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The Best Style Advice for Men Over 50

I have worked hard to stay fit and understand the complex relationship between aging, nutrition, and exercise.


Ageless Style for Older Men

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 style for men over 50, along with some very solid reasoning about why we should still care how we look.

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 style decisions. It's the confidence and calm of an older man that radiates power. Don't sell yourself short, my friends!


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

— Gore Vidal

You Need to Get a Pair! Of Sharp, Timeless Shoes, We Mean.

I love a sharp pair of shoes, but as an older man, I know that I can't wear every new style the comes along. Those shoes really belong on the feet of a younger man. One of the best ways we can show that we still care about style is to be very aware of what's on our feet. You can do everything right—slim, flat-front trousers; fresh light-colored dress shirt; dark two-buttoned tailored blazer—but if on your feet is a broken-down set of dingy loafers, your efforts will amount to nothing. People see shoes, folks. They're going to see yours.


Cole Haan Wing-Tip Oxfords

This is why I heartily endorse wing-tip Oxfords for older men. This is a style that simply always works with whatever you're wearing, whether a suit or jeans. Wing-tips are dressy, but not in a pushy or trying-hard way. Men over 50 can wear them with confidence, and you can't always say that about the fluffy treads that you see on the silly-skinny-suit dudes on the train every morning. Leave the faux-buck and the pastel soles to those who still spend triple digits on hair product. Our wing-tip Oxfords tell the world that we're comfortable with who and where we are. Older men are like a classic film: when we walk out into the world, it becomes our movie set.

I own several pairs of Cole Haan wing-tip Oxford lace-ups. Cole Haan is an excellent brand, always in style, not too expensive but definitely not bargain bin. Getting dressed with a few pairs of CH shoes in your repertoire is a pleasure, not a challenge.

Comfort and Joy

There are a number of reasons why I like Cole Haan shoes, and one of the biggest has nothing to do with style—they are insanely comfortable. I'm an older man, but I'm also a teacher, so I'm on my feet more or less all day. 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 pretty much all us older men have, I have virtually no discomfort. And I know I look good, too.


The Good Side of Fifty

As a man who is on the better side of 50—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. Well, maybe partly because of that. But it's also because he has style!

This guide offers some ideas about fashion and style for the older man. We're not talking Paris runway here—just good-looking, clean, affordable style 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.

The Timex Expedition Wristwatch

The Timex Expedition Wristwatch

Wristwatches: A Solid Choice

You'll need a watch, and unless you're the kind of older man who drives a edge-of-silly sports car and pays $300 for a haircut, you'll need to keep the price under control. Consider the Timex Expedition Metal Field Watch, which will tell you what time it is AND make you look rugged and adventurous, all for under $50. Timex may seem like a bit of an obvious choice for an older man to put on his wrist, but the Expedition looks anything but dated. Also, as it turns out, Timex has a history of pure innovation and daring: in the mid-19th century, when everyone else was still making their timepieces out of wood, Timex began using stamped-metal parts and an early version of the assembly line (it was so effective that it may have influenced a certain young car manufacturer named Henry Ford). Timex may seem like an elder statesman now, but the brand has a wild, rule-breaking past that few youngsters suspect. Kind of like – well, you know.

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Gentlemen, Get to Know Your Tailor

Tailored clothes—this is something your average older 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! You can immediately start looking better. It's not all that expensive, certainly less than trying to update your style by replacing your older clothes. Take them in, get measured, 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.

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 style 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. Most younger men have yet to discover the joys of tailoring, but older men should know the difference it can make.

Gentlemen, Get Yourself a Slim Navy Blazer

This item should be in every man's closet, and even if you have one, there is most definitely room for another one. Like a good pair of wing-tips, a sharp navy blazer goes with everything and automatically makes an older man look good.


If You Can Pull it Off...

Full disclosure—I have spent the last few years working on losing weight and staying lean, so now at age 57, I'm in pretty much the best shape of my life. This isn't as hard as everyone makes it sound! Take the long view and give yourself at least a year to turn the ship around. You can do it. And if you're an older man who's still in decent shape, good for you! Not many of us are, sadly.

If you can pull it off, by all means go for a slim suit coat or blazer. Too often, men over 50 automatically choose a full-cut blazer that looks baggy and boring. Think for yourself, and if you look good in a slim-cut coat, then by all means get yourself one!


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 a sad pit of style conformity. 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. You could start by ditching the older items in your closet! Upgrade with anything that shows the world that you're still thinking about how you look, and that you still have style.


Jeans and Running Shoes—Don't Do It!

Wow, do I ever 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 an older man 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 style, 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 worldwide 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 style choices.

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Poppy from Enoshima, Japan on November 13, 2018:

Excellent article. I love your writing style; it made me laugh!

You are absolutely right that men over 50 have experience and wisdom even though they met not be as fresh-faced as their younger counterparts. Really, men on the (as you put it) "better side" of fifty have much more confidence and satisfaction with who they are, which is very attractive.

My husband will be fifty in just a few years and he dresses very well (unless he's at home, then it's all about the Hawaiian shirts and shorts). He doesn't wear a suit to work, per se, but he always dresses in smart trousers and shoes and often a blazer or jacket with a pocket handkerchief.

Knowing how to dress that 1. Makes you look good and 2. Is appropriate for your age is very important. I know nothing about fashion, but my husband seems to have gotten these tips you suggested down to an art.

Oh, also, blue trousers and running shoes DO say "surrender!" What a great way to describe it. Another one that makes me cry is the socks and sandals combo.

Epa Mustopa from Indonesia on August 27, 2018:

Waaw. it's nice reference. Thanks

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