Dressing Your Age: How To Find Your Style After 50

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,

Andy Poupart
He Spoke Style


Chime In

  • RJ Giddings

    Excellent article. Precisely why I like HSS. Thanks !

    • http://hespokestyle.com/ Brian Sacawa

      Thanks so much, my man. Big things coming in the next two or three months.

    • Andy

      Thank you!

  • https://littleblackdomicile.com Little Black”domicile”!

    Oh how we wish more gents were bespoke! Andy makes us smile each time we see him. Often we use fashion for our interior design inspirations….good design is every where and for everyone.

    • http://hespokestyle.com/ Brian Sacawa

      Very cool! We’re very happy to have Andy on the team.

    • Andy

      That’s very kind of you! Thank you.

  • Tom B

    Congrats on getting hitched, Brian!

    And great article from Andy. As an over-50 guy myself, I’m happy to see some styling for us VINTAGE gentlemen. Definitely the older I get, the more fun I’m having with clothing, in large part thanks to this blog. I couldn’t agree more about how little pops of color or detail do everything to ring the changes on a base grey, blue, or brown. Likewise on staying healthy and being careful of fit. The rest is just having fun!

    • http://hespokestyle.com/ Brian Sacawa

      Thanks, Tom! Good to hear from you and I feel like I owe an apology for the lack of regularity recently. There are some very interesting things in development, which should become evident in a month or two.

    • http://hespokestyle.com/ Brian Sacawa

      But one of those is more contributors!

    • Andy

      Thank you for the feedback!

  • Robert Ferguson

    I’m a suit fitter myself and I’ve been building up articles for my father to look over.
    This is fantastic, he’ll enjoy reading this!

    • http://hespokestyle.com/ Brian Sacawa

      Excellent! Glad to be of service.

    • Andy

      Thank you!

  • Harish Thakur
  • http://stylesprinter.com/ Katya Bychkova | StyleSprinter

    Congrats! I think this looks nice and neat.

    StyleSprinter Blog by Katya Bychkova

    • Andy

      Thank you.

  • Forrest Howe

    Another great article. For color I also add pastels like pinks and lavender. They brighten up ones wardrobe without dominating.

    • Andy

      I agree. Pink, especially, is an excellent addition to any gentleman’s wardrobe.

      • Jerry Gallo

        The key word here being ‘gentleman.’

  • AJH

    Wonderful piece, thank you. Incidentally, can you share the name of the artist behind the painting in the background of the first picture?
    Many thanks,

  • https://www.malesensepro.com Eric White

    I never thought of the topic… but indeed he is looking way better then I ever did… thanks for the article saving it for my 50 birthday :)

  • Jerry Gallo

    I agree with everything, and even the order presented. One thing I struggle with though is that many young people dress in a very casual way. I as an older gentleman (at least I try) I tend to be more formal. I don’t want to look ‘old’ but I don’t want to look too casual either. And I certainly don’t want to look like I’m trying to look young. So I now wear more knit ties and fewer silk foulard ties; more blazers and fewer suits; more walking shoes and less of the oxford dress shoes. But I’ve added some nice Rolexes and sometimes wear a pocket square, little things. Things that the millennials wouldn’t even notice, but other older people would notice.

  • https://www.instagram.com/beardedfancyman/?hl=en beardedfancyman

    Before dressing, I just ask myself: WWASD?
    (What Would Alessandro Squarzi Do?)