The Tricky Politics Of Trying To Dress Your Boyfriend

When is it ok to turn all Trinny-and-Susannah on your bae?

The Tricky Politics Of Trying To Dress Your Boyfriend

by Lauren Bravo |
Published on

My boyfriend and I like to think of ourselves as a modern, enlightened kind of couple.

We both know where we stand on finance (I earn more, he spends less), on cooking (we both do it, he with more cheese), on cleaning (neither of us do it until once every two months when I empty a bottle of bleach in the bath and he blocks the hoover), even on how we’d split childcare and support our imaginary future children (I will continue writing, while he videos them falling over for You’ve Been Framed).

But there’s one question that nags away increasingly in my mind, and it is this: when is it OK to tell him what to wear?

I know, I know – it’s a doozy of a double standard. If he tried to exercise any kind of control in my wardrobe, I’d be slamming the door quicker than you can say, ‘You WORK those cropped flares and moccasins, girl’. In fact, making the kind of outré style choices that leave boyfriends furrow-browed is a modern badge of honour. Leandra Medine’s site Man Repeller was built on the idea, celebrating ‘she who outfits herself in a sartorially offensive mode that may result in repelling members of the opposite sex.’

And as someone whose most recent purchase was a pair of ‘Dickensian chimney sweep’ trousers, I feel I ought to have a liberal, free-to-be-you-and-me stance on my beloved’s wardrobe. After all, he’s endlessly supportive of my fashion efforts – and even when I can tell he’s lying (when he smiles with glassy eyes and says ‘Mmm, that’s very… cool’), I delight in wearing the thing anyway. But the unbalanced truth is that while he cuts me generous slack where my slacks are concerned, I have many opinions on his.

Most of my opinions are, ‘You just need more clothes’. I like everything he wears, I really do, but there are so many OTHER things out there I want to see him in. A wool pea coat, for one. Maybe a fisherman’s sweater. A shirt in any print other than check. Cashmere. Corduroy. I want to dress him up in my love, but also in Cos and John Smedley. It’s an uphill struggle, partly because he has such rigid ideas about what he can and can’t pull off, and partly because over every sartorial adventure of the past five years has hung the spectre of The Boots.

The Boots happened on one of our earliest dates – number five or six, maybe – in Topman. (I don’t remember why we were in Topman. Probably Claridges was full). In what I later learned was a fit of uncharacteristic financial abandon, this man who enters his weekly Weetabix budget into a spreadsheet, decided to buy a pair of Hudson ankle boots that he thought were £65. When we got to the till, it turned out he’d read the wrong label and the boots were actually £125. Screaming inside, he tried to look nonchalant and handed over his debit card anyway.

‘Cool!’ I thought. ‘A new dandy boyfriend who casually drops a hundred quid on shoes!’

But The Boots were never worn. I don’t know if it was the financial trauma or the fact they made him look a bit like Dick Turpin, but they just sat in the back of the cupboard, dusty and guilt-inducing; the ghost at the feast. After that, we became the Jack Spratt and his wife of dressing. He gets by on the leanest rations – a uniform of two pairs of jeans, one charity shop jumper, a couple of shirts, one pair of shoes that let the rain in – while I gorge myself on the fat of the fashion land, sweeping through my wardrobe every morning like it’s a hotel breakfast buffet.

He struggles with the elusive ‘smart casual’ – it’s holey jeans or a work suit, nothing in between – while smart casual happens to be the only area I’ve ever really conquered. Being slightly overdressed for the pub is kind of my thing, as is turning up to weddings and fancy parties looking like someone’s eccentric aunt who lives on a barge. And so, I help. I suggest things. I sometimes, VERY GENTLY and nicely, veto things. When your significant other is fashion-shy and you’re not, is it really so bad to take their hand and steer them through the sartorial wasteland?

When I float the question with a couple friends I’m actually surprised how wide the responses range – from ‘I’d never DARE comment on his clothes,’ to ‘I literally won’t let him go shopping without me.’ And while I worry I’m demoralising Matt every time I hold up a motif sweatshirt or a jazzy satchel, it turns out loads of couples I know are comfy with the complete opposite arrangement.

‘I wouldn’t dream of telling my husband what to wear – or I could, but I know he’d never listen,’ says Amy, 25. ‘But he will tell me if he likes my clothes, often because I need reassurance and he’s more stylish than me. If he really hates something, I usually don’t wear it around him. Not because I feel I can’t, I just really respect his taste.’

And it’s not like the balance of wardrobe power is only a deal for straight couples. ‘We do critique each other,’ says Katie, who’s marrying her girlfriend Hannah this summer – and even found Hannah’s wedding dress for her. ‘I definitely pick out her clothing more than she does mine. When we first started dating she was a layered-vest, ill-fitting jeans kinda gal.’

‘I have more autonomy than you make out!’ counters Hannah. ‘But I don’t think about fashion as much, so generally I’m open to subtle manipulation.’


So maybe it isn’t a question of man vs woman at all, just a game of Style Top Trumps. Besides, I’m not sure which is the more stereotypical – women dressing to please their man, or me dressing mine up like my own personal Ken doll. If anything, goes the argument in my head, I just want him to feel free to be creative and confident, to enjoy playing around with style. And the gender lines are fading; a survey by Braun last year found that men actually spend longer on average to choose their clothes each morning (13 minutes) than women do.

‘I honestly don’t think our situation is about gender,’ says Matt, when I decide the best way to ease my conscience is to sit down and ask him, with a dictaphone for prosperity. ‘In some relationships, maybe it could mean something more toxic, but for us I think it’s more like an exchange of skills. You have a stronger style sense than I do, you follow fashion more acutely than I do, you acknowledge the existence of trends…’

‘How do you feel about trends?’

M: ‘Er. I haven’t quite found a way to factor them into the way I choose to dress myself. I’m a bit wary.’

L: ‘Is that because you don’t want to waste money on things you’re not going to wear?’

M: ‘Yeah, I think a huge amount of my fashion sense is dictated by money. I like to know I’m going to wear something until it falls apart. I like to get maximum value out of it.’

L: ‘But you might get hit by a bus tomorrow!’

M: ‘Why would I want to get hit by a bus in a new coat? It’d get dirty.’

L: ‘Fair point. So you don’t feel emasculated or undermined when I help you choose things or give you tips?’

M: ‘Not at all! I think it’s generally really helpful. I buy things with you that I wouldn’t normally buy and then I learn to like them. You broaden my horizons. I don’t think there’s anything you’ve encouraged me to buy that I just don’t wear… [thinks for a bit]’

L: ‘…the boots?’

M: ‘Oh. Yes. The boots. But hey, buying those boots really sent me into an economy drive. They inspired my financial stability over the last five years.’

L: ‘So in a way, spaffing £125 on those boots SAVED you far more than they cost?’

M: ‘I think so. I genuinely think so.’

L: ‘So then fashion wins??’

M: ‘I didn’t say that.’

Like this? Then you might also be interested in:

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Follow Lauren on Twitter @LaurenBravo

This article originally appeared on The Debrief.

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