40 Horrendous Style Mistakes Men Over 40 Can’t Stop Making

Turning 40 is no excuse to give up on dressing well.

40 Horrendous Style Mistakes Men Over 40 Can’t Stop Making
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“Dressing well is a form of good manners,” Tom Ford, the iconic designer—and the menswear world’s best-dressed man—once said. If his point is true (it is), then a lot of guys over 40 are in serious need of an etiquette lesson. Maintaining your appearance is a sign of respect—not just for yourself, but for all of the people you interact with on a daily basis. It shows that you care.

Let’s put it this way: you wouldn’t all of a sudden stop saying your “please“s and “thank you“s. You wouldn’t stop tipping your waiter or holding the door or even (occasionally) waving ahead the guy at the four-way intersection. So why would you stop dressing to the absolute best of your ability? After all, it’s just good manners.

1
Wearing Overly Baggy Clothing

“The number-one mistake I see men over 40 make is wearing clothes that don’t fit properly,” says Dave Bowden, founder of the men’s style site Irreverent Gent. Often, guys do this for one of two reasons: a desire to hide extra weight gained over the years, or a focus on comfort. But baggy clothing is mistaken solution to both problems, says Bowden.

For one, loose-fitting clothes will only accentuate body bulk, not hide it—he instead advises purchasing “clothes that hug your body, but don’t wrap you up so tightly you look like a sausage.” Secondly, comfort can be achieved far more easily (and fashionably) by choosing lightweight fabrics, like chambray or linen, rather than going for a draping fit, he explains.

2
Wearing Light-Wash Denim

dressing well in your 50s

“For some reason, once they hit 40, a lot of guys opt for the same light- or acid- wash jeans that were popular in the ’90s,” bemoans Bowden. While the look has been revived in certain corners of the fashion world, he explains that they’re more likely to make a man look like Tim Allen in Home Improvement. Instead, he recommends opting for a pair of slim-fitting dark blue jeans.

3
Dressing Overly Casual

man reading a book

“After a couple of decades of wearing a suit to the office, a lot of guys over 40 tend to go all the way to the other end of the spectrum on their downtime,” notes Bowden. This leads to situations in which their attire may leave you wondering whether they think they never left home. “By putting just a little conscious effort into their casual outfits, a lot of guys in their 40s could dramatically improve their off-hours look,” he says.

4
Buttoning The Bottom Button

single button suit

It technically functions as a workable button, but there are precisely zero circumstances in which you should ever cinch the bottom button of a suit jacket. Buttoning causes the tails of a jacket to flair out and brings the waist just a little bit too far in, all in all completely nullifying the streamlined silhouette of a good piece of tailoring. Oh, and it’s also a signal to everyone who knows the rule—in other words, everyone—that you don’t know how to dress yourself. Beware.

5
Sticking with That Same-Old Suit

Man Fidgeting with Suit Body Language That Kills First Impressions

“Yes, your lucky suit may have landed you the dream job 15 years ago, but a lot changes in 15 years,” says Amy Acton, founder of Acton Style Group. Not just what’s in style, but your body, too. “Odds are, it no longer fits quite the way it used to.” And when it comes to dress, “fit across the board is they key as you get older.”

6
Dressing Like a Frat Boy

snapback hat

“You’re a man—dress like a man!” says Acton. “That well-worn hoodie and backwards baseball cap are not the uniform of someone 40 and up.” She clarifies that the sweatshirt needn’t be trashed—but merely kept inside the house. As for the hat, “turn that around.”

7
Not Shopping Diversely

man shopping for shirts and suits in a clothing store

“It’s totally cool to hate shopping,” concedes Acton. “But be sure to think your purchases through instead of buying the same items over and over again.” While it may be easier to revert to default, you need a wardrobe that is complete. “If you closet is full of sweaters but you only have one pair of dress shoes, you might want to reassess your fashion needs,” she explains.

8
Stepping Out of the House in Ripped Jeans

ripped jeans are not appropriate for your 50s

“There’s a ‘destroyed’ denim trend right now, but frankly, it doesn’t apply to” says Joanna Lovering, founder of the style coaching service Copper + Rise. And she provides a helpful metric: “If your jeans are frayed on the cuffs, have holes anywhere, or show weather marks from your George Costanza wallet, you may only wear them around the house.”

9
Showing Too Much Chest

v-neck best tips for dressing well in your 40s

“We don’t need to know you’re a man from your chest hair!” says Lovering. “Ditch the low v-necks and only leave one or two, max, buttons unbuttoned at the top of an Oxford.”

10
Going Dull

“Just because you are getting older does not mean that you are boring,” warns Kimberly Monaghan, a personal stylist founder of The Wardrobe Refinery. Unfortunately, she sees far too many men shy away from colors and patterns as they get older. “You don’t have to wear all-over color or crazy patterns to make a big impact,” she says. But a nice pop of color worn underneath that suit jacket will go a long way.

11
Relying on Graphic Tees

graphic t-shirts

Too many men over 40 are of the mind that a prominent logo on their T-shirt makes it more respectable. New flash: it doesn’t. Stick with solids in tasteful colors. Or, if you must rock a logo, choose one that’s both subtle and fashion-forward.

12
Mismatching Belts And Shoes

best dressing tips for 40s

One of the very first style rules a guy learns is simple: Make sure your belt and shoes match—or, at the very least, never, ever pair black and brown. Unfortunately, it’s also one of the first rules that fall by the wayside. Don’t let that happen!

13
Putting Sandals Over Socks

style tips

Many men seem to be under the impression that, once they hit 40, wearing socks underneath sandals is a reasonable option. Heads up: This makes zero sense. Not only does it look lazy and unkempt, it’s also woefully uncomfortable. Just get some sneakers. Or better yet, go sock-free. It’s a subtle move that will instantly boost your sex appeal.

14
Layering Collars

Steve Bannon wears two collared shirts

Come on, guys. A collar is meant to frame your face, not create an optical illusion.

15
Owning White Socks

white socks and dress pants are something no man should wear to work

White socks belong in two places: At the gym, and on Michael Jackson’s feet. Full stop.

16
Trying Pleated Pants

Some guys are glad they died in the ’90s. Some are guys are still wearing their pairs from the ’90s. But no matter how you feel, pleated pants are coming back with a vengeance. Thing is, it’s really the fashion set (read: whip-thin guys between 18 and 24 years old) that can rock the look. Wear pleated pants after 40 and you’ll look like you’re trying too hard to relive your youth.

17
Getting Too Matchy-Matchy

man wearing a denim jacket and jeans

It’s a perfectly natural thought: It it matches, it works. But leaning too hard into the whole same-same aesthetic—a blue shirt with navy pants, a black shirt with a black blazer, or the cardinal sin of menswear, the Canadian tuxedo—is only going to make you look uninspired and uncreative. Spruce things up with some contrast.

18
“Athleisure”

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“Now that athleisure has muscled its way into the culture, a lot of men over 40 seem to think that wearing sweat-wicking athletic gear in non-athletic situations will make them look younger, fitter or more athletic,” says Bowden. “Unfortunately, in most cases it just makes them look much like the guys wearing hoodies and sweatshirts everywhere: under-dressed, out of place, and easy to overlook,” he says.

19
Untucking Traditional Dress Shirts

man wearing an untucked gingham dress shirt

Traditional dress shirts are meant to be tucked in; that’s why they’re so long in the back and front. Untucking a dress shirt won’t give you the laissez-faire vibe you think it will. You’ll just look messy. If you’re looking for a shirt you can wear off-duty, look for something with shorter hems, a trimmer fit, and trendy fabrics—something like The 10 Best Button-Down Shirts You Need to Wear Untucked.

20
Leaving a Visible Undershirt Collar

white tee shirt Never Buy

For both comfort and the purpose of wicking away sweat, many men choose to wear undershirts underneath their dress shirts. Fine. But an unfortunate side effect is that far too many allow the collar of the undershirt to peak out above the collar of the dress shirt. This sort of style can be best described as sloppy and uncouth—not what you’re looking for.

21
Wearing Ties That Are Too Long

man retying a striped tie

Your tie should stop right at the top of your belt. No higher—and definitely no lower!

22
Showing Too Much Sleeve

french cuff white shirt sleeves on a suit jacket

Same thing here. If you’re wearing a suit jacket, you should only show 1/4″ of sleeve. No more—and certainly no less!

23
Stowing Away Bulging Phones And Wallets

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Whether because they’re actually busy and important—or merely trying to come off as such—many men over 40 walk around with phones, wallets, or other personal items bulging from their pockets. While this might be a utility-maximizing arrangement, it makes them look as if they suffer from rectangular growths on their thighs and chests. Needless to say, it isn’t a pleasant sight.

24
Wearing Bowling Shirts Away From the Bowling Alley

If you’re wearing a golf shirt away from the golf course, you’re doing it wrong. If you’re wearing a bathing suit away from the swimming pool, you’re doing it wrong. If you’re wearing a bowling shirt away from the bowling alley, like Ryan Gosling here, you’re… Well, you get the point.

25
Popping Their Collars

no man should wear a popped collar at work

While the younger cohort has largely learned their lesson when it comes to popped collars (mainly: don’t), it seems like many men over 40 haven’t gotten the memo. In addition to laws of gravity, this move violates a whole bunch of laws of style, too.

26
Wearing a Vest and a Tie Bar

tie clip guy

A vest keeps your tie close to your shirt with minimal frump. A tie bar does the same. It’s a redundant move—and also aesthetically just too much for the eyes. Pick one or the other.

27
Going with a Skinny Tie

guy wearing a skinny tie and a peak lapel jacket

Only two types of guys can pull off the skinny tie: British rockstars and male models. You could be the handsomest guy in town, and sheer statistics would suggest you don’t fall into either category. So follow this rule: Your tie and your jacket lapels should be roughly the same width. At most, you can get away with your tie being about half-an-inch thinner than the lapels.

28
Going with a Power Tie

man wearing a tan suit and a purple tie

Reference the rule for skinny ties. Same goes for fat ties. And if you’re going with the power-tie look—shiny and ostentatious, like you’re a side character from American Psycho—you’re trying too hard to be masculine.

29
Sporting Athletic Watches Outside the Gym

man with plastic watch

A plastic watch is appropriate in the gym, shower, and if you take to the seas. Otherwise, if it comes with assurances that it’s sweat-proof, it’s not meant for the out-and-about.

30
Wearing Socks That are Too Short

socks on a heater next to books and a cup of tea in a home in winter

Far too many men are under the impression that when it comes to socks, anything goes. But if your leg hair peeks out every time you cross your legs, you’re in need of a few extra inches of fabric.

31
Applying Too Much Cologne

cologne grooming Things You Should Always Do at a Fancy Restaurant

A gentle reminder to the men out there: a scent’s effectiveness is not positively correlated with its prevalence. In fact, the opposite is the case. So next time you spray, ease up on the index finger. Two spritzes on the wrists, one across the chest. And if you’re looking for a new scent, check out these 15 Must-Have New Men’s Colognes.

32
Owning Square-Toed Shoes

style tips

It’s common knowledge at this point that you should refrain from any footwear that turns your toes into rectangles. However, a bunch men seem to have missed the memo. As for the department stores that take advantage of their ignorance to offload product: shame on you! For better footwear options, check out these 8 Amazing Monk-Straps For a More Stylish Look.

33
Wearing Scuffed Shoes

tailor secrets

It’s not just the shape of your shoes that matter, but the condition, too. Yet as if there were an effort to drive shoe-shines out of business, far too many men walk around with scuffed footwear. More than edgy, however, it makes them look childish—as if they never learned how to take care of themselves or their leather.

34
Attempting Ugly Sweaters

man wearing a santa hat and a christmas sweater

For younger people, ugly sweaters come across as ironic—because they’re making fun of the outfits of the over-40 set. A guy over 40 wearing the look isn’t ironic. It only gives the 20-somethings ammunition.

35
Leaving Blazers Buttoned When Sitting

man sitting and wearing a buttoned suit

Talk show hosts and news anchors can get away with sitting down and buttoning up their suit jackets. Everyone else? All they’re doing is needlessly stretching the threads of a perfectly fine jacket. Just unbutton, man!

36
Skipping Tailoring

dressing well 50s

Pants that break over the laces. Shirts that billow like sails. Suit sleeves that fall past the wrist. Refusing to get your stuff tailored is like buying a Maserati…and then neglecting to soup it up with an F136 engine. (That’s car-speak for “a really good engine designed by Ferrari that’s available on certain high-end Maserati models.”)

37
Pairing Black with Brown

man wearing plaid blazer black pants and brown shoes

Pulling this look off requires a level of sartorial jujitsu few men have ever attained. (Kit Harington successfully did it—but only once. And he’s King in the North, so he can get away with pretty much anything in the style department.)

38
Wearing Square Shouldered-Blazers

best tips for dressing well in your 40s

At one point in time, sharp, rectangular shoulders were the big thing in men’s fashion. Fortunately, we’ve all come to our senses. If you’ve got any of these boxy relics left in your closet, get rid of them, stat.

39
Matching Shirt and Tie Color

man wearing light blue shirt and light blue tie

A tie is meant to create visual depth and elongate the torso. But wearing a tie that’s too similar in color to your shirt does neither. Plus: neckwear is an opportunity to add some fun contrast to a look. Why pass that up?

40
Refusing to Let Go of Cargo Shorts

dressing well in your 40s

You should really know better by now. And for more great fashion advice, learn all about the 40 Best Style Brands for Men Over 40.

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