The return of the trilby: the snappy look set to define our roaring 20s

Gents, what’s stopping you from dressing like you play the keyboard in a function band? It’s 2022 and you shouldn’t be worried about injecting a little pizzazz into your wardrobe. Ann Demeulemeester has done it, and so has Alessandro Michele and Raf Simons, who presented their own iterations of the trilby for AW22. Just look at the swathes of people who still go to Pitti Uomo, uploading photos of themselves on Instagram wearing colour-blocked, skinny-fit suits, hashtagged #menswear – the style set is really catching on!

Quite honestly, I have looked at lots of pictures in the process of writing this report and I still can’t tell the difference between a trilby, a pork pie, and a fedora. This is because I have a condition where my eyes actually refuse to focus when looking at images of men in jaunty little hats. But lest I inflame the trincels, the chapeau in question is generally distinguished by its shorter brim, which is turned-up and angled towards one singular eyebrow. It winks, if you will.

Unfortunately, the style acquired an unbecoming rap in the mid-2000s when young men decided to dress like TV detectives in order to appear more gentlemanly to the opposite sex. Worn with pointy brown shoes and fun socks, there was a certain chivalry to it, until their eyes clouded over whenever their target woman spoke. Emboldened by Justin Timberlake, the sexiest man of 2003 according to “a poll”, the trilby became the calling card of a deeply complex, creative soul – proliferating X Factor audition rooms and the Disney channel, alike, where the accessory gained real panache and fluidity.

Styled with string-bead necklaces and shrunken waistcoats on pop starlets – and Ryan, the gay one from High School Musical – the whole thing reached saturation point around 2011 when cheeky chappy Olly Murs was forced to retire his trademark trilby. Speaking to the Daily Star newspaper he said: “I’ve got rid of all my hats now because people kept giving me grief about them. They would come up to me and say ‘You’re the one with the hat’.” Britney Spears, Christina Aguilera, Paris Hilton, and Miley Cyrus seemingly followed in the singer’s lionhearted footsteps.

Ten years later, the style has found a nesting place atop the heads of men’s rights activists and amateur poets (the kind who like to stroke their chins in photos). Early internet women didn’t know how well they had it, lampooning these chaps in blogs like the now-defunct Fedoras of OkCupid. “Omg what is it with these guys calling themselves ‘gentlemen’ or ‘classy’ because they own a fedora?” wrote one of these ladies. “I can smell the benevolent sexism from here,” she said, not realising that she was probably speaking to a smooth, timeless blues troubadour.

Of course, the hat itself has no intrinsic value – and much like every other vestige of the Y2K-meets-Indie Sleaze era, it’s ripe for reimagining. If UGG boots can make a comeback on the hooves of East London It-girls then surely the trilby can smooth talk its way back into public consciousness. Zendaya’s look for the Vanity Fair Oscars party, a sinuous trouser suit with a PURPLE shirt and a GLOSSY tie was practically begging for a crooner’s cap.

All this is to say: Julia Fox NEEDS a trilby. M’lady NEEDS to cock her hip and pinch the rim of a tiny little hat.