What do an A-list actor in a letterman jacket, a Prince with a trendy backpack and a rock musician with a stack of leather bracelets all have in common?
They might argue it’s a shared sense of style, but these men in their 50s – and beyond – have fallen into the trap of trying to remain youthful by dressing like teenage boys.
Bradley Cooper, 51, Prince Edward, 62 and Johnny Depp, 62, are all guilty of ‘tryhard’ fashion mistakes that also include skinny jeans, ill-fitting beanies and trendy trainers – more suited to your son than your midlife husband.
Given the epidemic of women complaining that their husbands have turned into miserable men who don’t care about their appearance, making an effort in the style stakes is to be applauded.
But it can easily tip into the territory of mutton dressed as lamb, and likely to leave the women in their lives equally unimpressed.
‘Style in your 50s should feel effortless, not like you’re chasing trends half your age,’ Lisa Talbot told the Daily Mail.
‘The key difference? Confidence and refinement. When certain pieces feel forced or disconnected, they can tip from stylish into “trying too hard” territory.’
Lisa explained that men of this era need not sacrifice fun and experimentation, but rather be more intentional with their choices.
‘Great style in your 50s isn’t about dialling things down, it’s about editing,’ she added.
‘When you remove the noise and focus on fit, quality, and cohesion, you don’t just look better… you look effortlessly confident.’
DISTRESSED SKINNY JEANS FROM ANOTHER ERA
The noughties were known for our obsession with denim – the skinnier and more disheveled, the better.
However, that era is now long gone, with modern tastes favouring looser silhouettes and a focus on good fabric.
‘Heavily ripped, ultra-skinny jeans can feel dated and try-hard rather than youthful,’ Lisa advised.
‘Swap them for a straight or slim-leg jean in a dark or mid-wash, modern, flattering, and infinitely more polished.’
BACKPACK THAT DOESN’T FIT THE REST OF YOUR OUTFIT
A backpack is a lifesaver when you’re on the go – but sometimes, it can distract from the rest of your ensemble, especially in more formal settings.
‘Backpacks can feel overly casual when paired with smarter outfits, creating a disconnect that looks unintentionally awkward,’ the stylist said.
‘A structured leather holdall or a sleek briefcase instantly sharpens your overall appearance.’
LETTERMAN JACKET
Letterman jackets have come into fashion following a myriad of 80s reboots set in American high schools (a la Stranger Things).
However, Lisa suggested that while they certainly have ‘nostalgic appeal’, it’s a look that ‘doesn’t quite translate in later life’.
She shared: ‘A tailored bomber or a smart casual jacket offers the same relaxed feel, but with far more sophistication.’
TRENDY TRAINERS THAT LOOK OUT OF PLACE
Practical and comfortable trainers can feel like an easy option to go for – especially if they’re trendy.
However, Lisa warned that they can make or break an outfit.
‘Fashion-forward trainers can look forced if they don’t align with the rest of your outfit,’ she explained.
‘The trick is balance, clean, minimal trainers in neutral tones will always look more sophisticated than anything overly “hyped”.’
STACKING LEATHER AND BEAD BRACELETS
Men in their 40s and 50s are very likely to have a beaded or leather bracelet. But Lisa explained that, unless there is a cultural or sentimental value attached, they risk looking of looking out of place.
She said: ‘Layering multiple bracelets can quickly look cluttered and overly styled, especially when it feels like each one is competing for attention.
‘Instead, opt for one quality piece, a classic watch or a single understated bracelet for a more considered, elevated look.’
ILL-FITTING BEANIE
Beanies come in and out of fashion every couple of years. But Lisa said that men must tread carefully, as this hat can look better or worse depending on proportions.
‘Beanies can work, but only when they’re well-fitted and styled with intention,’ she shared.
‘Slouchy, oversized versions can look like an afterthought. A more structured knit or even a classic flat cap can feel far more age-appropriate.’
OUTDATED ‘FESTIVAL’ HATS
The bohemian comeback in the 2010s saw hippie-style outfits and wide brim hats come back into fashion. However, now, they can simply feel ‘costume-like’, the stylist advised.
Lisa said: ‘Coachella-style hats had their moment and it was nearly a decade ago.
‘If you enjoy hats, stick to timeless shapes like a well-made fedora or a classic panama.’
