How to Dress Your Age for Men (40s, 50s) in 2023

They believe life begins at 40, which, to be honest, is a little too Benjamin Button for comfort. It’s also obviously false. Even if you may realistically expect to live to reach 80, up from a short and not particularly sweet 25 in medieval times, your fifth decade is at best middle age; you’re cresting the hill, if not already over it. Salad days are now only available if you follow the 5:2 diet.

But that means it’s all downhill from here – in a good manner. You’ve made a name for yourself and your particular style. You don’t have to wear what’s in style. Even if you’re at your top earning potential, you don’t really need to buy anything, so you may afford frivolities like bespoke suits and high-end watches – especially if you’re no longer paying through the nose for full-time daycare.

Life may not begin at 40, but your style does not have to finish there either. So, if you have any uncertainties, trust Teeanime.

HOW SHOULD A 40 YEAR OLD MAN DRESS: TOP STYLE TIPS

DON’T RETIRE TOO EARLY

“I’ve always felt that if you have confidence, you can wear anything,” says Olie Arnold, style director of Mr Porter. “However, by the age of 40, you should have a decent notion of which fits and styles suit your body shape. Otherwise, tailoring is always an attractive and age-appropriate alternative.”

“Experiment with pleated and carrot-top pants, or different fabrications and textures in knitwear and jackets,” she says.

SEPARATE YOURSELF FROM THE HERD

If you play it too safe at work, you’ll become just another drone in a ten-a-penny two-piece. “In a sea of ill-fitting tailoring, a well-fitted suit will look understatedly attractive,” Arnold says. “Unstructured separates, on the other hand, can create a more casual style, whether worn together or dressed down with knitwear and a grandad-collar shirt.”

Browse Italian labels such as Boglioli before lacing up your John Lobbs – or throwing on some slick shoes.

BUILD A SOLID OFF-DUTY FOUNDATION

When you’re not at work, the worry is that you’ll fall into dadwear – and not the sardonic, stylish sort. “Teaming tailoring components like an unstructured blazer with chinos or jeans keeps a slight edge, and you can keep it casual with a T-shirt,” says Arnold, who also recommends cargo trousers as a contemporary alternative to denim: “They’ll nail a casual yet polished weekend look with a suede bomber, sweatshirt, and sneakers.” Not at all.

CONTAIN MIDDLE-AGED SPREAD

Fit is one of the main differences between stylish, undistinguished, and plain slobbish. Cargos, properly condemned in their huge, Fred Durst-endorsed version, are okay if they’re the right size. That applies to your body and anything you cover it with. Trimming helps. A lot.

WORSHIP THE DETAIL DEVIL

When the rest of your equipment is deliberately understated, accessories truly shine. Arnold suggests incorporating color, pattern, and texture into your accessories. Consider patterned silk scarves or knitted ties. Other finishing touches, such as leather gloves and matching luggage, help, but the main attraction is a luxury watch.

“You’ve worked hard for 20 years – you deserve it,” Arnold, a fan of Piaget and IWC Schaffhausen, remarks.

BE WARY OF SPORTSWEAR

“I don’t believe there are any specific limits,” Arnold says of continuing to play in athletic-inspired gear into your fifties. However, hoodies, backpacks, and baseball caps have an undeniable youthfulness that may clash with your veteran status.

If you’re wearing sweatpants or joggers, they should be high-quality, plain versions made of a different fabric than jersey; your trainers should be simple. However, like with most sports, fitness is crucial to success.

GROW OLD GRACEFULLY

Don’t let yourself be seduced to colour your hair. Yes, it may appear faintly plausible today, but you’ll be locked in a cycle of constant, costly upkeep until it fools no one except yourself.

Then you have the option of dyeing it greyer or pretending to have endured a horrific trauma and turned white overnight. Reach for the clippers if you’re balding. And any mention of botox or facelifts will raise an eyebrow.

KEY PIECES TO BUY IN YOUR 40S

A BESPOKE SUIT

After building your tailoring wardrobe in your twenties and upgrading it in your thirties, you’ve reached the age, earning bracket, and body shape to commission. A tailored suit should last at least 20 years if properly cared for (brush frequently, dry clean infrequently), so while it’s an investment, it should last you through to retirement.

NEAT KNITS

While cardigans’ grandpa connotations are exaggerated, knitwear looks more grown-up (and smart-casual) with jeans and a T-shirt than a sweatshirt or hoodie. And if your children have ceased vomiting and defecating randomly by now, you might consider treating yourself to some cashmere.

SWAG BAGS

If you’ve already realized the need of a holdall for weekday gym excursions and weekend city breaks, make sure the rest of your luggage is equally beautiful and coordinated: a long-haul suitcase, a cabin-sized wheelie case for short flights, and possibly a carry-on tote or suit bag. The earth does not help real men carry their luggage, but wise, old men with bad backs do.

AN HEIRLOOM WATCH

Maybe you didn’t get to mechanical in your thirties, or maybe you only got to entry level. In any case, your forties are the time to plunder your children’s college funds for some serious wrist candy. (After all, the money isn’t earning any interest, and a Rolex or Patek might even appreciate.)

Tell the kids you’ll pass it on when they graduate – or when you die.

AN AIR OF MATURITY

Fragrances, like clothing, can be age (in)appropriate. Whereas new releases tend to follow a generic citrus-wood-amber template and smell like a replicant’s hairpiece, sophisticated perfumes will frequently have an appropriately old sense, if not an issue date that precedes yours. And a trace of leatheriness on your skin isn’t a negative thing in this case.

40 YEAR OLD MEN STYLE ICONS

DAVID BECKHAM

David Beckham’s style, albeit more suited and less booted since his retirement from football, continues to defy the norm of not wearing athletics (or even streetwear) into your fifth decade. However, the fact that the lanky 42-year-old looks like he could still play right wing buys him some time. If you can’t compete, don’t bend it.

COMMON

The hip-hop musician is distinguished by pristine, slightly preppy tailoring and a youthful attitude to streetwear. One of the main reasons the 45-year-old gets away with it is his meticulous attention to grooming. Common, like Beckham, recognizes that beautiful skin – and hair care – is a free pass to wearing fashions that most guys in their 40s believe they’ve outgrown.

PEP GUARDIOLA

With his unique touchline apparel and tactical ideas, “Don Perfecto,” as the Manchester City manager was dubbed at Barcelona’s academy, takes as much care with his costumes as his line-ups. Although, when wearing a suit, he should remove the belt, especially if it’s so tight.

PATRICK GRANT

To be sure, it’s easy to appear dashing all the time when you’re the owner of Savile Row tailor Norton & Sons and the creative director of catwalk brand E. Tautz. Aside from his arsenal of blue and grey tailoring that would make any Kingsman jealous, “P Greezy” is a testament to the power of a good, regular haircut and beard trim. The man, too, enjoys a wide-leg trouser.

RYAN REYNOLDS

Van Wilder has grown a lot since his days as a party liaison. His collection of traditional pieces in muted color schemes includes everything from red carpet-ready three-piece suits to an olive overshirt and khakis. Everything fits his gym-honed Deadpool-bod like a tailored glove, so the father of two never appears like a deadbeat parent, whether he’s flexing in a tux or relaxing in a tee.

STYLE CHECKLIST: WHAT TO CROSS OFF BY 50

TURN TO THE DARKER SIDE

As you age, your skin becomes lighter and thinner, so brights, pastels, and some neutrals may wash you out. That doesn’t mean you have to wear only blue and grey (too much too-dark might do the same thing), but rather warmer tones like sand or camel rather than beige or stone.

STAY ON COURSE

Middle age can have odd effects on a man’s mentality. Trying to be too daring in your older years, on the other hand, is more unfortunate than Indiana Jones And The Kingdom Of The Crystal Skull. That leather biker jacket is a bad choice for a false grail. That hog.stone is the same.

BE A RIGHT OLD SEW AND SEW

It does not contact the skin if it has not been adjusted. You should have known your tailor longer than some of your pals. And you should see your barber more frequently than most – every four weeks. A well-manicured coiffure will erase years – and pounds.

CLEAN OUT YOUR CLOSET

The only aspect of your outfit that should look like Eminem’s is the inside. T-shirts with slogans or logos, excessively ripped or distressed denim, hype trainers, ironic timepieces, and narrow tailoring are all things to avoid. Donate them to a local charity shop. Or even your 12-year-old kid.

RENEW YOUR GYM MEMBERSHIP

Ryan Reynolds is 40 years old. Jason Statham is 50 years old. Both of them have recently graced the cover of Men’s Health. For reps, the bar for what a middle-aged man looks like and is capable of is being lifted. You’re only as old as the Hollywood actor with whom you work out.