in town, and I was like, ‘Oh, George.’ (Laughs.)

Claire: So it is important to you that George looks ‘manly’ in some way?

Elisa: I think it’s definitely important for him because that’s a part of you that doesn’t really go away. It’s important for everyone, because as you grow with yourself and with your partner there’s always that reminder that tells you that you are a female or a male or… other. It’s always going to be important for everyone because being feminine or masculine is self-expression, and you have to remember not to lose that expression.


Stephanie McCabe, a fifty-five year-old plus-size clothing storeowner from Newbridge, co. Kildare, Ireland, on her husband Morgan, fifty-seven. They have been together for thirty years.

Claire: What were your first impressions of Morgan’s clothes when you first met him?

Stephanie: When I met him first he was wearing a grey pinstripe suit and a white short sleeve shirt, which I hated. Bear in mind this was thirty years ago. Even though it was kind of preppy really, and I like that look, there was a bit of tweaking to be done I felt – over time I got there. I wouldn’t have had much time for him, looking at him from a distance, because he was so conservative: I thought he wasn’t going to be fun. I just thought, ‘He’s not for me.’ I actually told my parents, ‘Oh God, I wouldn’t ​sit on him!’ That’s exactly what I said! Then about three weeks later I met him in a nightclub in Dublin, and he’d just finished work or something before he arrived in. And we started talking. And there was a whole different person behind that conservative look. And the rest is history really.

Claire: So his personality was different to the signals his clothing gave off?

Stephanie: Even growing up, he was conservative, but a little bit different. He wouldn’t be afraid to push the boat as regards clothes and style. Back in the mid-Seventies – before I met him – his mother was very involved in this charity organisation that she had to go over to Chicago once a year for. And she used to bring him home clothes. She brought him home like a ‘Saturday Night Fever’ white suit. It was actually kind of a cream suit, with huge big lapels on it. And he wore it to the local disco. The ultra violet lights were on at the disco, and he was wearing white underpants, and all you could see on the dance floor were the white underpants through the cream suit. (Laughs.)

Claire: What has changed most about his appearance since those days? What was your role in these changes?

Stephanie: He’s put on weight, but you know, not an awful lot. He won’t wear short sleeves anymore. Mainly he’s wearing finer clothes now, things that are a little bit better, more expensive. He’s on the local county council, and he works in the equine industry now, and he’s very involved in the Gerard Manley Hopkins Literary festival that’s on every year. So he has a different look for each event. He has a more flamboyant wardrobe for the artsy part of his life, if that makes sense. And for the equine part of his life, it’s very much a preppy, Ivy League look. I really love that look. We very much have the same taste. Every single morning for the thirty years that we’ve been together, without fail, every single morning, he stands beside ​me and the mirror, and says, ‘Do I look okay today Steph?’ Does this look okay with that?’ Every morning. He likes to look well.                                                                                                                                  Claire: Who wears the trousers?

Stephanie: One leg each, Claire – one leg each.


Justine Picardie, fifty-five, a writer and biographer from London who has written books about both Chanel and Dior, on Philip Astor, fifty-seven, aristocratic barrister and owner of Tillypronie Estate, Scotland.

Claire: What was your impression of Philip’s clothes when you first met him?

Justine: Although it sounds a bit odd, I don’t think I had any distinct impression about his clothes. You know, at the time I met Philip I had worked for Vogue and Harpers Bazaar and was deep in research for a biography of Coco Chanel, so hopefully I’m somebody who is alert to the signals that clothes give us, which is why it’s interesting that when I met him at a dinner party in London, I genuinely have no recollection of what he was wearing. But I think it’s something to do with the fact that I found him so… his conversation so engaging. When it comes to Philip and clothes, I would say my first strong recollection was when I first went to stay with him in Scotland.

Claire: What shifted in your perception when you saw him in his family home?

Justine: Tillypronie had belonged to his family, and he inherited it when his father died in his early twenties. But the house has got lots and lots of clothes in it, signs of the family past and present. Traditional Chameau boots, not fashionable Hunters, and tweed jackets – I think the first thing I noticed was the tweed. It’s called Tillypronie tweed, and it’s made by a local person in the village. When I saw that I thought, ‘Gosh, that’s so beautiful.’ I was brought up in London so I don’t know if I’d ever seen tweed like that; it’s the colour of the landscape, a very soft green with a heathery colour threaded through it. I do remember thinking that it was extraordinarily beautiful.

Claire: It’s interesting that clothing as a symbol of that lifestyle is important to Philip and yet separate from his everyday sense of style.

Justine: Exactly. I’ve never seen him in court, but the thing about being a barrister is that you don’t want to stand out in any way. But in Scotland, how he wears clothes is very different. I didn’t see what he wore until the shooting season started on August 12th – the glorious 12th. That’s when they go up in the hills and the men wear these old tweed plus fours and knee length hand matted traditional socks, tied at the knee with old, traditional ties. The way the people dress hasn’t changed for generations, and I remember thinking how there was a real sense of authenticity and integrity to the way Philip and other people up there were dressing. There are also other sartorial signals that anybody might pick up about Philip – Eton slippers, the old school tie: they’re little signals, just like people would pick up little signals about me, whether it’s a Chanel jacket, or a Dior bag.

Claire: Do you ever buy clothes for Philip?

Justine: I do. One of the things I became aware of very quickly when we first met, is that he is interested in my world though he is entirely himself. He’s very sure of who he is, so he doesn’t have to wear a fashion-y label to try and prove anything. He wears his own thing: he doesn’t have to prove anything. He will have a collection of Hermès ties, some of which probably belonged to his father, certainly no influence from me. Astor is an old family so Philip had a very traditional upbringing; he’s worn a lot of uniforms in his life. He went to prep school at seven, then Eton, then Christ Church in Oxford and then he joined the bar, you know, the chambers in the inner temple. He still wears his navy blue corduroy Eton slippers – they’re probably forty years old.


Margaret Walton, eighty years old from Hull, on her husband Harold, eighty-two, a former army officer. They just celebrated their diamond wedding anniversary.

Claire: How did you first meet your husband?

Margaret: We first met dancing at Racquets. We used to go every Monday night and we did the waltz and all things like that. That would have been the late 1950s; I was seventeen.

Claire: Can you remember what he was wearing?

Margaret: Crepe shoes – we didn’t have leather then. And a slim kind of suit and a thin, crochet tie. I’ve got a photograph of him – he’s got a light pair of grey trousers with a navy blue blazer. That was his best, best suit, you know. The ladies, the shorts was in – you know the hot pants – and then when we used to go dancing in town we’d wear the long dresses. Then the long dresses went out and other things came in. But the men didn’t really change.

Claire: Do you think your first impressions of him had much to do with the clothes, did you notice them?

Margaret: No, granddad didn’t have a thing like that. He didn’t have much money; he weren’t quite well off at all. He would have saved up to buy a suit. After we met he went in the Army you see, and then he lost a lot of weight. When he came home he’d only wear a suit and then he’d be back again in the Army. He’s never worn jeans in his life. He can’t stand jeans; he’s never had a pair. That’s something to say, isn’t it?

Claire: Do you buy him clothes?

Margaret: No, he likes to get them himself – we wouldn’t agree. I ironed three shirts for him before our anniversary party. One was purple. I said, ‘Wear the purple’ because our theme was purple, but he wanted the one with the flowers. I said, ‘No, put that one on,’ but he didn’t – he went for the other one. I said, ‘Ooh, that looks lovely with the grey suit,’ but he still went for the flower one! (Laughs.) I thought, ‘Would you believe it.’

Claire: When has he looked his best, in your memory?

Margaret: It was in summer. The late Fifties I think. I don’t think he was in the Army then… or he’d come home. We must have had our own little camera, and he was just stood with his back to this hedge. And he wore this blazer and the grey trousers and I really liked him in that – really nice. And of course he had a lot of hair then, black hair. He has looked well, I mean especially when he was younger; he was really smart.

Claire: What do you think your reaction would be if he were to suddenly dress in something more feminine – like putting a dress on?

Margaret: Oh, gosh. Terrible. Your granddad can’t stand ought like that. He hates anything like that – oh dear, no. Not for us, no. I hate to see that, anyhow. I never wear any of his clothes.

Claire: Do you think the men decide to be well-dressed or have the women encouraged what they look like?

Margaret: They’ve all lost their wives now, so I don’t know if the wives influenced them at all or what. But I often say to granddad, ‘Oh you’re not going in that are you?’ But he don’t take any notice. He’d do it all the more because I’d said something, you see. I think men make their own choices.


Lizzie Chappel, nineteen, a maternity nurse, on her boyfriend of two years, Josh, a twenty-one year-old building apprentice. She buys all his clothes.

Claire: When did you first meet one another and what were your first impressions of Josh’s appearance?

Lizzie: We’d be chatting on Facebook and then we went on a date. My first impressions of his clothing were pretty standard, nothing special. He was wearing straight leg jeans, which I hated, and a polo. It was a bit boring.

Claire: What has been your role in his changed appearance?

Lizzie: I’d say he was more fashionable now, and stays with the newest trends. I shop with him so I can pick and choose if I like what he picks. He doesn’t really buy a lot of clothes without me seeing it first. I buy clothes for him online, or in the town centre, in shops like River Island, Asos, Urban Outfitters, but he also shops a lot at Adidas.

Claire: When have you looked best as a pair? Why? What does that require?

Lizzie: At weddings we usually coordinate our colour scheme: one wedding I wore a pink dress, he worked a navy blue suit and a pink tie the same shade as my dress. But my favourite outfit of his is a crisp white short sleeve shirt from Next with a pair of nice jeans and tan coloured leather shoes. Because he doesn’t dress up smart often, I like it when he does. I do like him in a tracksuit and trainers as well.

Claire: Seeing as you buy most of his clothes, do you think he cares what he looks like? Or does he care more what you think?

Lizzie: He cares more what he looks like now than he once did. He often asks what top he should wear out or whether things match, like shoes with a top, or a top with a particular jacket. But sometimes he doesn’t really care what I think, especially with sportswear and things – he always wants the latest football jacket and I hate that sort of thing. He tries to fit in with the lads he is friends with, as well as the fashion now.

Claire: And if Josh was to take upon himself some traditionally feminine items of clothing, like dresses and high-heeled shoes, what would your reaction be?

Lizzie: Shocked! It would be totally unlike him; I’m not sure I’d be able to accept it.

Claire: Who wears the trousers?

Lizzie: I wear the trousers but he thinks he does.


Claire Marie Healy is a writer and editor from London. She’s working on her first book. These interviews were previously published in Vestoj ‘On Masculinities’ (2016).