Choosing your denim silhouette as a teenager in the early-to-mid Noughties was serious business. It marked your allegiance to a particular tribe – be it the Vans-wearing, skater-jean crowd, the Destiny’s Child wannabes with their precariously low-rise, hip-hugging fits, or the cute yet chaotic Marissa Coopers in their bootcuts. Or perhaps, like me, you went through phases of embracing each of the above in one long blur of existential angst.

So while today’s teens may never know the delights of a five-channel television, they have found themselves unearthing the joys of Noughties denim – specifically bootcut jeans. Bella Hadid has entered her bootcut-jean era, leaning into her own equestrian obsession and stepping out in a variety of Western-inspired ensembles: think bootcut jeans styled with cowboy boots, leather belts and fitted shirts.

I, for one, am convinced that I will never find the strength to return to the Y2K skinny, and I don’t think I could get away with traipsing into the offices in the raggedy, heel-trodden jeans that defined my Avril Lavigne years. But, for some reason, I feel myself being pulled back into the bootcut orbit. The question is, how am I wearing them second time around?

Shoe-wise, bootcut jeans look great with a pointed, low-heeled boot, but if you want that slouchier finish, a retro sneaker will do the job nicely. Meanwhile, when it comes to fit, I’m leaning towards a more subtle kick flare, which skims – not clings – the thigh and tapers out at the hem. While those braver than me might experiment with a hip-skimming waistband, I’ll be sticking to a high-rise fit and a cinching belt, styled with a tucked-in shirt – Hadid – or a white T-shirt and an oversized blazer. Of course, I have no doubt that Gen-Z will be going full Marissa Cooper with a layered top and a boho bag, but just like dial-up internet, that’s something I’m happy to leave behind me.

For inspiration for how to style bootcut jeans in a modern way, scroll on to discover five ways to wear the trend this autumn.

All black

A sporty spin

St. Agni

Double denin

Boho bootcut