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Can real men wear flares? This season’s trickiest looks tried and tested

How to wear: flares, with and without spangles

Fashion is a fickle mistress. One season, she wants you in grey flannel and brogues, the next, kimonos and a man bun. Sometimes her demands are easy to follow: “Buy a shearling jacket!” she’ll say, or “Chuck out your knitted tie immediately.”

More often, though, her ideas are strange, even sadistic – like tuxedo shorts. To help you save face over the coming months, I am roadtesting some of the trickier trends, to see which are worth your time and which will make you look like a big plonker.

First up are flares, part of the wider 70s vogue. Flares are on a slowburn comeback, seen on the catwalk at Gucci, Valentino, Raf Simons, Marni and more. The argument for flares is that they are leg-lengthening, and “fun”. The argument against is that they are horrendous. I wore them in the 1990s, and I still remember the dampness seeping up my calves, from frayed hems that swept the pavements, drinking up all the rainwater.

It’s going to be hard, figuratively and physically, to get men out of skinny jeans, which I’ve been wearing for years now, addicted to their edgy sharpness and rock’n’roll kudos. But fashion abhors stagnation, which is why I’m reluctantly investigating Topman’s new, Woodstock-inspired collection of flares, tassled jackets and outsize flower-power prints.

‘My friend says, “You look worse than I thought you would.”’ Photograph: David Levene for the Guardian

I head out on to the street wearing a green T-shirt emblazoned with a red “MEXICO” that’s tucked into roadie flares. Flares accentuate your curves, and I feel, frankly, voluptuous as I step into my local newsagent’s. Screw the thigh gap: in these, I don’t even have a calf gap.

The shopkeeper doesn’t react in the slightest, but then he never does. Perhaps I look… OK? I check myself in the reflective surface of the milk cabinet. No, I do not look OK. I look uncool, but in a rather quiet way.

It’s time to go nuclear. I return home and swap hippy for disco: wavy blue and orange short-sleeved shirt, pastel green flares with foil spangles. The look is somewhere between eight-year-old Michael Jackson and 80-year-old Florida retiree. On the bus, people look at me with expressions of pity and concern. This is better.

I’ve arranged to meet some friends at a cafe. I stride in with a pronounced strut, because when you’re wearing Lurex flares, there’s no sense going in half-dipstick. It feels as if Boogie Wonderland should be playing. My friend Catherine, who has been looking forward to mocking me, stands up sharply, hitting her head on a lamp. “You look worse than I thought you would,” she says.

“You’re like a character from Scooby Doo,” a waitress laughs. I don’t mind the top, which has a breezy insouciance. The trousers, though… it’s hard to say what the worst thing is: their crotch-accenting tightness? The colour? The itchiness of the spangles? The fact that I am wearing spangles at all? The £100 price tag? “Wear them next to an open flame,” my friend Tom suggests, “and you’ll find out what the worst thing is.” These are nightclub clothes, designed to shimmer under lights.

I walk home like a bell-bottomed sailor, the wind whipping the fabric between my legs like a loose jib. I feel profoundly miserable.

I know that the high street lags behind the catwalk, and that men change their dress habits slowly, so it might be five years before we chuck out our skinny jeans. But even that distant thought makes me melancholy.

How to wear a boilersuit

‘I can’t get enough. It feels like pulling on a superhero outfit.’ Photograph: David Levene for the Guardian

We’ve all been there. You catch sight of a man changing a septic tank, or pollarding a row of sycamore trees, and find yourself inexplicably drawn to his overalls. “Excuse me,” you say, half-embarrassed, “I couldn’t help noticing your suit. Who’s your tailor?”

OK, I’m lying. That would never happen. If you’re around a man in a boilersuit, it’s often because you are also a man in a boilersuit, or because there has been a large mechanical failure in your environment. These are not generally occasions that call for couture.

The garment’s anti-fashion credentials are, however, exactly what the fashion world is attracted to right now. The durable workman’s one-piece is the definition of no frills, function-over-form practicality, part of the vogue for utilitarian design.

Dressing up as a rat catcher is either a bravura demonstration of the industry’s egalitarian impulse, or its ultimate piss-take, depending on your perspective.

To be fair, the catwalk version isn’t about dressing as a mechanic, or a Ghostbuster. We’re talking versatile, slimmer cuts, closer to flight suits. The Hermès autumn collection features a classy, belted one-piece in navy, while Louis Vuitton went for hot pink, and another in heavily riveted denim (the model wearing that one looked like a Pearly King about to head off into space). You’ll probably want to go for something plainer, in a nice fabric.

As I step into a black linen boiler from Whistles (who, in the world of high-street playsuits, are number onesie), I note with apprehension the drop crotch and slight bagginess around the belly. It feels like an all-over nappy, for someone who’s given up on life. But at least I’m not in hot pink, I tell myself, as I head for the metropolitan environs of King’s Cross station.

The reaction from strangers is pretty good. “Nice jumpsuit,” a passing woman approves, seemingly without irony. This is the first time I have ever been approved of in the street. I grow in confidence, which is the key to wearing anything interesting.

As it turns out, several women approach me. For them, the onesie has long been a fashion staple. “Is it single or double zipper?” my friend Alice asks. Single, I tell her. “Have fun in the bathroom,” she sings, which is not a way she’s ever said goodbye before.

Later, I discover what she means: going to the toilet requires laborious undressing, forcing me into a cubicle to zip myself down. The suit has excommunicated me from the urinal fraternity. “You end up more or less naked every time you need a wee,” female friends sympathise.

Yet I find I love the look. I like the chunky silver zips and the ersatz hammer loop. Footwear is crucial. I style it up – with turnups, a pop of red T-shirt, gleaming white plimsolls. There’s something cheerful about a boilersuit. It has dynamism, a certain ready-for- anything panache.

The next morning, I find myself reaching for my jumpsuit again. I just can’t get enough: it feels like pulling on a superhero outfit. I want to stand astride things, throw a conquering leg over rocks, pose on a billboard, silhouetted against the sky. I know nothing of pipes, will never jump from a plane, yet this simple garment has given me a glimpse of what it is to be a man. And strangely, by making me take sit-down wees, what it is to be a woman. Now that’s what I call versatile.

How to wear dance chic

‘I am in shape, but tired from dancing’ is the double-pronged vibe you are attempting to pull off.’ Photograph: David Levene for the Guardian

How can you tell when someone’s just been to a dance class? They will tell you. Frequently, under any pretext. (“Oh, yeah, the Richard III car park? That’s around the corner from where I do street dance.”) This look, known as off-duty ballet, is a visual version of the same thing, with the bonus that you don’t actually have to take a dance class; merely wearing these clothes implies you’re the sort of person who would. It’s the millennial equivalent of legwarmers.

The actual elements are less important than your body language within them: slouch is key. I try out Zara’s interpretation: a scoop vest with throw-on cardigan, drawstring trousers and sandals. “Think comfort with a side of sexy,” advises my friend Helen, who knows about these things. “Unbuttoned, rumpled, artfully dishevelled.”

Rumpled and dishevelled come easily. This is exactly how I dress when things aren’t going great. The idea is to look like a dancer between classes, flush with endorphins. This requires an ostentatious physical ease, sitting backwards on chairs, leaning against walls and suchlike. “I am in shape, but tired from dancing” is the double-pronged vibe you are attempting to pull off.

It helps if you are in shape. Billowy fabrics look heroic when you’re tall, toned and only ever sweat lightly. That’s not me. I had to work to get this body, and that work involves 13-hour days writing at a laptop, eating Monster Munch.

Time to give this look a whirl on the streets. Linen slacks are awesome if you’re slobbing around Goa on a gap year. In Elephant Castle, they are ridiculous. It is 9C outside, which, when you account for the wind chill factor of April in the UK, is actually -50C. My chest is completely exposed. Is there anything more aesthetically pathetic than an unfilled male vest? “I can see your whole nipple,” my friend Will tells me, almost angrily. On the plus side, the look is easy to pull off. “You just look like you, but douchier,” he concludes.

I begin to notice other people’s workout clothes and what they communicate. Gym bunnies in streamlined Lycra, essaying monastic self-discipline. Mud-spattered sports players, hardy and sociable. My dance and yoga energy is looser, laid-back. The outfit feels like a walking rebuke to those in suits – sellouts! – with their Netflix and their 9-to-5. I picture a new me, starting each day with chai tea, t’ai chi and mid-morning Bikram. A douchier me, sure, but attractive. I could loll around at parties, telling girls, “Yeah, maybe I went to art school, I don’t remember.”

I droop around south London, trying to look sexy but comfortable, showing people my chest hair. There are no takers. I see how this could work, at the weekend, but it makes me feel a bit swamped. “You have no job?” says the owner of my local cafe, in response. I pull a few lunges next to a performance dance college, hoping the students smoking outside notice and accept me as one of their own. I have worn a red headband to dress the look up a bit, which turns out to be a mistake.

“Wax on! Wax off!” shout some nearby workmen gleefully, which means I look like the Karate Kid.

“Where’s Ken?” yells a cycle courier, which I take to be a Streetfighter II reference.

The dance students decide to smoke elsewhere. But, hey, at least they noticed me.

***

The experiment over, what have I learned? It’s been a week of ups and downs. Mainly downs. I’ll definitely be buying a boilersuit, if only to convince people I have a job. Ballet chic has potential, because it’s easier pretending to be healthy than actually being it. And I’ll be stockpiling all the skinny jeans I can find, while burning any flares on sight. I urge you to join me.

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