THE JOURNAL

From left: Aaron Levine, photograph courtesy of Aaron Levine; Armando Cabral, photograph courtesy of Armando Cabral; Richard Biedul, photograph by Valentina Valdinoci/launchmetrics.com/spotlight; Aaron Levine, photograph courtesy of Aaron Levine
“It’s not the years, honey. It’s the mileage.” Perhaps you’re nodding in agreement with these words from the plucky archaeologist Indiana Jones (played by a radiant Harrison Ford, then 38) after being told he wasn’t the same man he was 10 years prior. It’s fast living that leaves its mark – and we all feel the same inside at 20 as we do at 40. But consider this: come 2026, we’ll be as distant from 1981, the year Raiders Of The Lost Ark was released, as the film was from 1936, the year it is set. So, maybe it is also the years.
The big 4-0 has long been a significant milestone. But for older millennials – “geriatric millennials”, if you really must – plunging head-first into their fifth decade on earth, the expectations for how to behave and how to dress as they enter middle age are somewhat blurred. For generations before, 40 was, well, old. Well old, in fact. Think dads with “proper” jobs, returning home in suits and ties. And yet, for 40-year-old men today, rocking beanies, hoodies and the latest sneakers, 40 still is – feels – quite young. Right?
All we’ll say is that there will come a moment that turns all this on its head. It could even be the first grey hair on your head. When a cultural reference that everyone used to get suddenly doesn’t land with younger colleagues (see Indiana Jones, above). Or that increasingly rare night out, when you end up someplace where the music is too loud and everyone else is half your age – and wearing the same clothes that you wore at the same point in your own life. Fashion’s 20-year cycle has lapped you. The world has moved on. Only, don’t panic – take a step back, a deep breath and get some perspective.
“When I see younger generations embracing styles I wore in my twenties, it’s a reminder of how timeless good design can be,” says Armando Cabral, the model and founder and director of the eponymous shoe brand. “It doesn’t make me nostalgic – it just reinforces that personal style is about making things your own, no matter the decade.”
So, before you rush out on a midlife shopping frenzy of TikTok-core duds in a desperate bid to stay relevant, here’s what you need to know about dressing in your forties. The good news is that all that experience should come in handy.
01. Accept your new reality
“By your forties, you should have a solid understanding of what works for your body, your fit and what aligns with your personality,” Cabral says. Lean into this.
“You’re the brand that you want to be perceived as,” says Farid Hounkponou, Personal Shopper at MR PORTER. “You’ll inevitably be more selective, investing in pieces that align with your values and stand the test of time. The key? Effortless confidence.”
The fortysomething designer, art director and menswear consultant Aaron Levine says that, by this stage, you should be “confident of the tools you have in your toolbox and your ability to use them”. “For the most part, I wear thoughtfully designed and well-made staples,” he says. “Can’t go wrong. I try to do my best to eliminate the flash and the trash and just wear easy, comfortable things that allow me to feel like myself.”
“Good shoes, a classic watch, the best-quality sweatshirt, a navy blazer,” says Johnny Davis, style director at Esquire UK. “You start to do the cost-per-wear thing, and these will always win.”
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02. Find a tailor
“Men can get complacent as they get older, thinking that spending a lot of money on a good-quality item is enough,” says Shakaila Forbes-Bell, fashion psychologist and author of Big Dress Energy. “Incorrect. You have to get things tailored. Not only will you look and feel better, but studies show that people are more receptive and think more highly of those wearing well-fitting clothes.”
“Clothes should complement your body, not fight against it,” Cabral says. “Poor fit can age you more than anything else.”
“Alan Flusser, the author of Dressing The Man, says that style is 90 per cent fit and colour,” Davis says. “You just need to get that right.”
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03. Do denim
That old edict about jeans on men over 40? Put it in the bin. “You totally can wear jeans,” Davis says. And while we’re not stopping you from trying out the buzziest trend, you probably already know if the bootcut suits you or not from the last time it did the rounds. Which is to say that if you’ve found a style that works, why not stick to it? “The artist Takashi Murakami has amazing style,” Davis says. “He loves a baggy pair of jeans.”
Davis adds a caveat: “I did once ask a colleague why he always looked so well turned out, and his answer was, ‘I just don’t wear jeans.’ So, if you want to appear ‘smarter’, then that’s a trick.”
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04. Hit below the belt
Whether you opt for jeans or not, Davis identifies the lower half as the area where what you wear can have the biggest impact. “It’s easy for men to forget their trousers,” he says. (No, not like that.) “And jackets and jazzy shirts get all the attention. But the opposite is cooler – an amazing pair of pleated trousers and a T-shirt looks great.”
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05. It’s not just trends that change…
For many of us, the reality of hitting 40 is that our bodies begin to change, too. And getting dressed in the morning might be a constant reminder of this fact.
“Staying true to your style is important, but rigidity isn’t the answer,” Hounkponou says of dressing in your forties. “Adaptability is. As our bodies change, it’s essential to have a core selection of well-fitting, high-quality pieces that consistently work. Adjustments will be necessary, but they should always align with what makes you feel your best.”
It’s not just what we wear that needs continual maintenance. We also need to work on the way we think about ourselves.
“Self-talk is a great way to address changes in your body in your wardrobe,” Forbes-Bell says. “Our go-to response, particularly when we’ve become more sedentary and may have gained weight, is to speak negatively about your body and claim you have nothing to wear.
“Psychologists Vanessa Patrick and Henrik Hagtvedt discovered that replacing the words ‘I can’t’ with the words ‘I don’t’ can positively impact goal-directed behaviour, giving a sense of control,” Forbes-Bell adds. “So, instead of saying, ‘I can’t wear this because I hate how much my stomach has grown,’ you’ll say, ‘I don’t want to showcase this part of my body today, so instead, I’ll wear something that highlights a part I do like, like my arms’. This self-talk allows you to see the benefits of your wardrobe that you can be blinded to when you’re fuelled by self-loathing.”
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06. The clock is ticking
Maybe it’s the increased awareness that time is finite, but as watch expert Chris Hall notes, the forties are the “business years” when it comes to investing in a watch. “It’s the period when men who haven’t yet done so feel that imperative to buy a proper grown-up one,” he says. “You want to avoid any insinuations of midlife-crisis shopping and buy something properly classic. It still needs to suit you, so that doesn’t mean reverting to a big dive watch because it feels like the right thing to do. The watch for your forties might be a Cartier, a Chopard or a Jaeger-LeCoultre.”
For experienced collectors, Hall argues that this is when you should look to consolidate and upgrade. (He argues the case for trading up and pulling the trigger on that long-term, Wish List timekeeper here.) “Put a couple of watches aside and focus on what you really enjoy,” he says. “That could be anything from a very serious chronograph from IWC to your first perpetual calendar. Or this might be when seasoned watch buyers graduate to rarer independent makers – you will start looking at Ressence and H. Moser with new-found interest.” The world is your Oyster Perpetual.
“A great watch will never be wrong and is the one item of clothing that will at least hold its value, if not increase,” Davis says.
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07. Dip into the archives
“Just because you haven’t worn something in a long time doesn’t mean it’s not for you,” Forbes-Bell says. “It’s easy for us to lose ourselves. Often, we can find that version of ourselves that we once lost, in our wardrobes.”
By this stage of your life, you’ll also have a better gauge of which items have staying power. Use that nous to inform any subsequent purchases.
“Trying too hard is a big misstep for most folks,” Levine says. “If you’re truly lost and unsure of what direction to take, keep it like a haircut. Find a picture of the haircut (outfit) you like, then search your closet for already existing items that could complete this. If you’re missing things, you can at least narrow the search.”
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08. Know yourself
“As per Tom Cruise’s walk-in wardrobe in Risky Business, there’s an idea that men – it’s always men – will have settled on their ‘look’ and they can simply reach for it every morning, like a uniform,” Davis says. “It really does seem to take a few decades to work that out. That might be, ‘I’m the suit guy’. Or it might be, ‘I’m the guy who only wears navy’.”
Think of this as finding your groove rather than being stuck in a rut, Davis says. “There’s liberation in being freed from the relentless cycle of fashion, of stepping out of it.”
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09. Just don’t give up
“The worst thing you can do is give up on fashion altogether,” Cabral says. “Style is a reflection of how you present yourself to the world – it should evolve, not disappear. That said, blindly following every trend isn’t the answer, either. The key is balance: incorporate modern elements that feel natural to you, without losing your personal style.”
“Jumping on trends is unnecessary, expensive and clownish,” Levine says. “It just smells fraudulent.”
“No one cares what you wear,” Davis says, is the key lesson that his forties taught him. “Wear whatever makes you happy. No one is judging you. Unless you’re turning up to a funeral in a tracksuit, then really, get over yourself.”