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.
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.
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.
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.