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‘What the hell should I wear?’ The style challenges of a fortysomething man

The certainties of youth are slipping away and I find myself in something of a clothing identity crisis. It doesn’t help that what’s ‘cool’ is increasingly hard to pin down. So where does that leave an average bloke just hoping for the best?

In September I will turn 44, the supposed first iceberg of ageing. As my own personal A23a approaches, I find myself, when it comes to how to get dressed at least, not older and wiser but but more adrift than ever.

It’s not necessarily for want of effort. A while ago I tried on a pair of wide trousers: the big blocky sort that have become increasingly fashionable. I hadn’t worn anything like them before and wasn’t convinced, but was feeling bored with my own wardrobe. When I modelled them in the shop for my wife, she reacted instantly. I couldn’t pull them off, she said. You’re not an art or fashion person, was the implication. She was right; her advice tends to be sound.

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