David Beckham: The poster man for dressing well in your 40sInstagram/David Beckham
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How To Dress Well In Your 40s: Everything You Need To Know

Now that you're truly coming into your own, is your wardrobe keeping up?

By Palak Valecha | LAST UPDATED: NOV 19, 2025

Welcome to your 40s!

You'll complain every time you have to scan the menu at a restaurant, you'll start cracking 'dad jokes' (if you haven't already!), you'll get cranky if the TV volume is a little too high, and it'll take 2 business days for you to recover from a hangover, unlike your 20s when you used to be able to gulp down 5 beers without flinching.

But hey, with any luck, you are also probably at the peak of your success—doing well for yourself, having figured things out, built real friendships, and living a quality life.

How to dress well in your 40s: Tips and tricks you'll need

Having found success, it’s also time to dress the part. So we have put together some tips and tricks to help you dress impeccably as a man in his 40s.

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The Fit Makes The Fit

Typically, our bodies change as we age. Now that you’re in your 40s—maybe you’ve gained a few kilos, maybe you’ve lost some weight—you might want to get rid of items that might not fit you as well as they used to. Because nothing brings down an outfit like a bad fit. You might have the most impressive personal style, you might even be in great shape, but if your outfit doesn’t fit you well, you’re not going to look good.

Rami Malek
Rami Malek definitely knows a thing or more about the right fitInstgram/Ilariaurbinati

Serious Business

Dressing in your 40s should come with a little more gravitas. Wearing those oversized T-shirts, baggy cargos, neon clothes, Cuban chains, huge, in-your-face logos in your 40s won’t do you any favour—unless you are the first Punjabi singer to perform at Coachella and occasionally have arguments with Alexa—in which case, you will still look good wearing these and the rules don’t apply to you. But for the most part, your style in your 40s should be elegant and sophisticated. Crisp shirts, well-tailored suits, chic ties, exquisite timepieces, and immaculate shoes with not a hair out of place should be your jam. You should be dressing up even when you’re dressing down. For your off-duty style (assuming your professional role requires you to dress formally), you can have a little fun, but again, within the realms of classy—suede jacket, chinos, bomber jackets, cool sneakers. Those baggy ripped jeans can see themselves out in your 40s. Going too flashy or crazy in your 40s will make it look like you’re trying too hard to fit in with the younger lot, and not embracing your age. And that is not a good look on anyone.

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Standing The Test Of Time

By the time you reach your 40s, you should be way past trying every new fashion trend that emerges, only to realise that it doesn’t work for you. With any luck, you must know by now what works for you and what doesn’t. Don’t go around chasing every fad—leave the edgy stuff in your 30s. Invest in more classic, timeless pieces that work for you. And mind you, timeless doesn’t have to be boring—you don’t have to keep wearing the same black, grey and navy suits on repeat in the name of timeless. You can have a lot of fun with your outfits within the realms of timelessness—ties in interesting prints, two-tone brogues, houndstooth blazers, even casuals like bomber jackets, denim jackets, polo T-shirts. So timeless doesn’t mean dull, it merely means you don’t have to wear bootcut jeans just because Kendrick Lamar just wore it.

Adam Brody
Adam BrodyInstagram/Ilariaurbinati

You’re in your 40s—there’s a pretty good chance that your weight won’t fluctuate much either. So invest in pieces that will stand the test of time—in terms of both style and quality—and that you can wear even 15-20 years from now.

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The Devil Is In The Details

Maybe in your 20s and 30s, it is easier to get away with the devil-may-care attitude when it comes to style, but seasoned gentlemen pay attention to the details. You might be making a fashion faux pas (or many)—Are you not following the bottom button rule? Is your tie too long? Is your tie bar too long? Is your lapel too wide for your body type? Are you matching your tie to your pocket square? Are you wearing your tie with the top button of your shirt undone?—Maybe it’s fine for when you're pulling an all-nighter at work and going for the I’m-exhausted-look or you’re 3 hours into a party and you’re going for the danced-all-night-look, but not right away. We’re all for being rebellious when it comes to style, but these rules are rules for a reason. Fun fact: Many years ago, Anaita Shroff Adajania told Hritik Roshan that he wears his pants “too high and too tight”—and if the-literal-god-of-all-things-looking-good can make a fashion mistake like that, you’re not immune to it. Even the tiniest thing might be taking down your outfit by several notches.

John Krasinski
John KrasinskiInstagram/Ilariaurbinati

A Signature Everything

Presuming by now you know what works for you and what you like, you must have a signature everything. A signature haircut, a signature beard style, a signature perfume, signature eyeglasses and so on. Maybe there is a certain silhouette that you like wearing a lot because it compliments your body type. Maybe you like wearing navy blue suits often because it looks good with your eye colour. Maybe you like a certain kind of beard style because it shows off your jawline. Pick stuff that compliments your strengths and stick to them. Don’t change it every few years just because ‘you’re bored’. You’re beyond that now.

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Less Is More

When in your 40s, don’t buy as much as you would have in your 20s or 30s, but buy impeccable, quality stuff. You know the ‘16 piece rule’, wherein you can make a whole wardrobe with just 16 classic pieces—4 shirts, 4 pairs of pants, 4 blazers and 4 shoes? The different combination permutations of these items will give you 256 different outfits! Now you don’t actually have to follow the rule, but it just goes to prove that when you stick to the classics—which you should in your 40s—you won’t need a plethora of stuff to look stylish.

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menswear | mens style