Here’s some notes that I collected over the years, and pulled together for myself. It’s just some thoughts, and some guidelines that I collected in a file that I promised myself that I would get to “one of these days”. On Saturday, I was going though a dusty old hard drive and found this collection. And so, I decided to “put it up there” for everyone to read and (perhaps) to scoff at. (Hopefully not.)

Now, I have gone in and out of fashions and styles all my life. There were times when I was truly fashionable. Such as the bell-bottom, long-haired 1970’s, and the cargo pants and layered pastel polo 1980’s. This evolved over time into the early 1990’s when I was wearing pencil thin neck-ties, double breasted suits and mullets. And so on and so forth.

But something happened to me.

Maybe it was prison.

Maybe it was no longer working in a corporate environment.

Maybe it was China.

Or maybe it was when my facial hair started to turn grey.

There comes a time, in every man’s life, where you take a step back and say, “well, I just want to wear clothes that are comfortable, and where I look good in them”. And that is what caused me to generate this collection of guidelines.

Don’t you know…

Introduction

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.

Although you all have to admit that being of legal age to do everything is always an improvement.

When you start seeing your hair turn grey (or white) is 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 Attire

Your business wardrobe is your business wardrobe. Sigh. It’s dictated by the necessity of your profession. Whether you wear a uniform, or meet the company “dress code”. 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.

Don’t go on confusing “casual” with “sloppy”.

Big mistake.

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 some things an older man wants to keep in mind when choosing his casual wardrobe:

[1] Fit

Wear ONLY clothes that fit you well.

Do not wear clothes that don’t fit.

Do not wear clothes that are too tight. Or clothes that are too big. You wear clothes that fit you well. I know that you all probably have nice clothes that cost some money, but you never wear because they don’t fit you well. But you keep them anyways.

Throw them out or give them away.

By this decade of your life, you should have a very good sense of your body.

[2] Tailoring clothes to fit you well

I go on the internet, and especially on English websites, they talk about having a tailor make some perfectly fitting clothes for you. How wonderful! But let’s face it, most men don’t have a few thousand dollars to dedicate to this. And having clothes that fit is not on the main list.

Instead, it is on a secondary list that includes chores, repairs, and special purchases for the family. And at that, unless you are single, it’s at the bottom of that list.

But think a minute.

If you had no other issues; no other attachments, wouldn’t clothing rank as your top priority after food? (Fine, delicious food, by the way.)

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.

They don’t cost a lot of money.

In the days when I worked for a massive automotive electronics company, our dress code was a white shirt and a red tie. But I made sure that I would buy off-the-shelf high quality shirts, and then spend a few dollars having each one tailored to fit me exactly. It did make a difference on how I looked and felt about myself.

Get everything trimmed to fit you.

Shirts, and trousers are mandatory. Suits and jackets go without saying. 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.

Oh, and don’t be afraid to toss old underwear, too. And, ladies… this includes old bras. Toss those fancy wire things that you love that never wear, and those bras that are old, and frayed. Go get yourself a nice VERY WELL fitting bra. Make sure that you have the right cup size, and the right under boob width. Wearing a comfortable bra makes all the difference in the world.

Or, so I am told.

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 when you get old 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. (It’s a guy thing, don’t you know.)

[3] Comfort

I wear black tee-shirts all the time.

But that’s just me. When they get old I toss them and get a newer one. These are plain black shirts that fit me well, and that either have a small logo on my left chest, or an embroidered pattern. I rarely wear large garish patterns, or designs.

Again, that is just me.

And remember that I live in the tropics. Zhuhai temperatures are much like Singapore. We have two seasons. Warm, and very Hot and very humid.

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

A lot of looking comfortable in your clothes comes down to actually being comfortable in your clothes, but you can do a lot with tailoring and styling too.

For those of you who still wear suits, and even I do from time to time, 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, try relaxed looks like sweaters and knitted tee-shirts, or other more relaxed shirts. You just need to move away from the business-standard dress shirt and its turn-down collar (and tie) ensemble. (Burrr.) Handsome, well-fitted clothing that’s obviously made for leisure tells people that you’re prioritizing your own pleasures.

A man who is comfortable, will look comfortable.

A man who is happy, and confident, will look happy and confident.

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 clothes that fit your personality; grown-up clothes, just buy them in soft fabrics, relaxed cuts, and a nice casual variety of colors.

[4] 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, decades of putting fabric on your body gives you some idea of what feels good and what feels cheap. And of course you know this. Don’t you?

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.

[5] Some “Looks”

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).

For me, I tend to wear (and keep in mind that I am in the topics), a nice well fitting black tee-shirt, and long well made (hiking) trousers. I wear with a special kind of canvas loafer local to China, and accessorize with my (good will energy) bracelet, watch, and belt.

With that in mind, here are a couple of looks that will always look good on a man in his older years…

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 don’t you know. 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.

But what ever you do, don’t look like a used car salesman!

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.

When I wear a suit, I always simply wear a black blazer over my black tee-shirt. It’s simple. I’m dressed up. Ya gotta problem with that?

For a real impression, I buy a brand new crisp white tee shirt. Then wear it instead of a black one. You gotta break out of your mold every now and then, don’t you know.

Shirts. I do wear them from time to time. Especially when the temperature drops below 90C (30C or so).

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).

The Stroller

A “stroller” is an older phrase for daytime semi-formal wear, especially for being out and about — truly strolling somewhere.

It’s really a cool thing to do. But what ever you do, don’t clasp your hands behind your back, carry a boom-box playing forty-year old pop music, or wear pristine white tennis shoes as you do so.

Not recommended.

You should own a good walking outfit, or several, because frankly a man in his silvering years 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 trousers and nice clean top, and a good pair of walking shoes, and then…  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 (come on!) you can do better than that.

Besides, if a fine attractive lady and you strike a nice conversation, take it inside and enjoy their company over some delicious food!

The Silverback Badass

Style in your older years (not ancient years) 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. An older gentleman 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. 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? You gotta problem with that?

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.

Here’s some things that an older man should own by now…

Given your environment, obviously.

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?

Yeah. I tend to dress in dark colors and when I am wearing a black blazer over my black tee-shirt, a few nice black scarves really makes the outfit “pop”! And it’s a great conversation piece with the ladies.

Scarves as a style piece rather than a functional necessity are a direct descendant 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 later years.

Suede / Canvas topped Shoes or Boots

I have been told that I’m done with sneakers and court shoes at this point in life, except for on the actual court. But that is ok. Suede / Canvas toppers are 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, 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…

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. I use moisturizing cream twice daily, and I live in the tropics. If I didn’t my face would probably look like the grand canyon with all sorts of deep crevasses and wrinkles from my days of working the chain-gain at Brickey’s East Arkansas Regional Unit’s Hoe Squad.

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 to avoid

There are no completely hard and fast rules in fashion. Someone, somewhere, has probably pulled one of these off in his later years. 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. (Though, I do wear them in the house as house clothing in the impossibly hot Summers of the South China Sea.)

Also worth avoiding is anything with too much of an “advancing age” feel to it — the really chunky orthopedic shoes, thick, dated eyeglasses, worn-out sweatshirts, or elastic-waist trousers. Oh, and don’t forget to toss that Alice Cooper Tee-Shirt from 1971.

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. You might be surprised how well you feel, how well you look, and the kinds of people you will meet and strike up conversations with. You never know.

Do you want more?

I have more posts like this in my Happiness Index here…

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