Looks for a man to master in His 50s

Bill Craig, Mens Clothing, Menswear, Suits, Near Me, Randburg, Melville, Johannesburg, A Man’s Guide to Dressing Sharp and Casual in His 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).

  1. 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.

  1. 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.

Written By Antonio Centeno
Founder, Real Men Real Style