Skip to Main Content
how to dress 50s male
how to dress 50s male
Required Reading

Dressing Your Age: How To Find Your Style After 50

July 27th, 2018

Style is a process, not an event

You’re going to be seeing some new faces and contributors here on HSS over the next few months. We’ve been wanting to add more voices and perspectives for a while now and today we’re pleased to introduce you to our friend, Mr. Andrew Poupart (but you can call him Andy).

You may already know Andy as the impeccably dressed man behind Style After 50 Instagram account and he’s here to regularly offer HSS readers his unique perspective on all matters of style. Please welcome him! –BTS

At some point, after about age 50, we enter a period of transition. Perhaps our children are grown and gone, perhaps we have more time and more resources to devote to ourselves and our partners. Perhaps we want to develop a style, a way of presenting ourselves to the world that reflects who we are now or who we want to be.

how to dress 50s male

Style is a process, not an event. I think it’s important to realize that one’s taste, and therefore one’s style, evolves over time and will continue to evolve. We are all subject to influences, consciously and unconsciously, and these influences shape our perception of how we want to present ourselves. Finding one’s style means finding a place where we are comfortable because being comfortable in one’s clothes instills confidence. And confidence is the secret to looking stylish.

So, here are five tips for finding your style after 50.

Stay in shape.

As we age, staying healthy and active is crucial to living a full life. Without our health we simply have nothing. Watch your weight, get a little exercise, eat a healthy diet. Much of style is about confidence, and confidence comes from within.

Learn about fit.

Well fitting clothes are important at any age but even more so as we mature. Clothes that fit always look good. Fit means clothes that are adapted to your particular body type. Fit flatters the good and minimizes the not-so-good. Good fit is the building block of style. Understanding what good fit is and how to apply those principles to your own body is very important.

how to dress 50s male

ANDY WEARS | Stephen Hitchcock suit, Budd Shirtmakers shirt, Shibumi Firenze tie, Simonnot Godard pocket square, Edward Green shoes

Don’t try to look young.

I’m not a young man. Every time I look in a mirror, that simple fact takes me by surprise. But it also means that I should not try to pretend that I am. Nothing looks worse than a man of 60 dressing like a teenager. Avoid skinny jeans, or indeed skinny anything. Ignore what you see in fashion magazines.

Don’t be afraid of color.

I adore color. I love anything red. I try to incorporate red into my style as much as I can. The sartorial staples of grey, navy blue, and brown, are excellent bases, but add a little flair and don’t be afraid to experiment with color. You’ll discover what works and what does not for your particular style.

how to dress 50s male

Seek out inspiration.

There are many examples of well-dressed men over age 50 and beyond. Hollywood has given us timeless icons of style, as relevant today as they were 50 years ago. Fred Astaire, Cary Grant, and Gary Cooper were all well dressed men their entire lives. Gianni Agnelli and Luciano Barbera are wonderful examples of stylish men well into their advanced years.

I’ve barely scratched the surface of the subject of style after fifty, but these tips are a good beginning.

Thanks for reading.

Stylishly Yours,
Photo of Andy Poupart

Andy Poupart

All Posts
Play/Pause Video

Big day. Big post. Extremely excited to share all the details with you. Here we go!

My tuxedo came from my good friends at Michael Andrews Bespoke, which may come as no surprise to regular readers as I've been working with them almost exclusively for the better part of the past two years. Over the past nearly six years, I've had the chance to experience many bespoke and made to measure suit programs and MAB is just head and shoulders above the vast majority of options out there.

He Spoke Style

We are the leading online destination for premium original men’s style content.

Our Story