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 bootcut jeans. 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. Like many other new-gen trends, the bootcut jean’s renaissance has seemingly bypassed the runways, with Gen-Zs cutting out the middle man and delving straight into the archive, using platforms such as Pinterest to compile moodboards populated by throwback pap shots and old film references, alongside new celebrity style crushes.

Bella Hadid is one such crush who 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 Vogue 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 jean’s 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, which, together, look the part when styled with a tucked-in shirt—à la Hadid—or a white T-shirt and an oversized blazer.
Of course, I have no doubt that Gen-Z fashion plates will be going full Marissa Cooper with a layered top and a boho bag, but I think I’ll be leaving that combo to my past self who is forever immortalised in a world of disposable cameras and dial-up internet.
Polo top + faux-fur jacket + black bootcut jeans
Denim shirt + leather jacket + blue bootcut jeans
Track top + sneakers + blue bootcut jeans
Parka jacket + combat boots + bootcut jeans
This story was originally published on British Vogue.