Andy Richardson: Many hatty returns - it's time to get ahead again

Meh. I hear some of you say. And let's dwell on that irresistible three-letter word for just a moment. Meh is one of the finest additions to our vocabulary of the past 20 years. Used to denote indifference or boredom, it is the ultimate in onomatopoeiac expressionism.

That's a sentence I didn't think I'd write when I climbed out of bed at 6.30am this morning for another day in the Weekend hothouse.

But I digress. Hats is the theme of this week's erudition. So let's devote our attentions to the shaped crown and cropped brim. What's to like, I hear the Whitmore Reans posse shout? Hats are for Ascot – the women, not the horses, though it's hard to tell the difference.

Infidels. The lot of you.

Hats are cool. Hats are the rabbit hole that connect us to a glorious, golden era when Marlon Brando was the acme of masculinity. Hats return us to a time when pinstripe suit wearing, polka dot loving, stogie chomping, larger than life characters like Al Capone were style icons.

Hats are my shady past – but they might also be my glorious future. I'm willing to give hats a chance.

I acquired my first trilby from my grandfather, Alf, and it was smoking. Me and a couple of mates wore modish headgear on the mean streets of Tipton. The Specials had repopularised the pork pie hat and our trilbies upped the ante.

And then the wheels came off. I went through an experimental phase and made sartorially-challenged bozos like Ed Sheeran, Robbie Savage, Max George, Alex Reid and James Tindale look like catwalk courtiers.

My first hat disaster was a brown velvet number with embroidered animals on the side. I think I bought it from a craft fair. It wasn't a good look. Let's move on.

Worse was to follow. During my, Guatemalan Chic period – stop laughing at the back – I took to wearing a yellow silk number, brightly embroidered. As I walked along Walsall's Station Street at 7.30am each morning, past the hard-looking railway workers in their donkey jackets and steel-toe-capped boots, I looked like an explosion at Dulux. I'll never understand why someone – anyone – friend or foe, didn't just tap me on the shoulder and say: 'Mate, it's time to ditch the millinery'.

A Dior beanie was a step in the right direction. But mine was too small and – if I'm allowed to use the phrase innocently and without causing offence – it looked like a woolly condom.

After that, I sent myself to hat jail. I imposed a 10-year, tariff-free sentence. And I've been good to my word. The clock's ticking, however, and soon it will be time to reignite the fire.

I've seen two hats I like. The jazz singer Gregory Porter wears the first. It's like an all-in-one baggy cap with snood. He pulls it down so that it snuggles beneath the bottom of his neck. I'm guessing it's warm in winter.

Pharrell Williams takes the biscuit though. He wears the coolest post-Depression-era trilby that I've ever seen. Pharrell and me are brothers from other mothers. We've both had our hat disasters. Pharrell has worn furry deerstalkers, red and white beanies like Christmas baubles and, worst of all, a Louis Vuitton creation that looked like a picnic rug. Let me tell you, wearing a picnic rug on your head is just damn foolish.

But his new trilby makes him look cooler tha Steve McQueen, Paul Newman, George Clooney and James Dean rolled into one. Hope springs eternal. And if Pharrell can turn it around . . .

Andy Richardson