I used to want to be the man in the fedora. This was entirely due to my love of Raymond Chandler, whose whiskey-preserved protagonist was portrayed on screen by Humphrey Bogart in “The Big Sleep” (his success with Lauren Bacall only added to my hero-worship). About a decade ago, I finally bought a Borsalino in grey rabbit felt. It looked beautiful. It reminded me of the way that the brim of Bogart’s hat dropped over his right eye as he drawled bons mots between each drag on a filterless cigarette. After extensive experimentation in front of the mirror to find the perfect jaunty angle, I wore my Borsalino for the first time. Striding through the door into a work event, I caught the eye of a friend, who nudged the guy next to him. They both burst out laughing.

I never wore the fedora again. My friend’s scorn destroyed it more effectively than a boot through the crown. I’d been exposed for a mortal sin: pretentiousness. If only I’d spent more long, solitary nights with just a bottle of brandy and sheaf of cold cases for company. I thought my hat offered me a shortcut to becoming the kind of person I wished I were. But my friends saw right through it to the real me.

These days, though, I don’t feel any prickling of self-consciousness. Years watching the world of fashion have taught me that ridicule, far from being avoided, ought to be embraced. Most people choose their clothes to fit in. Standing out can be far more satisfying.

Many fashionistas get up each morning and put on something even more outré than the day before. I dress like a freak only occasionally. But when I do, I don’t hold back. I went to a masked ball in Venice wearing a hot-dog costume, and relished all those masked eyes turning to me. I strutted around my neighbourhood at the height of summer wearing a pair of Phillip Lim boxing trunks in fluoro-green-and-pink leopard print. And I have a black, grunge-luxe, floor-length Bottega Veneta sheepskin that, on a winter’s night, makes me feel like a rockstar amid the crowds of conformists in North Face nylon. Had I not lost my fedora a long time ago, I might wear that today as well.

Too much conformity can erase your character as much as pretending to be someone you’re not. Covering fashion has expanded my sense of self, by encouraging me to confront my insecurities and learn to feel comfortable with them. Off-the-wall costume is liberating: only people with cramped and unimaginative sensibilities will gawk and scoff, I tell myself.

The fashion world has embraced pretension, often labelling it “creativity”, not because the results are always beautiful, but because they show that their wearer is unafraid of experimentation. The industry lives and dies by its embrace of the new, strange and often unwearable. Without pretension it would be broke – literally. For who would buy new items to show off each season if last year’s uniform would do just as well?

Loosening up enough to wear clothes with imagination – rather than as imitation – can be a fun, life-enhancing exercise. Everyone should dress pretentiously once in while. Now, where did you get that hat?•

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