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The Year's Best Style for Older Men

Sharp, clean style for older men

Sharp, clean style for older men

Easy Style for Older Men

If you're a man on the good side of fifty—that is, the plus side—this brief and easy-to-use guide is for you. It includes both specific articles of clothing, as well as information and thoughtful suggestions from some of the most forward-looking fashion blogs and sites out there. I especially like the advice given by the foremost journal of male style, Esquire Magazine. I hope this article gives you some usable ideas on how to dress well, and how us older men can still make a statement with our style decisions.

Real style is never right or wrong. It’s a matter of being yourself on purpose.

— Bruce Boyer

St. George -- effortless style in the golden years

St. George -- effortless style in the golden years

Aging With Style: Some Basics

Looking like we still care—and we do still care, right?—means making some clean, clear decisions about how we want to look.

  • Older men like us are best off choosing one general look and then sticking to it. For example, if you feel good in a blazer and jeans, then don't ditch that style just because you're getting a little older.
  • Style stays; fashions fade. Instead of chasing trends, men our age can rely on a crisp white shirt, a pair of good-fitting blue jeans, and a sleek pair of brown cap-toe Oxfords. Add a slim-cut navy blazer if the occasion calls for it. That's easy style that has always looked good, and always will. Like us.
  • If you're in the mood, a subtly patterned tie is always appropriate for older men, and it will pull your look together.
  • Finally, we never wear white running shoes, unless we're out running. And even then, consider some black or dark gray Nikes.
Jack Black is my go-to brand for men's skin care

Jack Black is my go-to brand for men's skin care

Skincare for Older Men: An Essential Element of Style

There's much to be said for the older man who looks tough, wise, and masculine. The best men's skincare products let you look your age, without looking old. If you're an older man like me, here's what you need to know about skincare.

Shoe Choices for Older Men

If you're like me, you work in a place that has at least some dress requirements. Unless those requirements include a paper hat, you'll likely need to make some of your own decisions, and it goes without saying that you'll aim to look as sharp as you can.

Women, and probably everyone else, often look at a man's shoes first. That puts a lot of pressure on our shoe choices, but there's a reliable answer—the cap-toe Oxford. I like this shoe because it's dressy, but it doesn't sport the wing-tip stitching that, to my eye, has a rather aged and formal look. There are some excellent options out there that are both affordable and very good-looking, so let them start with your shoes when they size you up you'll be ready.


Cole Haan Cap Toe Oxfords

I love these Cole Haan Cap Toe Oxfords. They're sleek, stylish, and they match with everything. They're also amazingly comfortable, which makes them an excellent choice for work shoes that don't make people think that you've given up on looking good.

Reservoir Dogs: Rocking the vintage skinny tie look

Reservoir Dogs: Rocking the vintage skinny tie look

My Choice for a Slim, Sharp Blazer

Those of us with a good, sharp navy blazer in the closet will understand -- it's a style necessity. While it's not the only suit coat you need, and of course it's also not an actual suit, your navy blazer goes with everything and fits almost any situation. I pair mine with just about anything in my closet, but lately, I've favored a white or pale pastel shirt with very dark jeans or grey dress slacks. One of my favorite jackets is by Calvin Klein. I wear it all the time (I actually own three). It didn't cost me half a paycheck, it's durable, and the CK label means guaranteed style.

To me, style is all about expressing your individuality freely and courageously.

— Timothy John


To Go With Your New Blazer: A Sharp White Dress Shirt

A classic white dress shirt is a requirement for any well-dressed older man's closet. I like this 100% cotton pinpoint snap-tab collar shirt by Paul Fredrick. It's not cheap, at least by my standards – about $160 on Amazon – but there's no substitute for quality when it comes to looking your absolute best.

The reason I like this shirt for us older men is that it's not super slim-fit. There's a little room for us to breathe. Also notice that I have emphasized the fact that it's 100% cotton. A shirt with man-made fibers will eventually pill, turn yellow, and fray. Even at best, a non-cotton dress shirt will look like you found it in the budget bin. Which you probably did.

Here are the features of this cool dress shirt:

  • 100% Cotton
  • Imported
  • Snap closure
  • Machine Wash
  • Non-iron 2-ply Cotton Pinpoint
  • Snap Tab Collar, 1/4'' Top-stitched

Style Don'ts for Older Men

Here are some questionable style choices men make:

  • Skinny Jeans: Even if you're skinny, you should avoid them. We're older, and older men just look silly wearing these things. We are NOT the singer for Green Day.
  • Logo/Graphic T-shirts: After age fifty, anything emblazoned across your chest looks desperate—especially "funny" Threadless designs.
  • Hoodies: Bad for Bill Belichick, bad for all of us.
  • Long Hair: If you're losing your hair, any style that's more than 1/2 inch long is a big No. Yes, I said it. I myself am losing my hair, and I keep it cut short. It's the only humane option.
  • Wearing a Ponytail: If you still have your hair, anything that ties in the back should not even be an option (unless you own a yacht or produce pornos, in which case, go for it).
  • Overalls: Don't. Even if you're a farmer.
  • Blue Jeans and Running Shoes: This is my personal pet peeve. If you're going running, wear runners. If you're going to work, wear grown-up shoes.
Cool hand Luke, looking cool

Cool hand Luke, looking cool

Style Essentials for the Older Man: Quality, Not Quantity

It has been suggested—and I agree—that the most important thing about style for men past the age of fifty is quality and neatness. That's not to say that you need to spend an entire paycheck on a rack of Italian silk ties, but it does mean finding a few good ties and throwing down a few extra ducats for quality neckwear.

In general, your best policy is to buy a few very high-quality items and pair them in a variety of ways. It's always possible if you think about it and, more importantly care about it, to find ways to look better. We're not rich, but we're maybe not quite as poor as we were as young men. It's perfectly acceptable to spend a little extra style money to look good no matter our age.

Mr. Lauren is an excellent model for dressing in style as we age.

Mr. Lauren is an excellent model for dressing in style as we age.

Ralph Lauren: A Model Older Man

At least one men's fashion blogger has pointed to Mr. Lauren as an excellent model for dressing in style as we age. Ralph Lauren is, of course, the style star who, in 1967, obtained the Polo brand from Brooks Brothers, along with its iconic button-down collar shirt. Lauren was born in 1939, which puts him comfortably beyond our required age of 50, but he's still one of the most stylish, not to mention one of the wealthiest, men in the entire world. He oversees a multibillion-dollar business, as well as a pretty sweet collection of rare cars.

You don't need to dress with full Ralph Lauren style to succeed, but following a few of his habits won't hurt. You can start with crisp, long-sleeve button-downs (it's fine to roll the sleeves up), good loafers or lace-ups, and a subtle but quality watch.

Walk like you have three men walking behind you.

— Oscar de la Renta

The War on Our Skin: How to Protect It

A recent study, published by The National Center for Biotechnology Information, highlighted the incredible assault that our skin experiences every minute of every day. Aging skin is especially vulnerable, so men of our age need to be aware of the need to protect it. Some of the internal and external factors that affect our skin are genetics, cellular metabolism, hormones and metabolic processes, chronic light exposure, pollution, ionizing radiation, and chemicals. That's a full-on assault every day of the year. And if you're a little older, the effects are even worse. The redistribution of fat through gravity and the loss of bony skeleton support affects the shape and condition of your face.

When we've been on the planet for more than a few decades, it all adds up. Our skin has a little more "give" and a few more wrinkles. These are hard-earned marks of character, experience, and power, so why would you want to inject or cut them away? Treat your skin well with a quality moisturizer, and leave it at that. Let your face tell people that you've had an interesting life. I recommend the Jack Black Double-Duty Face Moisturizer with SPF 20. It is lightweight and protects you from aging sun rays.

Hair for Older Men: Less Isn't Always Less

As we age, our hair and skin do some interesting things, but don't assume that all of them are bad! It's no tragedy if a man over fifty loses some, most, or even all of his hair. It comes with the territory, and there's nothing to be gained when an older man acquires a too-new head of hair. How you groom yourself must be grounded in reality. You show your confidence and power by embracing your age, not denying it. So keep thinning hair very short, and longer hair styled with restraint.

We work with what we’ve got.

We work with what we’ve got.

Trim Those Nose Hairs, My Friend

We can dress and accessorize correctly for our age and do everything else right, but if we don't pay close attention to necessary grooming details, then everything else will be done in vain. As we get older, unfortunately, nose and ear hairs begin to proliferate. They may seem small, but trust me, people notice them. If there's one thing that makes an older man look old, it's out-of-control nose and ear hairs. These hairs grow faster and more wiry in older men, and if you don't stay ahead of them, pretty soon you'll look like a hairy old troll. Trim them back and you'll instantly be miles ahead of all the other men your age.

It takes a good hair trimmer to do the job, so please don't buy the cheapest model because these tend to yank and tug. While in some contexts that can be just fine, it's no fun at all when it comes to nose hairs. I have used both a low-quality and a professional-grade nose trimmer and there's really no comparison. The professional models snip hairs off with no pain.

Think Twice About Men's Style and Aging

I'm a man who will not see 50 again, and I'm perfectly fine with that. I don't have my head in the sand, and I'm aware that dressing well as we age can be a little tricky. Last decade's suit and casual combos may not be appropriate anymore. But we can always do better, and as we gain years and wisdom, we also gain the power of experience. It seems to me that older men like us should dress in a way that reflects both our knowledge of how to do things and the fact that we still have the ability to do them. A tasteful, elegant, yet affordable style for older men isn't a mystery, but it does take attention to detail and the help of a few well-chosen sources.

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More Style Articles for the Older Man

Questions & Answers

Question: Where can I find structured blazers that aren't too formal in the Southeast U.S.?

Answer: I have an online account at Nordstrom Rack, they have good blazers at great prices.


GreenMind Guides (author) from USA on July 26, 2019:

Hi -- older men should always wear round or crew-neck T's. V neck T's, in my view, are for much younger men.

Sharon Packer on July 11, 2019:

Question: What type of undershirt should a man over 60 wear? My husband likes to wear a wiki t-shirts and thinks that rounded colors are fashionable. I'm not sure about that. Our sons who are in their 30's say a v-neck is better. I would say that my husband doesn't have a long neck and that the rounded neck t-shirt looks too prominent. Also, what color should an undershirt be? Is a dark color ok if the color is open? Can you please suggest specific company names for these t-shirts. Thanks