Dress like you’re older, not younger

I’m in my early 40s, but I aspire to dress like some men in their 60s.

The author at a recent Holt Renfrew Men event in Toronto. Photo by Malestylepro

By that age, men who care have found their sense of style and how to express it. They tend to wear clothes that aren’t as tight-fitting, not only because they are a bit heavier-set, but because they’ve realized the drape of extra fabric is very elegant. And chances are, they’ve come to understand what is self-expression as opposed to following a current trend. By dressing like I am 20 years older, I can hopefully age into my wardrobe.

The always impeccably dressed - at any age - Duke of Windsor.

The Duke of Windsor, dressed impeccably at any age.

There are far too many men in their 40s who dress like guys in their 20s. At that young age, guys are usually early in their journey towards developing a personal style, and they express all the pitfalls and miscues of youth. Like sticking too close to a trend they will laugh at in a decade. But on a 20-year-old, that’s commendable self-exploration. On a 40-year-old, I believe, it can make you look even older because your clothes are so clearly meant for a younger figure and lifestyle.

All that said, “dressing for your age, not your shoe size” doesn’t mean boring. Colours and combinations are endless, but wear them with a lot more thought. And make sure your clothes fit your older, more mature body.

Embrace ageing as an outward symbol of how much you’ve learned and matured on the inside. Don’t run from it. Because you can’t.