THE JOURNAL

From left: Mads Mikkelsen at the Cannes Film Festival, 17 May 2023. Photograph by Pascal Le Segretain/Getty Images. Pedro Pascal at the SNL50 in New York City, 16 February 2025. Photograph by TheStewartofNY/WireImage via Getty Iamges. Daniel Craig at Chateau Marmont, Los Angeles, 4 January 2025. Photograph by Charley Gallay/Getty Images for W Magazine. Colman Domingo at Caesars Palace. Las Vegas, 3 April 2025. Photograph by Jerod Harris/Getty Images for CinemaCon
Those of us who have been around long enough to be able to say we have “grown up” with Paul Weller might have noticed a shift in the kinds of questions the former The Jam and The Style Council frontman gets asked in interviews these days. In place of earnest enquiries about the enduring appeal of Colin MacInnes’ Absolute Beginners or left-wing politics, there is now an even greater propensity for profile writers to ask about the way Weller looks.
The hair, obviously. But all those clothes, too. The implication being that there’s something a bit sad about someone his age (he’s 66) who still cares enough to polish his shoes and iron his shirts.
A case in point: Weller was recently asked if he kept a pair of Crocs by the front door, for putting the rubbish out. “No way,” he replied, firmly. “No slippers, either. I wear trainers in the house. But only adidas, old-school adidas. One has to keep up some sort of standards.”
If there were a single piece of advice we could give anyone entering their sixth decade – or beyond – it is that. One has to keep up some sort of standards. It’s not even that difficult. And you may not actually need to buy anything new to do so. To that end, we’ve assembled a mini style council of our own to provide you, the man now comfortably past the midway point, with an indispensable guide to looking your best at 50 – and beyond. Here’s what they said.
01. Know yourself
In many respects, your sense of style should have evolved and refined over time. But also, it might not have changed at all. And that’s fine, too.
“Dressing in one’s fifties is no different than one’s forties or twenties,” says Julie Ragolia, the stylist for Pedro Pascal, who just turned 50, and Mads Mikkelsen. “It’s about one’s state of mind and attitude towards life. We don’t age into boredom. We don’t age into rules. We age into a deeper understanding of who we are as humans, which should grant us all the more freedom to wear whatever we want. And, hopefully, by the age of 50, one has the finances to support whatever said wishes of expression may be, so there is even less issue to compromise on personal aesthetic.”
02. Go for the easy wins
“Once you get to our age, you start to become slightly invisible,” says Campbell Carey, creative director and head cutter at Huntsman, on Savile Row. “Maybe you’ve had kids. You start to get a little bit long in the tooth. You’ve got to make an effort. You’re starting to think less fast fashion and more key pieces that you can build a wardrobe around.”
Catherine Hayward, fashion editor at The Times Luxx Men and former fashion director of GQ and Esquire, thinks making an effort starts before clothes – with the basics. “A proper haircut,” she says. “It’s really nice when you see a man and you think, ‘You’ve got really neat hair, and you’ve just clipped your beard’.”
Taking care of your nails, moisturising your hands and polishing and reheeling your shoes are other easy wins, Hayward says. “It’s just really simple things like that, and you look really well cared for.”
The Strokes used to have a band rule that they’d dress every day as if they were performing a show, even if they weren’t. Jarvis Cocker has explained that he always wears a suit and tie, “because you never know who you’re going to bump into”.
03. Get off the trend train
One of the benefits that comes with being an older guy is that the days of chasing the latest looks or trying to keep up with the hypebeasts should be behind you. By now, one hopes you’ve found the kinds of clothes that suit you and aren’t “changing it up” each season. Frankly, that should come as a relief.
“Trends are something one should avoid,” says William Gilchrist, the stylist who has worked with the Rolling Stones, Cillian Murphy and Rami Malek. “There’s a certain age where one should have developed a certain level of style. Be it personal, be it terrible, but at least be it your own.”
We all know that the barriers have come down between age groups. But if you’re dressing like your teenage son, something has gone wrong.
“That whole concept of ‘just chuck anything on’ won’t do,” Gilchrist says.
04. Make sure it fits
“For me, the best thing to consider about your wardrobe is fit,” Hayward says. “One of the most basic things I do when I’m styling is I go to someone’s wardrobe, with the person, and just get them to try it all. Does it fit them? Most of the time, no, it doesn’t.”
This is the part where we’d normally remind you about changing body shape. That you’re not 25 anymore. But if that usually implies you might be carrying a bit of extra timber around the midsection, Carey says that this isn’t necessarily the case. “People at our age are starting to think, ‘Right, hang on a minute. I’ve only got so many years left; I’m over halfway,’” he says. You start thinking the long game. Everything in moderation.”
Hayward says that the my-clothes-don’t-fit problem may be down to something as basic as the difference between how the genders have traditionally shopped. “When I go on shoots, an anomaly for men in general is that when you ask them what size they are, they have no idea. So, just measure yourselves! Carry your measurements around with you.”
(Also, she says, remember that being “waist 32” in a low-slung jean probably doesn’t mean you’re also a “waist 32” if you go to a tailor.)
05. Well-fitted doesn’t mean tight
“It’s actually the opposite,” Carey says. “A tight suit looks worse that one that’s roomy, you know?”
Both Carey and the designer Oliver Spencer sing the praises of pleated trousers for the more senior age brackets. They give more room through the leg and comfort when you sit down. Hopefully, your life has panned out that you’ve got at least a bit more money in your fifties than you had in your twenties. Carey says that may be reflected in your superior choice of cloth. (“If you’re at the top of your game, you’re now ordering flannel from me. Blue-charcoal flannels are just so elegant.”)
You don’t need us to tell you that skinny jeans are out. Spencer would throw the “skinny shirt” in the bin, too. “That’s a really bad faux pas,” he says. “Skinny shirts that you used to wear into work when you had an eye on a co-worker, and you used to want to show off your muscles. But maybe now the muscles aren’t there. And, basically, it looks bloody awful. Loose, relaxed, boxy – that’s where it’s at.”
06. Choose your armour
Double down on the colours and styles that suit you. For many of us, that means “50 shades of navy”, Spencer says. And there’s nothing wrong with that.
“I stick to navy, grey, tan, bottle green – that whole palette,” Hayward says. She approves of the notion of “a uniform”. “You just build up very few things without actually having to think about it.”
You may have decided you’re the “navy crew-neck guy” or “the suits guy”. Gilchrist adopted the DB – fashion-speak for double-breasted suit – as his style signifier some years back. “For me, they’re like a sartorial hug,” he says. “I think of it as armour. Whatever I do, wherever I go, there is one in my luggage, or I’m wearing one.”
This doesn’t necessarily mean you need to be dropping thousands of pounds on Savile Row. Gilchrist’s DBs are almost always soft and unstructured. Some are 20 years old. Some he’s picked up in markets for next to nothing. “Most of them go in the washing machine,” he says.
07. You can still have a bit of fun. To a point
Spencer isn’t averse to adding “an accent” – ie, one slightly jazzier item – in the form of a tie, a hanky or a pair of socks, to give a burst of character. “Logos should be avoided,” Hayward says.
Tread carefully with loud colours and prints, too. Texture, on the other hand, is your friend. “A textured merino-wool sweater with a textured wool jacket looks really good,” Hayward says. “You can keep it all navy, but because it’s different textures, that keeps it interesting.”
We can, of course, think of men of a certain age who look absolutely amazing in loud, clashing streetwear and clothes that were once considered the preserve of teenagers – the artist Takashi Murakami comes to mind. A fan of logo-bedecked varsity jackets, harem pants and Day-Glo sneakers, usually worn all at the same time. Murakami is 63. Or think Colman Domingo, 55, or Pascal, 50. Pharrell Williams, 52, is another one. But here, Hayward points out a key difference between them, and the rest of us.
“Pharrell has the swagger to wear something tight, with shorts and a wacky hat – and he looks cool,” she says. “But he’s a multimillionaire who has the responsibility of looking the part for a red-carpet shot. In general, you don’t want to stand out for looking kooky. You want to stand out for looking stylish and chic and low-key.”
08. Ultimately, it’s all about respect
“Clothes give you a sense of poise,” Gilchrist says. “They allow you to carry yourself differently and handle yourself differently. It’s the idea that you are going somewhere and you are doing something and you need to respect that. When the concept of ‘dress-down Friday’ came in, I just thought, ‘What about “make an effort Friday”?’”
And there’s always a place for sneakers. “Trainers need to be used for sport,” Spencer says. Or, at a push, putting the bins out.
The people featured in this story are not associated with and do not endorse MR PORTER or the products shown