A Man’s Guide to Dressing Sharp and Casual 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

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 20s30s40s, 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.

  1. 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.

  1. 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 bargain blazers from the sale rack at Large Retailers all look vaguely insubstantial — and the reason a man in the middle of them wearing a bespoke 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.

Written By Antonio Centeno
Founder, Real Men Real Style