Fashion and Style for Men Over 50

Updated on November 24, 2017
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I have worked hard to stay fit and understand the complex relationship between aging, nutrition, and exercise.

Fashion and Style Ideas for the Older Man

We're aging, guys—every minute of every day. But that doesn't mean we have to give up on looking good. This article is a quick and easy guide to some of the more important things we can do to make sure that older men like us stay in the game.

It's true that men's style can be a tricky thing, but remember that our best feature is our intelligence and experience. The young studs may have their thick hair and wrinkle-free skin, but we have something far more valuable than that —we've been there. We know. We have the judgment and experience to guide us in our decisions. It's the confidence and calm of an older man that radiates power. Don't sell yourself short, my friends!

As a man who is on the better side of fifty—that is, the other side—I know that the options for fashion and style for older men can seem pretty slim. Too often I see men my age going about in high-waisted "mom" jeans and white running shoes. It doesn't have to be that way! We need to ask ourselves: Would George Clooney step out in ill-fitting pleated Dockers and whatever polo shirt happened to survive the latest struggle with the dryer? Nope, and not just because he has tons of cash.

It doesn't take a lot of money to dress like you care.

This guide will offer some ideas about fashion and style for the older man. We're not talking Paris runway here -- just good-looking, clean, affordable looks for older men who still care about how they look. I hope you find some items here that will work for you, or at least some starting points for ideas that will work with the wardrobe you already have.

Style is knowing who you are, what you want to say, and not giving a damn.

— Gore Vidal

My Number One Element of Style: A Good Pair of Wingtip Oxfords

I love a stylish pair of shoes, but as an older man I know that I can't wear some of the newer styles; those shoes really belong on the feet of a younger man. So I always go for classic style, but not boring, old-man shoes. I also really avoid trends, like those suede numbers with the colored soles. Instead, I own several pairs of Cole Haan wing-tip Oxford lace-ups.

There are a number of reasons why I like these shoes, but perhaps the biggest one is that they are insanely comfortable. I'm a teacher, so I'm on my feet more or less all day, and Cole Haan makes shoes that I forget I'm wearing. With the step counter on my phone, I have counted up to 20,000 steps in a single day -- almost ten miles! -- and aside from the usual creaky knees that we all have, I have virtually no discomfort. And I know I look good, too.

Gentlemen, Get to Know Your Tailor

This is something your average guy never really thinks about – but we're not average, are we? If you know where your dry cleaner is, you know where your tailor is. It's time to take an armload of clothes down there, get a few measures taken, and boom! immediately start looking better. It's not expensive, and your tailor will have it all ready for you in a matter of days. Even if you just take in a few pieces, it will make a difference in the way you look, and especially in the way you feel.

The Bespoke Suit

Guides such as Esquire's "What Every Man Should Know About Fashion" more or less insist that we should each own at least one bespoke, or custom-created, suit. I think that's a noble goal, but these suits are generally quite expensive, and they're not going to last forever (and neither are our dimensions). So as a good substitute, please at least make sure that all of your suits have visited the tailor with you inside them. The adjustments, even the little ones, made by a good tailor will make a considerable difference in how the suit looks.

The Navy Blazer: A Style Essential

I sometimes feel like I live in my navy blazer. This iconic element of style suggests confidence, restraint, and power handled with intelligence, and whenever I leave the house in one I feel ready for the day. A quality navy blazer, like this sharp wool jacket by Hugo Boss, will never go out of style and will always make you look good. A bonus -- navy and other dark colors are slimming, and a well-constructed suit coat or jacket emphasizes a man's shoulders.

Reinvent new combinations of what you already own. Improvise. Become more creative. Not because you have to, but because you want to. Evolution is the secret for the next step.

— Karl Lagerfeld

Why Older Men Should Step Up

The world needs patience, wisdom, and kindness -- and older men have these great qualities in abundance. As an older man, it kind of drives me nuts when I see other men my age who have clearly given up and decided to follow the herd into fashionless anonimity. If that's truly what you aspire to, then totally fine and enjoy the peace of not trying. But if you're not quite finished yet, consider moving your fashion sense forward a little bit. It really doesn't take much – a new jacket or two, something other than blue jeans or those tired pleated Dockers, or even just a new watch. I'm talking about anything that shows the world that you're still thinking about how you look!

Jeans and Running Shoes—Don't Do It!

Why I Hate This Look

Fashion is a highly individual decision, so my own prejudices do figure in to my take on this issue. But there's something about running shoes and blue jeans on a man of a certain age that looks like surrender. If you disagree, that's fine. But the next time you're out, look around at the bottom half of the men passing by (discretely, of course). See how many are sporting the running shoes and blue jeans look, and ask yourself if you're happy looking like everyone else. Maybe you are! But if you'd like to stand out from the herd a little, and get noticed a little, then consider taking a little leap and rocking a pair of flat-front chinos and a comfortable, fashion-forward pair of shoes. It doesn't matter where you go or what you're doing – the old rule applies: “Look Good, Feel Good.”

I'm Not George; You're Not George...

Looking as good as George Clooney isn't an option for us mortals. But there's a vast area between St. George and complete surrender, so why not occupy some of the territory in between? Let world-burners like George, Sean Connery and Harrison Ford be the stars, but let's shine a little light ourselves. Clean, crisp lines and a thoughtfully chosen wardrobe is all you really need.

But We're Also Not Bill Belichick!

Are we? No? Good. So let's avoid looking like him, alright? Every time I see this guy I want to smack some fashion sense into him. I understand that it's cold up in New England, and I know his mind is on the game, but there has to be a limit. Someone get this guy a parka, at least. It hurts having a representative of our male cohort going out into public -- actually, on world-wide television -- looking like he just rolled off the couch and hasn't yet brushed the Cheeto crumbs off his chest.

Fashion is not necessarily about labels. It’s not about brands. It’s about something else that comes from within you.

— Ralph Lauren

Good Luck, Men!

Now let's get out there and make good choices.

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