There comes a moment in every man’s life – usually somewhere around the first unsolicited senior’s discount – when he realises the clothes that once made him look rakish now make him look … optimistic. Dressing well in your 60s and beyond is not about chasing youth, nor is it about surrendering to elastic waistbands and synthetic polo shirts emblazoned with mysterious sailing motifs.
The goal, as ever, is dignity with a dash of mischief. You want to look like a man who knows who he is, not one who has wandered into Cotton On by mistake or, worse, the camping aisle of Aldi.
Here, then, are the do’s and don’ts of dressing well after 60 – with particular reference to real men, real bodies, and real Australian life.
DON’TS: Retire these quietly, preferably under cover of darkness
❌ Cargo shorts
You are not on active military service. You do not need six pockets. And whatever you’re carrying in them is not important enough to justify the silhouette of a startled wombat.
❌ Cheap graphic T-shirts
Anything with slogans, surf brands, skulls, or jokes about beer belongs either in the shed or the bin. Especially the bin.
❌ Shiny leather shoes
If they look like something worn by a wedding DJ in 1997, let them go. High-gloss leather is deeply unforgiving on an older man and suggests “formal occasion I no longer attend”.
❌ Ill-fitting jeans
Too tight looks desperate. Too loose looks defeated. If your jeans puddle around your ankles or require a belt tightened to within an inch of your life, they are not “comfortable” – they are wrong.
❌ The all-black outfit
Black drains the face as we age. What once said “cool” now says “tired but stubborn”.
DO’S: This is how grown men dress well
✔️ Invest in good basics
A proper cotton T-shirt in navy, white, grey or olive. A well-cut casual shirt. A decent jumper. None of these need to be flashy – they need to fit.
Australian brands like Country Road, R.M. Williams, Sportscraft, and Industrie (select pieces) understand male bodies that have lived a little. They cut clothes for men, not coat hangers.
✔️ Wear jeans – properly
Dark denim. Straight or slim-straight cut. No whiskering. No distressing. No elastic.
Brands like Neuw, Wrangler, and Levi’s 501 or 505 still do honest jeans for grown men.
✔️ Choose colour, calmly
You don’t need pastels or statement hues. Think navy, khaki, stone, charcoal, soft blues. These colours lift the face without shouting.
✔️ Jackets are your friend
A casual blazer, chore jacket or lightweight coat instantly elevates everything beneath it – even a T-shirt. It’s the fastest way to look put-together without effort.
✔️ Good shoes, quietly good
Brown leather lace-ups, suede boots, loafers, or clean leather sneakers.
R.M. Williams Craftsman, Blundstone dress boots, Clarks, or minimalist sneakers from Common Projects–style brands (without paying Common Projects money).
Brands that suit older men (without advertising it)
R.M. Williams – classic, durable, Australian, reassuringly grown-up
Country Road – excellent knits, shirts, and casual tailoring
Sportscraft – sensible, but often very good
MJ Bale – strong for jackets and shirts
Uniqlo – basics only; avoid anything “youth trend adjacent”
Patagonia – for weekends, not dinner parties
Style icons worth copying (the everyday Australian edition)
Forget movie stars in linen suits and Italian sunglasses. Look instead to men who dress well within their actual lives:
The well-dressed Melbourne café owner: dark jeans, white tee, jacket, leather boots
The coastal retiree who surfs “a bit”: chinos, knit jumper, worn-in sneakers
The ABC radio presenter: calm colours, proper shirts, nothing loud
Paul Kelly (the singer, not the journalist): simple, lived-in, quietly confident
Bryan Brown: the gold standard for ageing Australian masculinity – unfussy, relaxed, believable
Final rules worth remembering
Fit matters more than fashion
Quality beats quantity every time
If it’s comfortable and flattering, you’ve won
Don’t dress younger – dress better
The aim is to look like yourself on a very good day. Because style, like wisdom, should deepen with age – not unravel.
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