As you look in the mirror and see the creaking shadow of your dad’s eggy head approaching, it’s time to hide it with a big hat

When your remaining hair begins to resemble a small cluster of Caribbean islands on a map of the world, there are a few options. 1) Monster-era Michael Stipe, when he went pre-emptively bald, breaking teenage hearts and ushering in the end of REM as we knew it. 2) Wear a hat.

And when I say, “Wear a hat”, I mean it literally as well as euphemistically. Because, to be blunt, we all know that when a man of A Certain Age begins to wear hats, it’s a sartorially polite way of saying, “Hey, guys, I’m doing the slow, swimming pool walk towards hair loss and I’m trying to cover it up with a Justin Timberlake SexyBack trilby. DOYOUTHINKANYONEWILLNOTICE?!”

And I think that, yes, yes they will.

So here we stand, after attempting comb-over, comb-under, comb-round, short shave, overgrown. The time has come to wear hats. This equates to an acceptance that your best hair days are behind you (probably lying on your pillow or matted sadly in a hairbrush). As you look in the mirror and see the shadow of your dad’s head approaching, you know you need to hide it with a big hat.

It’s the least subtle thing in the world, and yet some hats are actually quite nice.

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The Frank Spencer/Che Guevara beret has been on the Prada catwalk and seen on the likes of Miguel. Meanwhile, the perennial “Mani from the Stone Roses” bucket hat was spotted at the Supreme and Barbour shows. Wearing the latter, I feel as if I’m walking about with a subtitle draped around my neck that reads, “Lad (1997-2004)”: you don’t have to be mad fer it to wear a bucket hat, but it certainly helps.

With a beret on my head, I feel “peak fashion” – that is to say, I would expect to get a few quizzical looks if I wore one down the high street. Still, I reckon it’s a pretty sharp alternative to baldness.

Conversely, the sheep’s fabric bobble hat I’m wearing feels nicely in the middle ground, as if I’ve placed Winter Wonderland atop my head and am parading it around. It lifts the whole look, even though I’m getting certain “East 17’s Brian Harvey wears a bobble hat” vibes from the whole thing. No bad thing.

Styling: Melanie Wilkinson. Grooming: Sam Cooper at Carol Hayes Management.

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