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Being a 50-something is tricky. Midlife crises may be largely complete, greying hair and ageing successfully navigated. Yet you’re not quite old enough to ignore the huge social and fashion changes under way.
If you’re anywhere near my age and think you’re brand aware, or know what’s cool, you’ve either had a severe knock to the head or watched too many TikTok videos. Surely nothing about being brand aware in your fifties is remotely important. Or is it?
I’m not yet ready to surrender style in favour of making comfortable or practical choices. I think back to the time my dad ditched his Audi for a Volvo. Would I give up on designer labels and bespoke suits and shop instead at M&S where you can buy clothes in different sizes to accommodate fluctuating girth? Not this year, my friend.
But there’s something much, much worse than not looking cool, and that’s making inappropriate brand choices for your age.
Around my 40th birthday, I’d been on a significant diet and ended up in Abercrombie & Fitch. Just because something fits, it doesn’t mean you should wear it. New brands are a no. Dropping £800 on a Supreme hooded sweatshirt? The teen it’s aimed at shouldn’t be able to afford it. And although you can, you shouldn’t wear it.
Cool isn’t set in stone. Bubbly doesn’t have to be Veuve, Krug or Bolly if you have a more interesting English sparkling to serve. A watch doesn’t have to be a Rolex if you’ve decided that IWC is your thing. And your car doesn’t have to be made by Aston Martin. But you’re not going to go far wrong with any of them. Some brands have always been cool. And some, no matter how hard they try, never will be. Škoda. I rest my case.
Fashion and styles change. Sometimes a brand that’s incredibly cool becomes uncool almost overnight. Some years ago I wrote, rather proudly, about my Balenciaga sock shoes. Then, after a series of advertising catastrophes, the brand lost its lustre. Now my £600 knitted sneakers have one purpose: gardening shoes.
Does that mean every marketing change or negative review leaves you looking uncool? Think Jaguar. I have an I-Pace, time and again recommended as the best electric car if you don’t want to line Elon’s pockets. Then the company rebranded. Many slammed the exercise. Despite capitalising the G and a lot of other guffery, we’ve all been talking about it. Anyway, if the new cars are good, the advertising will be long forgotten. Which makes navigating our modern world even more complex. A good product from a poor brand can still be cool. How does that work?
When I was younger, brands were simple. You could gauge someone by their clothes — if they wore Adidas, they probably played football (or at least ran for a bus once). If they wore Levi’s, they were cool and wore boxer shorts, not pants. If they wore Clark’s, they were probably your mum’s friend’s son, and not someone you’d spend much time with. There was no ambiguity. No confusion. You just bought what worked or what your older brother’s cool friend wore.
The good news is that, according to what I hear, the 1990s are back. Many of the things I should have thrown away are back in fashion. Ralph Lauren polo shirts, moleskin trousers and rugby shirts. The other day, while rifling through my old clothes wardrobe, my other half found a Burg’s Mad Rags rugby top, 1996 vintage. “That’s cool,” they said, whipping it away to wear it. Why didn’t I know it was cool again?
Because they’re cooler than me. You don’t have to wear the right label to let people know that you’re cool. You just are or you’re not. Maybe it’s swagger, body shape or just having an eye — all attributes I lack.
But what I do know is that there’s something deeply undignified about a man of a certain age wandering around in labelled streetwear. Yes, an £848 pair of Moncler x Palm Angels sneakers look great. On the shop’s shelf.
The truth is, no one cares what you’re wearing. People have their own problems, their own lives. Their own brand-new Off-White sneakers they dropped £500 on.
They’ve already forgotten what you look like five seconds after you leave the pub. What matters is how you carry yourself. If you walk into a room in pair of Chelsea Boots that you bought for 40 quid at your local shoe shop but you own it, you can carry it off.
If, however, you enter the same room with a jacket worth the GDP of a small country and box fresh trainers that are over decorated with designer labels, you’ll be just another bewildered middle-aged bloke who’s clearly trying too hard.
So, should you be brand aware in your fifties? Yes. Should you wear new cool brands? Of course not. That’s for teenagers who still think their identity is somehow tied to the logo plastered on their chests.
I’ve lived a life, one that doesn’t require a designer bag or a pair of trainers that cost more than a weekend getaway in the Cotswolds. Sure, I’ll keep the Rolex and the Aston. They’re cool. And I’ll buy a pair of trousers at Marks and Spencer. Because M&S is cool now too — or so I heard on TikTok.
James Max is a broadcaster on TV and radio and a property expert. The views expressed are personal. X, Instagram & Threads@thejamesmax
