Are you ever too old to wear a pair of short shorts?

What is ageless style and how do you achieve it? It’s an intriguing topic that continues to confuse women of every age.

The wonderful jewellery designer Chupi Sweetman recently posted a picture of herself on Instagram wearing a pair of denim shorts. She explained in her text below that when she first put them on her immediate reaction was, “I’m too old for these!” Chupi is 35, though with her lush long hair and cherub-shaped face, she looks considerably younger.

Irrespective of how old she looks or actually is, she touched on a topic that continues to perplex women of every age. How old is too old, or is there any such thing as too old?

Last month I hosted a live podcast on the very topic of ageless style, and one of the questions asked by an audience member was should a woman in her sixties wear a short skirt? I asked how she styles the short skirt? With a pair of white stilettos or with a pair of flat tan leather sandals? And where is she wearing that skirt? Is it on a sun holiday or to the supermarket on a Tuesday morning.

Listen: Ageless Style on Smart Casual 

Context is everything. I don’t believe in finite fashion rules. I believe in dressing for your personality and making the best of your good bits and minimising the bits you like less. If you approach your wardrobe with this framework in mind, you’ll hit the sweet spot whatever your age.

I’m 44 and I wouldn’t dream of wearing a pair of denim shorts, but that has nothing to do with my age. I’m an introvert and an inherently autumnal individual, so my instinct and my comfort zone are to cover up; palazzo pants and midi skirts are my go-to whatever the weather because when I wear these pieces I feel most like myself.

Photo: Marie Kelly via Instagram

Only this morning, a colleague of mine laughed at my commitment to lightweight knits through summer. I love knitwear and I always prefer to have my arms and decolletage covered. Again, this has nothing to do with my age, it’s just what I like.

In my twenties, I experimented with fake tan and clothes that weren’t instinctively “me” like strappy camisoles and sundresses and although I enjoyed this new me for a while, I soon realised I simply prefer how I feel and look in wide-leg trousers than I do in a sundress.

I have a friend who is a couple of years younger than me and she has always and will always be able to wear a khaki mini skirt. She’s a sun lover with a beautiful skin tone and she styles the skirt in such a low-key way, with a simple tee and leather sandals, that it looks completely effortless and chic.

In decades past, dress codes for women were clearly defined at every age. These days, there’s choice and there’s freedom and that comes with its own difficulties.

But if you stay true to who you are, what you like and what you feel good in, suddenly the choices become less overwhelming and the freedom more exhilarating.

That’s when you’ll achieve ageless style.

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