in: Featured, Outfit Guide, Style

• Last updated: September 25, 2021

A Man’s Guide to Dressing Sharp and Casual in His 50s

Vintage man in his 50s wearing blazer and aviator sunglasses.

A man’s wardrobe should undergo subtle shifts as he gets older and takes on different roles in life. To help you look great at every age, this year we’ll be offering guides to dressing sharp and casual in your 20s, 30s, 40s, 50s, 60s, and beyond.

There’s a joke that “we spend all our lives trying to look older, right up until we spend all our lives trying to look younger.”

Terrible idea, really. The perfect age to be is always the one you are (though we have to admit that being of legal age to do everything is always an improvement). Your 50s are no exception to the rule.

This is the decade when a man should fully come into his own. You’re a gentleman with a firm idea of himself and his place in the world, and your wardrobe should reflect that.

Casual in Your 50s: Needs and Wants

Your business wardrobe is your business wardrobe. It’s dictated by the necessity of your profession. Do it well — but do your “casual” wardrobe better.

Your casual clothes are, quite simply, what you wear for yourself. It’s the most obvious outward expression of your taste, your attitude, and your place in life.

Confusing “casual” with “sloppy” is the bane of men everywhere, and of all ages. Just because you’re not at the office is no reason to look like you don’t care. Your clothes should still look like a deliberate choice and a conscious statement — a powerful one, too, at this age.

Here are the top three things a man in his fifties wants to keep in mind when choosing his casual wardrobe:

1. Fit

By this decade of your life, you should have a very good sense of your body — and a good tailor who can make adjustments to suit it.

The guy (or gal) you go to doesn’t have to be someone who actually creates tailor-made clothing, though they’re often the best. There are perfectly good tailors at basic clothing repair shops and even some dry cleaners that can do adjustments. The point is that you should be getting those adjustments done.

Get everything trimmed to fit you. Suits and jackets go without saying, but get your trousers and your shirts nipped and tucked too, even the more casual ones. About the only thing you should be leaving unadjusted at this age are your socks, underwear, and gym/chore clothing. Everything else gets a tailored fit.

This has a twofold benefit: it makes your body look better, flattering the best parts of your figure, and it also makes you more comfortable. A big part of looking good in your 50s is looking relaxed and at ease with yourself — hard to pull off when you’re constantly re-tucking your shirt or tugging the crotch of your pants into place.

2. Comfort

On that note, a man in his fifties really should look comfortable, and even relaxed, at nearly all times. Leave the hard-edged, high-strung look to younger guys.

A lot of looking comfortable in your clothes comes down to actually being comfortable in your clothes (see #1 just above), but you can do a lot with tailoring and styling too.

This is a good time of life to be moving away from aggressively fitted “power suits” and sharp-edged European cuts. The American, slightly looser suit was made with the middle-aged man in mind — give it a try.

For less dressy styles (i.e., not suits), try relaxed looks like sweaters and turtleneck/rollneck shirts that move you away from the business-standard dress shirt and its turndown collar. Handsome, well-fitted clothing that’s obviously made for leisure tells people that you’re prioritizing your own pleasures.

The key here is to have stylish comfortable options. Yeah, stretch-waist sweatpants are comfortable, but there’s such a thing as too much of a good thing. Buy dressy, grown-up clothes, just buy them in soft fabrics, relaxed cuts, and a nice casual variety of colors.

3. Luxury

Not to be confused with comfort, though it often provides it, luxury in clothing is the province of the older gentleman.

This mostly comes about as increased discretionary income intersects with a life’s worth of dressing experience. Even if you never got that serious about your wardrobe, 50+ years of putting fabric on your body gives you some idea of what feels good and what feels cheap.

Rich wools, soft cottons, light linens — live ’em all up. The texture and “drape” of a good fabric are more noticeable, even at a distance, than we often think. It’s the reason a bunch of men in $99 blazers from the sale rack at Men’s Wearhouse all look vaguely insubstantial — and the reason a man in the middle of them wearing a $599 blazer made from top-notch worsted wool stands out like a lighthouse.

Buy less frequently than you did when you were younger, but more expensively. Decades of accumulation should have your wardrobe in decent shape for the staples. That frees up your clothing budget to add a couple really nice things for yourself.

Whatever you like to wear most, buy it in the best quality you can get. Then wear the hell out of it.

Casual Looks for Your 50s

When you were younger, your style perhaps could have been summed up in one or two words: “urban cowboy,” “power exec,” “thrift-store hipster,” whatever.

By now you should be past that. Your clothing should just be you, defying categories. It should look like what you wanted to wear, not like what a style blog told you to wear.

Maybe the most important thing at this age is for everything to look like an outfit, rather than a collection of unrelated clothes all thrown on together. You should put some time and care into selecting not just the big pieces (trousers, shirt, jacket), but the accents as well (everything from the necktie and shoes to things like scarves, watches, hats, pocket squares; even your eyeglasses if you wear them).

With that in mind, here are a couple of looks that will always look good on a man in his 50s:

1. The Sunday Best

We’ll start at the top end of your casual wardrobe: the social suit and tie.

For most men, especially younger men, this doesn’t exist anymore. Suits are strictly business wear, and not even then are they a necessity for a lot of professions.

That just makes it even easier for you to stand apart from the crowd when you dapper it up. A suit in a casual color and pattern offers all the things we talked about above: luxury, comfort, and, if your tailor did his job right, a perfect fit as well.

The traditional time for a man to wear his social suit was on Sunday, to church and then to the inevitable social activities afterward, but don’t let that middle-American habit limit you. A casual suit, with or without a necktie, is always good daytime wear when you want to look sharp.

After 5:00 or so be sure to skip the necktie — you don’t want to be mistaken for a businessman with dubious professionalism coming home from work. Leave the collar open unless you’re going somewhere very fancy (and if you are, maybe wear a darker, more somber suit).

2. The Stroller

A “stroller” is an older phrase for daytime semi-formalwear, especially for being out and about — truly strolling somewhere. You should own a good walking outfit, or several, because frankly a man in his fifties needs to be walking from time to time. It keeps you in good shape — and strolling down Main Street, taking in the crowd for no reason other than personal pleasure is both a perk and a tradition of the silver-haired years.

So own some simple, comfortable wool trousers and a couple of casual long-sleeved shirts. Throw a tweedy sports jacket or a sweater over them and put on some leather work shoes (rubber-soled, but beware of clunky orthopedics — if possible, go with inserts to provide support, rather than built-up soles). Suddenly you’re a respectable gentleman of means out for a stroll.

A couple of good accents help with this one. Own some scarves, hats, and gloves with a little flavor to them. Yes, you could wear a baseball cap and stick your hands in your pockets, but you can do better than that.

3. The Silverback Badass

Style in your fifties is all about not trying too hard. You don’t want to look like a rebel without a cause. That was silly when you were 20, and now it’s really silly.

But can you still be a bit of a rebel from time to time? Sure. A man in his fifties can still wear a leather jacket and jeans, or a denim coat and cords. He just has to make it a little more dignified.

This is a great age for plain-fronted leather jackets — think stripped-down bomber or fatigue styles, not too heavy on the details and fitted close but not hyper-streamlined (read up on wearing a leather jacket with style). Don’t be shy of a little surface weathering; it goes well with gray hairs (assuming you have those — some guys don’t, even in their fifties).

If leather’s not your thing, show some attitude with mix-and-match levels of formality instead. Wear a plush velvet suit jacket over a pair of jeans and let people like it or lump it. You do what you want, right?

It’s important not to get too experimental — you don’t want to look like a runway designer’s latest vision. That’s for younger men. If you can’t wear the look with casual confidence, skip it. But if you can, go ahead and be a rebel now and again.

Three Wardrobe Items (and One Product) Every Man in His 50s Should Own

1. A Wool Cardigan

No, it’s not a grandpa sweater.

Did Steve McQueen wear grandpa sweaters? No. He wore cardigans, and he looked rugged as hell doing it. So did John Wayne. So does Daniel Craig. They’re awesome, and you should have one.

A good cardigan should be knit wool, heavy enough to be your outer layer for much of the fall and spring. An inner lining of something like flannel makes it warmer and can minimize dry cleaning needs as well. Stay away from hugely oversized floppy collars or really big buttons — those are a little feminine — but otherwise feel free to play around with styles.

Gray is always a reliable color if you don’t feel like experimenting. For the more adventurous man in his fifties, try a cardigan in deep shades of bright primary and secondary colors — burgundy red, forest green, burnt goldenrod.

You can throw a good cardigan over almost anything and be ready for everything from brunch to a cozy late night coffee date. Expect to, once you’ve bought one you like.

2. A Good Scarf Collection

Scarves as a style piece rather than a functional necessity are a direct descendent of early airmen and fighter pilots. That made them popular during the interwar years in America, and worn well they still lend you a little of that old-fashioned, dashing appeal, like a gentleman who goes about in something called a “motorcar.”

Start with the basics (black and brown) and then start adding color and pattern. A scarf can be an eye-popping centerpiece or it can blend right into your jacket until the moment when the wind catches the end and whisks it about. Both are good.

While you’re at it, practice a few different ways of looping/tying your scarf. There’s no reason to use the same knot every time. Thin materials look better in different knots than thick materials, and you may want a more or less structured look depending on the rest of your outfit.

So are you fully scarf literate yet? If not, that’s a good project for your fifties.

3. Suede Shoes or Boots

You’re done with sneakers and court shoes at this point in life, except for on the actual court. Suede is your new casual, comfortable footwear default.

For the classically-styled man, bluchers in white, gray, blue, and brown are the way to go. If your style is more modern (and you find yourself missing canvas or rubber sneakers), suede skate-style shoes with contrast lacing make a nice grown-up alternative to teenager’s footgear.

And if you’ve never tried the look, go ahead and get yourself a pair of high-ankled boots in suede. They’ll serve you from about the time it gets too cold for sandals to when the snow starts falling, and the reverse in the spring.

4. Skin Care Lotion That You Respect

Ignore the commercials; there’s nothing wrong with wrinkles. Your face ought to have some creases after fifty years of well-lived life. If it doesn’t, you weren’t using it enough.

But you want your skin to feel good, and as you age that means taking a little more care of it than you did when you were younger. Find a product or two that keeps your hide feeling supple and healthy.

If it makes you feel artificially slick or dried out, it’s the wrong product. A really basic moisturizing cream made from natural ingredients if often all a man needs. Lightly scented if you please — you don’t want it to clash with your cologne.

(You are putting a splash of subtle cologne on when you get dressed up at this point in your life, aren’t you? Work on that if you’re not.)

Looks the 50-Something Man Should Always Avoid

There are no completely hard and fast rules in fashion. Someone, somewhere, has probably pulled one of these off in his fifties. But you’re not him, and you’ll probably just look bad if you try. So don’t.

  • Sneakers/trainers. You’re done with ’em. Give it up and get over it. A pair for the gym or other athletic endeavors is fine, but unless you’re in a rock band and on stage, you shouldn’t be wearing athletic shoes as a style choice.
  • Neckties without jackets. This is a look men should avoid in general, but once you get into your fifties it can only make you look like a depressed, mid-salary cubicle worker with nothing left to live for. Very Death of a Salesman. Throw a jacket on if you’re wearing a necktie. For that matter, throw a jacket on if you’re wearing a dress shirt in general, even without the tie.
  • Sleeveless shirts. Even on the beach. Tank tops, especially the scoop-neck kind, should be firmly left behind as soon as your hair starts receding and/or going gray. And if you’re in your fifties and it hasn’t, good for you, but still don’t wear sleeveless shirts as your only upper-body covering.

Also worth avoiding is anything with too much of an “advancing age” feel to it — the really chunky orthopedic shoes we mentioned above, thick, dated eyeglasses, worn-out sweatshirts, or elastic-waist trousers.

If there’s something you need for your physical health, do it, and don’t ever let anyone make you feel ashamed of it. But go ahead and keep the element small and surrounded by other, purely aesthetic accents, so that it’s not defining who you are the moment people look your way.

Youth is almost always wasted on the young, but with a bit of sharp dressing, middle age can be made to work great for the man in his fifties. Have fun with it.


Written By Antonio Centeno
Founder, Real Men Real Style
Click here to grab my free ebooks on men’s style

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