09/11/2011 18:30 GMT | Updated 09/01/2012 05:12 GMT

I Would Like A Hat Like That

I have a confession to make. I own a lot of hats. We're talking in excess of single figures here - at the last count there were at least 20 of them. It's not a big or particularly troubling confession to make and I'm sure people aren't really shocked by it. The main problem is this - not a single one of them suits me in the slightest.

I'm an inveterate hat tryer-on-er though, if I pass a pile of hats in a shop, I just can't help picking one or two up and admiring myself in a mirror, realising I look ridiculous and then feeling disappointed. It can be any kind of titfer - from a porkpie to a top hat or a bowler to a fez (which, so they say, are cool) - it'll be plonked on top of my skull just to check that reality hasn't warped in some peculiar way, changing the shape of my head and face and that, yes, I still look laughable.

The closest I've ever got to wearing a hat with some style was a flat cap I used to screw onto my little round head, before I realised I was just confirming all kinds of regional stereotypes. All I needed was a whippet and a bucket of gravy and people would immediately stop and point like Donald Sutherland at the end of Invasion of the Body Snatchers except, instead of a harrowing unearthly scream, they'd hiss the word 'Northern' at me.

Most of the hats I've owned have been of the beanie variety, a hangover from the days when I had ridiculously long hair and could get away with pulling them down over my ears, without fear of looking like Ross Kemp's runt of a brother on one of his away days in Afghanistan. When I wear one now, and catch sight of myself in the mirror, I have the oddest desire to mutter "Yes, Miss Diane" in an unconvincing Brummie accent. Now there's a reference no one under the age of 30 is going to understand.

I'm also rather fond of hats with earflaps, having grown up devouring reprints of Sherlock Holmes adventures, featuring the beautiful Sidney Paget illustrations from The Strand of Holmes in a deerstalker. Again, I can't actually wear a hat like that without looking like a complete idiot. Actually, I don't think anyone can wear a hat like that without looking like a complete idiot. John McCririck, I'm looking at you - and, to be perfectly frank, I'd rather not be.

The main problem I have with hats is that the way I dress - what I loosely describe as 'crumpled kidult', and other people less charitably call 'scruffy' - doesn't lend itself to a more stylish hat. I couldn't wear a fedora with a fleece or a trilby with a t-shirt. So, in order to actually be able to wear a hat that vaguely suits me, I'd have to change my entire wardrobe. I'd have to ditch the comfy jeans and jumpers that have been my staple attire for the past 20 years and start wearing suits, and maybe even - oh, the horror - a tie. And I don't think I'm quite ready for that, I'm only 33.

For those who can wear hats, I'm insanely jealous, but I doff my (imaginary) cap to you and I'll keep up the search for headwear that suits me. In the meantime, maybe I'll just have to do something else to keep my head warm as winter scampers over the horizon, like, I don't know, put the hood on my coat up or something.