THE JOURNAL
Spare a thought for the ageing millennial man. Generational elders like me (43-and-three-quarters at the time of writing) are entering the arrivals lounge for middle age and, frankly, it’s carnage. Burning out amid the embers of back-to-back financial crises, pandemics and sociopolitical upheaval, one survey found that 81 per cent of us can’t even afford a midlife crisis. Other research suggests we’re simultaneously careening towards a cliff edge of accelerated ageing, which is just great.
If all that wasn’t bad enough, there’s also trouble in the trouser department. The guy who wore baggy trousers in the 1990s and spray-on jeans in the 2000s is hitting middle age at a time when legwear is a free-for-all, a billowing spectrum that stretches from millennium-bugged skater pants to born-again skinny fits. For a generation known for anxious decision-making, it’s just too much. Our fathers didn’t have this kind of cognitive load to deal with. Unless you were a part of a very specific subculture, previous generations largely had a style blueprint to follow.
“We see our contemporaries experimenting with style in ways that the guys who came before us did not”
“What we saw in previous decades was, in general, trends were for everyone,” says the menswear trends forecaster Edwin van den Hoek. “Now it is much more diverse and there are some trends that are more suitable for younger or slimmer guys.”
At the same time, he says, today’s middle-aged men are the first post-Beckham generation to reach the top of the hill. From this vantage point we see our contemporaries experimenting with style in ways that the guys who came before us did not. Over there you’ve got Pedro Pascal in a pair of parachute pants. And see him? That’s Colman Domingo in flared tuxedo trousers.
“There’s a lot more self-expression going on with this generation,” van den Hoek says. “A lot of men are focusing much more on their physique. Maybe there’s more vanity also.”
Of course, away from the red carpet, there’s a microfilm line between vanity and hubris. I want to look like I’ve made an effort, but nobody wants to look like they’ve tried too hard.
“Was the flowing silhouette my generation’s version of a red sports car?”
Case in point: I recently invested in some new denim, midlife inflation having hit the midriff. My days in a slim 511 are way behind me, but I wanted to experiment at the other end of the spectrum, dipping a leg into something wider, generous and comfortable. The self-doubt kicked in immediately. Was I trying to look younger than I am? Was the flowing silhouette my generation’s version of a red sports car?
I retreated to the neutral ground of a straight-leg fit. To be fair, that’s a good comfort zone for guys my age, says menswear consultant Luke Hodges. “A straight or slightly wider straight-leg fit is the safest, most versatile middle ground for most men, especially if you’re not looking to make a big statement,” he says. “It’s a fit that works with almost everything in a modern wardrobe. And it avoids the extremes on either side.
“That said, I’m personally adding more wide-leg trousers into my wardrobe – and it’s opened up outfits I never could’ve put together in slimmer silhouettes.”
So, how should you adjust your trousers? Below, we offer the skinny on how to wear the most flattering fits.
01. Think about rise as well as width
Whatever the width of your trousers, rise – as in the length from crotch to waistband – is doing a lot of work, Hodges says. “A slightly higher rise really helps the silhouette, particularly with a wider leg as it lengthens the legs and avoids that low-slung 1990s skater look many of us wore in our youth.
“If you’re going wider, I’d keep everything else crisp, a clean wash, no rips or heavy distressing, and a simple, unfussy design. That stops a looser fit from looking sloppy.”
02. Don’t dive in at the deep (wide) end
If you’re thinking about going baggier, do so gradually. “Don’t jump straight from slim to full skater-wide because it’ll look weird to you initially and feel like a costume,” Hodges says. “Keep the rise high, because a low rise with a baggy leg instantly throws you back to sixth form.”
Also consider how the rest of the outfit balances out. “If you’re wearing a wider trouser, think about what’s happening up top. A slightly fuller jacket or a knit with a bit more body can help the silhouette make sense.”
03. Match your footwear
“A lot of guys forget about footwear,” Hodges says. “Baggy or generous cuts often need a chunkier shoe and sometimes even the right belt or outer layer, to carry the fuller shape of the trouser. If you try a wide leg with the same slim T-shirts and lightweight shoes you wore with skinny jeans, you’ll probably look in the mirror and feel like something’s off. Make sure you’re preparing the rest of the outfit for that shift in proportion.”
04. Top-and-bottom your fit
Just as a higher waist can be flattering and lengthen the leg, consider the hem of your trousers, too. “We’ve moved away from aggressive ankle crops,” Hodges says. “No break is still a great option, but especially for wider cuts, a fuller hem and a soft break work really well. You don’t need pools of fabric, but a gentle break on a wider leg looks considered.”
05. Get a tailor
As ever, find a good tailor if you need one. “Even with wider cuts, you still want the hem and overall length cleaned up so you’re not swamped by fabric,” Hodges says.