Casual Dressing for the Man in His 40s

Your forties are when you start to carry yourself with some serious authority.

These days, it’s also not the fixed quantity that it used to be. Men in their 40s are often just as dynamic and adventurous as they were in their 20s and 30s, if not more so. You don’t have to dress like someone who’s settled into his job and is just waiting for retirement.

With a little luck, you’ve also got a bit more money to spend in your 40s than you did when you were younger. If you don’t, don’t worry about it — you can still look good. But if you do have an enjoyable disposable income, don’t be shy about making some serious investments in your 40s.

Casual in Your 40s: Needs and Wants

At any age, your “casual” wardrobe is essentially your non-business wardrobe. It can even include some clothes that you do, in fact, go to work or do business in, just worn in ways that set them apart from your office outfits.

What it isn’t, and what it especially shouldn’t be at this age, is sloppy. A man in his forties can do better than sweatshirts, and if he’s wearing ripped jeans, he’d better be in a band. And on-stage.

How you dress when no one’s requiring you to look any way in particular says a lot about you. As you enter (and, for that matter, exit) your forties, here are a few things you want to be thinking about:

1. Fit

This is the most important consideration for a man of any age, but it takes on special import as you age.

Bodies change. Sometimes they change for the better, and sometimes not, but it doesn’t actually matter much as long as you stay on top of it. A middle-aged man in a custom-tailored jacket that slims his silhouette down and squares his shoulders for him? Smashing. The same man in a jacket that pinches at the shoulders and sags at the waist, not so ideal.

Your body type doesn’t matter. Getting the right fit for it does. And at your age, it’s time to have the simple task of getting your clothes fitted down to practiced routine: find a tailor you like, get him your measurements, and take everything you buy to him for fitting.

Yes, everything. All right, maybe not the socks and underwear, but anything other people are going to see. Trousers, shirts, jackets, overcoats — if you’re going to be wearing it stylishly, get it adjusted. It’s the cheapest way to look good that there is.

If you can afford it, take your best wardrobe pieces a step further by having them tailor-made from scratch. A good made-to-measure suit stands head and shoulders above even a well-adjusted one off the rack, and true bespoke — while pricy — puts you in a whole different class from other men.

2. Dignity

Over forty is the time to start wearing your silver hairs with pride (even if you don’t actually have any silver hairs yet). You’ve got the years to carry yourself with a little gravitas. Start doing it.

That doesn’t mean double-breasted suits at all times, of course. But it does make darker colors, richer cloths, and sturdier cuts a good idea — a little more of the esquire, and a little less of the dandy.

Be willing to expend the little extra bit of time, money, or effort that you didn’t in your younger years to get things just right. Get your shirts pressed more often. Perfect a fancy, three-pointed pocket square fold. Wear a scarf that highlights your eyes. It’s all about the little things at this point.

It goes without saying that this is also a good time to be leaving behind the edgier fashions, even ones that you’ve pulled off in the past. A savvy dresser probably can still wear red Converse sneakers with a suit jacket in his forties — but he doesn’t need to, and he’d be better-served by something more restrained.

Don’t mourn the flashy fashions. Exceed them.

3. Investment

You’re hopefully reaching a time of life when your body won’t be doing too much more changing in shape or size. You might put on or lose a little weight as you age, and we’re all going to shrink at least a bit, but for the most part you can hope that clothes you buy in your 40s will still fit in your 60s.

That means that it’s time to start investing in some pieces with serious lifespans. Buy less frequently but more exclusively than you did in your 20s and 30s, so that you’re creating a small core of top-quality garments to go with your general staples and older remnants.

There’s no real rule or order for what to buy first, or what to stock up on. Let your pleasures be your guide here. Just buy with an eye toward the long haul. You’ve got to be optimistic, right?

Casual Looks for Your 40s

Hopefully you’ve already got a good sense of the sort of look you like — rugged or crisp, classic or modern, all of that. If you don’t know your look, now’s the time to figure it out. Take a turn through some of the nicer menswear stores in town and see what styles you enjoy trying on, then build from there.

But for the most part a man in his 40s can be counted on to own a decent collection of clothes he likes already. Now’s the time to start finding ways to improve it: make things a little dressier, a little more luxurious; a little more more.

These are a few looks that the 40-something man should feel comfortable wearing, and merit space in his wardrobe:

1. The Serious Business Suit

We usually recommend that a man get a proper business suit as soon as he’s out of college, or even before then if he’s in a field like finance or law. That’s a basic wardrobe necessity.

But a middle-aged man is at the right stage of life to upgrade from a business suit to a serious business suit. This should be something with real heft to it — thick, luxurious wool that no one’s going to mistake for the $299 special at Men’s Wearhouse.

Go ahead and get it in something beyond the basic two-button, notch-lapel jacket style. Peaked lapels? Sure. Double breasted? Go for it. Pin stripes on that dark, rich color? Keep ’em modest — true pinstripes, just a needle’s width of white color — but why not? Do something to shake the generic formula up.

This will, of course, become one of your business suits. You’ll wear it when you need, well, a suit. But it’s something that can make the occasional “casual” appearance as well, at evenings at the theater or Sunday morning services, to say nothing of any upscale events like country club dinners you might find yourself invited to.

It’s not a cheap piece and it’s not an everyday piece. But it is a piece worth owning, and one that announces you as a man of stature.

2. The Perfect Blazer

Middle-aged men look good in the square, firmly-constructed silhouette of a classic blazer. It’s well-suited to their stage in life: solid, dependable, and comfortable.

You should own a good blazer. Ideally you should own several, but have one that’s your favorite, and perfect for you.

It doesn’t have to be the traditional navy blue with brass buttons, though that’s a good look. Other dark colors work well and stand out a bit more. For buttons, anything from a basic matched color to wooden or leather toggles works. If you’re feeling extravagant, personalize with monogrammed metal buttons.

You can wear a blazer with almost anything — that’s one of the reasons to own a good one. Pair it with gray slacks and a necktie when you want to impress, or with jeans for a lazy weekend afternoon. Khakis will do for just about anything in between.

Mix it, match it; own it. These are your best blazer years.

3. The Casual Coat

As great as they look, suits and blazers aren’t the only kinds of jacket a man should own.

One of the marks of a well-dressed man is his outerwear’s ability to stand with the rest of his outfit. As part of your long-term collection, lay in a few coats that you can dress up or down as needed.

A long, straight, wool overcoat is a good staple, and a good starting place. Once you own one of those in dark wool, add another in a lighter color and a different cut, or switch to a shorter style like a peacoat.

A man in his forties can certainly wear a leather coat as well, but it should look a bit like him: sturdy, weathered, and starting to show a few lines here and there. Leave the shiny, sleek motorcycle jackets to guys with something to prove. Yours should be simple, a little worn, and very expensive.

Three Items Every Man in His 40s Should Own

1. A Really Nice Hat

Don’t let us limit you here — you can own several really nice hats if you want. But you should own at least one handsome, shaped felt hat from a classic style: homburgs, fedoras, derbies, western, etc.

A softer wool cap like a newsboy’s or fisherman’s isn’t a terrible idea either. In fact, if you’re putting a coat on over your outfit, you should pretty much always be planning on having something on your head as well.

2. Well-Fitted Leather Gloves

This is another of those little things that sets men with really complete wardrobes apart from the men who are still phoning part of it in. Get a pair of good leather gloves that fit your hands well: close but not so tight the leather discolors when you close your fist, and long enough to tuck into your coat sleeves.

Black and brown are the obvious choices here, but colorful leather gloves have a long and masculine tradition. Feel free to experiment. Just keep it relatively dark and subdued — oxblood red rather than bright cherry, hunter green rather than lime, and so on.

3. A French-Cuff Shirt (and Cufflinks)

In theory, French cuffed shirts are exactly the same as any other dress shirt. You wear them the same way; one style just requires cufflinks.

In practice, you won’t see French cuffed shirts being worn without a jacket much. That’s not to say youcan’t do it, but it’s best suited to wear with a nice blazer or a suit.

And you should be wearing one once in a while. Get good cufflinks to go with it. Nothing too flashy, and nothing novelty — you can wear Playboy bunny cufflinks if and only if you’re Hugh Hefner, and brother, you ain’t.

Looks for the 40-Something Man to Absolutely Avoid

There’s no “but maybe” on these. They’re things you shouldn’t be seen wearing in public. So don’t be.

•      Anything elastic-waisted. Sweatpants, stretch jeans, pajamajeanjeggings or whatever they think of next — don’t do it. If you find belted waists too constricting, wear slacks with suspenders (braces for our UK readers) instead. They’re a timeless, classic style that looks just fine on a man in his 40s — unlike stretch waists.
•      Ascots. Yes, some designers are starting to play around with them again. Yes, younger men have started wearing brightly-colored one. No, you’re not going to do that. If you’re wearing daytime formalwear and you actually know what you’re doing, you can tie yourself an ascot-style cravat, but leave the neckerchief-looking ones to younger fashionplates.
•      Unfinished trousers or jackets. When you buy ready-to-wear (off-the-rack), take it to a tailor and get the hems and sleeves finished. A man in his 20s can get away with loose, unhemmed trouser bottoms (not that he should), but at your age there’s really no excuse.

You can deal yourself in on the standard prohibitions for every well-dressed man as well: no gym clothes unless you’re actually at the gym or doing yardwork or the like, no sports jerseys unless you’re actively watching that team play; no rubber watches or sneakers except on an athletic court.

Other than that, let your own taste and the people you’re interacting with be your guide. If you mostly hang out with guys that like to drink in sports bars and go hunting, you’re probably not going to need a structured blazer and wool slacks every day.

One final note: not all men in their forties have families or children to think about. But if you are a father (and whether your children are boys, girls, or not even completely decided on that yet), there’s extra incentive to dress both well and comfortably. It may not seem like it, but your kids will notice when you’re the best-dressed dad in the room — and when you’re the worst-dressed.

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