As the years fly by and the flecks of grey hair become more like waves, it’s easy for a man to slip into a uniform where comfort is king. 

Some men are still attached to a well-loved pair of Amco jeans bought back when Dennis Lillee was still storming in from the Paddington end, or items featuring the word 'elastacised' and the wonder that is poly-cotton. This is especially tempting in retirement if you happened to have spent 48 weeks a year during the previous decades in a suit and tie.

But while there’s much to be said for the convenience of this approach, why do advancing years and sharp style need to be mutually exclusive? In fact, you now have the freedom and budget to sartorially express yourself with greater liberty than at any point in your life.

Before we detail why, here’s a task: next time you’re at the local mall, take time from wondering why anyone would want to add salt to caramel or freeze yoghurt, and check out the confused faces of younger men as they peer into the windows of menswear stores.

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Cary Grant, one of the world's best dressed men (Image: Wikimedia / Farid_S_V)

It comes down to two words: Mad Men. Although set in the 1950s and 1960s, this television series redefined contemporary masculinity for a generation raised on acid-washed denim and hypercolour t-shirts. They yearned for the effortless elegance of all those things you probably just did as a matter of course. The tie clip, the pocket square, the tweed sport coat, the razor-sharp pants crease, the cuffed pant, the signet ring, the cufflinks.

Point is, the outfit you probably wore to the office or a weekend barbecue back in the day would now take a team of stylists to conjure.

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Dressed to impress: Humphrey Bogart

What’s more, unless your wardrobe has been regularly expunged – something that’s as rare among men as stacking the dishwasher to their partner’s satisfaction – it’s probably teeming with gems a contemporary hipster would give their single origin latte for. Just call it “vintage” instead of “old” and you’re halfway there.

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A true male fashion icon, actor Clark Gable 

Aside from the treasures already in your cupboard, you most likely grew up under the influence of the last great generation of male style icons – Bogart, Grant, Gable – and better examples you couldn’t ask for. Whether it’s cabana wear or the full 'bag of fruit', the look that’s most likely second nature to you and require just minimal effort is now being celebrated as the height of sophistication. Better still, who amongst us doesn’t walk that little taller and step a little brighter in an outfit that’s got a bit of old-school sass?

So, pop on a Panama, strap on that Timex you got for your 21st and reach for a spritz for Aramis. In other words, break out the good stuff, dress up for the sake of it every now and then and bask in the admiring glances that surely come the way of a well-dressed gentleman of a certain age. We tip our hat to you, sir.

(Feature image: Facebook / Mad Men)

Join the conversation – who is your favourite well-dressed man?