If you’re off to see your team play, of course you’ll wear your baseball cap! In those circumstances, it doesn’t matter if you’re five, 50 or even older: baseball caps are what people wear. However, away from the stadium – say, meeting friends for a drink – that same baseball cap can just make it look like you’re trying to hide a bald patch.
Frat boy dressing
Let’s be frank: frat boy dressing makes most frat boys look slightly ridiculous. And if it does that to a youthful, clean-shaven twenty-year-old, what is the same look going to do to you? It’s best never to be tempted – and, yes, that even includes College reunions.
Plenty of young guys wear sports clothes – sweatpants, a favorite team’s shirt, and so on – even when not playing sport or exercising. For them, the clothes emphasize their youth. On an older man, however, this style of clothing can easily look desperate, as if the wearer is trying too hard to roll back the years.
By the time you reach your 50s, you ought to have clocked that clothing trends come and go so frequently that their most obvious use is to boost the takings of designers, clothing manufacturers and stores. Moreover, you should also have learned that some trends are so awful they should never see the light of day.
The wrong cologne
Perhaps you’ve already self-selected yourself out of the Old Spice category. After all, your father and, before him, your grandfather wore it – and you’re much younger. And that’s fair enough. However, once you’re in your 50s, it’s probably a good idea to swerve fresher, lighter scents that suit neither your maturity nor your style.
Excessive use of patterns
Some people wear patterns very well indeed. However, they’re few in number and even fewer of them are found among over-50s males. If you must wear pattern, avoid looking badly put together by opting for a single patterned item, such as windowpane check blazer or a subtle floral shirt.
It doesn’t matter what sort of jeans are currently in style. Instead, what’s key – and the importance of this only increases as you get older – is to wear a style and color that suits you. This might mean a hard pass on the stonewashed Wranglers that still fit you or the designer ripped pair that catches your eye online.
At the moment, it’s fashionable to wear sneakers with just about anything. And this is an understandable trend as, apart from anything else, sneakers are often more comfortable than the alternatives. That said, if you’re someway past youth’s first flush, think hard before slipping on sneakers with your suit or other fairly formal wear.
If anyone can wear traditional golf attire and get away with it, it’s surely an older guy. However, even for these men, there are limits. On the golf course, of course, golf attire is de rigeur. However, it’s trickier to wear casually. You might get away with it for a neighbor’s barbeque but visiting your kid at college? Maybe not…
You might have gotten away with drainpipe jeans and slim-cut shirts in your teens and twenties. Unfortunately, by the time they hit their fifties, most people are carrying a few extra pounds or, at least, natural weight redistribution has altered their physique anyway. As a result, think really hard before wearing anything that shows the contours of your body.
Socks with sandals
Just no. Sure, your gnarly, hairy toes might not be your best feature but we promise your overall look is not improved by teaming socks with your sandals. Make a chiropodist’s appointment instead, get your feet into shape and lose the socks!
Unless you work in a medical setting, where crocs are often favored for their practicality, crocs are one item of footwear that shouldn’t cross your closet’s threshold. And, yes, that also means not wearing them for a day at the beach or, worse, a trip to Home Depot. Leave crocs to the young – and, preferably, to the very young.
Unless you’re a member of the British upper classes who’s setting off on a grouse shoot or a certain sort of College professor, tweed is a tricky fabric to wear. It has a tendency to make the wearer look like they’re either in the wrong place or have badly misinterpreted the dress code.
While you don’t need to restrict yourself to plain or even two-tone socks, think hard before venturing beyond the striped or the subtly-patterned. Comedy – especially cartoon-themed – socks have one possible role in the life of the over-50s man, and that’s as one-off seasonal wear at Christmas.
If your family insists on buying you novelty ties as birthday or Christmas gifts, it’s probably time to drop a few not-so-subtle hints about what you’d actually like. Novelty ties have no place in the attire of a mature man who knows what suits him and wants to be taken seriously.
No matter how cool you think you look, oversized pants, especially anything with multiple pockets or zips, are a no-no once you hit your 50s. You get a temporary pass if you’re a Boy Scout leader on a camping expedition or heading into the wilds on your Grizzly Adams-style adventure.
Camouflage print or, indeed, any clothing items with some sort of military heritage are always tricky for a number of reasons. While you can potentially get away with them in your younger years, they really don’t look good on older gentlemen – unless, of course, you really are in the military.
Yes, we’ve already covered sneakers but this old favorite deserves its own special category. There’s a good chance you moved from sneakers to Converse in the belief that the latter is more suitable for the older man. However, sad to say, there comes a point when your trusty Converses have the mark of someone trying too hard to hang on to their younger years.
Perhaps you look back fondly on the 90s as the decade of your youth. However, just because the era is currently enjoying a fashion revival doesn’t mean that you should co-opt it for yourself. Unfortunately, that bucket hat is more likely to make you look like someone who never left the decade.
Jimmy Buffet-style shirts
We’re not meaning the disparage the late, great man himself. However, what suited him is…..what suited him. On anyone else, and especially a man of over-50 and therefore “old enough to know better”, the distinctive patterned button-down shirts are a big no-no.
What do we mean by this? Well, on one hand, we mean it quite literally: it’s anything you’ll find online that’s prefixed with “Dad”. This includes Balenciaga’s Dad jeans and a whole gamut of Dad sneakers. On the other, it’s anything you associate with middle-aged Dads. Either way, the word is being used to indicate that this is something your father would have worn. Is that really your preferred style direction?
Too much black
You might think you resemble a particularly stylish Bond villain. However, in all likelihood, all that black is draining the color from your features and making you look several years older than is actually the case. Even if black is a favorite color, remember that, for most people, it gets harder to carry off as you get older.
Badly fitting clothes
You can just about get away with clothes if you’re young enough for it to look ironic or trend-led. However, the older you are, the bigger the risk that your jacket that’s too big across the shoulders and the way your belly bulges over the top of your too-tight pants makes you look impoverished or as if you just don’t care.
Anything in need of repair
Perhaps you’re not handy with a needle and thread but, frankly, anyone can sew on a button. Larger repairs – ripped seams, a turnout that’s come down, a moth hole in a favorite sweater – might need more specialist assistance. If you’re lucky, you’ll have a family member who’s willing and able to take on the task. If not, find a good tailor and pay to have the repair done. By 50ish, there’s no excuse for leaving these things.
A good t-shirt is an essential part of a good outfit. Most slogan t-shirts, on the other hand, advertise political affiliations or suggest the wearer has a rather dubious sense of humor. Neither are particularly appropriate on the older man. Sharing either your politics or your humor is almost always best done through conversation rather than turning yourself into a walking billboard.
No-one who doesn’t share your bedroom or your gym locker room needs to see your underpants. If that isn’t a big enough clue that low-slung jeans out out for the over-50s man, we don’t know what is. Buy a belt, a pair of braces or, preferably, a pair of jeans that fit and keep those underpants private!
Prominent or over-sized logos
The point to remember about logos is that, by wearing one, you are essentially advertising someone’s business. Perhaps that doesn’t matter to you although many people get increasingly uncomfortable with the idea as they get older. Even if you don’t mind the advertising connotation, you might not like the way that visible logos are, in some way, providing validation to the wearer.
Workwear worn casually
Really the only time that it’s acceptable for workwear to make an appearance in casual society is when you’ve gone straight from work to some other event. Preferably that other event will be work-related because, if it’s not, ask yourself whether you really couldn’t have found space and time to make a quick outfit change. Staying in your work clothes – especially a recognizable uniform – suggests you really can’t be bothered to make any effort.
Untucked dress shirts
Our clothes say a lot about us, and often more than we realise. Little things matter – and these “little things” can include an untucked dress shirt. On any man, but especially an older one, an untucked dress shirt conveys a certain personal sloppiness and a suggestion that this is a person who can’t be bothered to attend to the small things that make a real difference.
Getting a neckline right can be tricky at any age. What suits one person’s body may look all wrong on someone else. However – and we do appreciate that it’s a generalization – v-neck t-shirts need treating with particular caution when it comes to the over-50s man. That’s because of the way the “v” points downwards, highlighting pecs and stomach muscles that might not be as toned as they once were.
Excessive amounts of jewelry
Jewelery is another tricky one. Some men never wear it at all – wedding ring included. Others enjoy a signet ring, a bracelet, chain or all three. A good adage for the older man is “less is more”. It’s too easy to tip into the “bling” look, a problem that’s easily remedied by following Coco Chanel’s advice and removing one item before leaving the house.
A bare watch on a 50-something guy looks wrong. You might think it’s an attractive, casual, devil-may-care look but others are more likely to view you as an unreliable timekeeper who won’t turn up when he said he would. And, yes, it’s unfair if this isn’t true and you rely very successfully on your iPhone for timekeeping but sometimes life isn’t fair. Besides, any excuse to wear a nice watch is worth having!
Anything borrowed from your son
Your son might have the greatest closet in the world – or at least of anyone you know. However, borrowing an item from him is risky. Very risky. The other way round, of course, is fine, and almost to be expected. However, few teen or twenty-something boys want their father borrowing their clothes and doing so could risk a schism in your relationship. Plus, will they really fit – and will you honestly do them justice?
Fast fashion items
Although less-talked about in relation to men’s clothes, the problems surrounding fast fashion apply just as much as they do to womenswear. By your fifties, you’re definitely old enough to appreciate quality in clothing and also to understand the environmental implications of buying cheap clothing that frequently doesn’t last and quickly ends up in landfill.
Pajamas as daywear
Hopefully you don’t do this but, just in case, Pajamas or any sort of nightwear is only appropriate during daylight hours if you’re unwell enough to be bed-ridden. Younger guys – typically College-age – can get away with it, although it’s still not a good look but, by 50, there’s no excuse for not getting dressed.
“Going out” shirts
What do we mean by a “going out” shirt? First, it’s usually something with a collar (an idea for which we can probably “thank” golf clubs). Secondly, more often than not, it’s something that stands out in some way. It might be a garish pattern, a shiny fabric or even some funky buttons. Either way, it’s a cringey look that’s often sported by a man looking for someone to hook up with.
We appreciate that, just because you’re over 50, you won’t automatically be able to afford cashmere, merino or other luxury sweater fabrics. However, acrylic really is worth avoiding, especially if you’re reaching for the well-groomed look. If secondhand knitwear doesn’t grab you – and there’s plenty available and often of “as new” quality – why not look for seasonal discounts or special offers?
Ill-advised facial hair decisions is a risk at any age. However, the chin-strap beard, as popularised by Craig David in the early aughts is a real low-point. Don’t go there! Shaving a beard along the jawline can give even the most chiselled guy a double chin. On an older man, who may genuinely have the start of a double chin, the look is particularly unflattering. Tapering under the neck and avoiding harsh lines is much safer.
No matter how comfortable you find them or how cool you think they look, Uggs are an abomination on a man (and, frankly, usually on a woman too). You’ll quickly look both splay-footed and flat-footed – and desperately in need of some proper footwear. Hiking boots are your solution – and they’re usually also much cheaper.
While on the subject of footwear, let’s dispel the notion that square-toed shoes are a suitable choice for the over-50 man. They’re a clumpy, ugly design that even Gucci couldn’t manage to sell in sufficient numbers. A young guy will probably get away with them, although his girlfriend might raise her eyebrows. You, however, will look much more stylish in classic (and round-toed) Oxfords or Derbies.