I first wore a pair of 501s in 1988. My brother was floundering through post-New Romantic, pre-Madchester fashion purgatory and had begun to dabble in “loon pants”, more commonly known as baggies. I was thrilled to relieve him of his old Levi’s. As a 12-year-old Brosette, this was fashion gold. They were authentically faded and blessed with the beginnings of a tear on the knee. One Saturday, I spent the whole of Going Live! agitating the tear with a pumice stone, carefully removing the blue top weave to expose a lattice of white threads below. I styled them with a knock-off Red or Dead T-shirt, a red denim jacket from the Kays catalogue and Grolsch beer bottle tops on my Dolcis school shoes. It sounds quite a lot cooler than it looked.

There were two rival factions of Brosettes at my school, and having the right jeans was a big part of winning at Bros. My dad drove me to London so that I could write 

on the door of CBS Records and go to American Classics on the King’s Road. For a denimhead, it’s not just the jeans you wear but where you buy them that counts and American Classics plays more than a cameo in the cultural history of Levi’s. It was a full-on shopping mecca, the vintage denim destination. In all the times I went, I never dared try on a pair of jeans but I did persuade my dad to buy me a T-shirt just to get the iconic bubblegum-pink carrier bag, the school swimming kit bag of dreams. 

Famous customers in the early days included Nick Kamen, the unbearably beautiful model who stripped off in the iconic Levi’s “launderette” ad in 1985, and of course Bros. “Launderette” is the standout in a run of wilfully sexy Levi’s ads, which indulged an idealised, all-American 1950s aesthetic overlaid with gorgeous soul soundtracks. But the one that left the biggest impression on me came much later. During the ad break in Coronation Street, on the portable telly in my best friend’s bedroom in halls of residence, a pearlised siren-like woman, with a heavy dark fringe, tiny silver bikini top and provocatively perfect, hip-skimming dark blue 501s stepped out of a spaceship to the opening chords of Babylon Zoo’s ‘Spaceman’. Honestly, I don’t think I’ve ever quite recovered. 501s cost £49.99 in 1995, way outside my student budget, but I bought some anyway and the jacket to match.

So yes, I did own a pair of Levi’s and the classic Trucker jacket (two sizes smaller for the required mod-esque slim fit) and I did wear them together on occasion. My first boyfriend routinely wore double denim because he was obsessed with Bruce Springsteen. The Boss is the all-time winner of double-denim Who Wore It Best, although B*Witched gave him a run for his money in the ’90s. Maybe it isn’t a coincidence that my partner is no stranger to double-denim. She has been known to try triple-denim, but I know that is just plain wrong.

I am a jeans enthusiast, not a Levi’s purist. My very first pair weren’t Levi’s. They weren’t even blue. They were black, slim fit, slightly half-mast with a button fly and – get this – tiny, silver embroidered stars all over them. I got them in York Benetton at Christmas, 1986. I wore them with a fuchsia pink lambswool jumper to the school Christmas party and drew appreciative, envious looks from the cool girls. This is the power of The Right Jeans and why it is my life’s quest to find an adult-sized pair exactly like those awesome Benetton party pants.

True denimheads scour the internet for second-hand classics, but since my brother’s 501s I have barely dabbled in pre-loved. Vintage denim is cruel – almost always the perfect colour but rarely the right shape and never the right size. The exception that proves this rule was a pair of vintage bell-bottom Wranglers with which I had a short but exciting affair during my arty phase in the early Noughties. I got them from the legendary and much-missed vintage clothing boutique Steinberg and Tolkien on the King’s Road when I was a size 10 with a “directional” haircut. Right after giving a board presentation to colleagues in magazine publishing in the basement of the now-defunct Adam Street private members’ club, the deputy editor put her hand up and said: “I haven’t been able to concentrate on anything you said because I’ve been completely mesmerised by your jeans.” All of which was normal for the Noughties, I suppose.

Ordinary people don’t understand that it is possible, and I would argue emotionally legitimate, to miss a pair of jeans. I have worn jeans almost every day for the last 35 years and at, say, four pairs a year that’s 140 pairs at least; the vast majority long lost, and in some cases best forgotten, to the great jumble sale in the sky. But the special pairs, the stalwarts, the well-washed and well-worn ones deserve remembering. My best friend still reminisces about her denim patchwork flares that saw her through the Stone Roses live in Ireland, both of our 21st birthdays and her hen do. 

Letting go of a favourite pair is difficult, and I have been known to hold on too long. My first ever designer jeans were DKNY, bought for an eye-watering £89 from Harvey Nichols in Leeds around 2000. They had a low waist, wide leg and a heavy extra seam across the knees. I wore them often with a mint green, velour sweatshirt from the lamentably short-lived boutique Uth on Floral Street and white leather Jack Purcell trainers. I wore them and wore them until one fateful morning around 2002 when my then flatmate, watching me make toast in our shared house in Clapham, said: “You do know the arse in those jeans has completely gone, right?” Devastating.

The most expensive pair of jeans I’ve ever owned were by Paper Denim & Cloth, bought from the “denim room” at Selfridges in 2005. They were slim, low on the hips and had perfectly faded “cat’s whiskers” around the front pockets. Made from the lightest cotton denim, almost silky to the touch, I wore them with a Topshop vest top and white Converse high tops. I was earning more money than I deserved working in women’s magazines, but knew deep down that paying £200 for a pair of jeans was ludicrous.

I’d just bought my first flat, a shabby, tiny one-bed on the Hackney Road, which turned out to be an unliveable nightmare due to relentless road noise and what must have been a clog-dancing upstairs neighbour. In desperation I put it back on the market after just six months, knowing that my only chance of selling it was to distract prospective buyers from the din with hipster styling details. Ten viewings led to no offers – unheard of in the market at the time, especially in this part of town. Then I had a brainwave. I hung my precious jeans over the bedroom door taking care to make sure the subtle label was showing, to indicate that this flat was the kind of flat where people who think nothing of buying £200 designer jeans live. The very next viewer offered £10k over the asking price, which is a 4,900 per cent return on investment on the jeans. Not bad. 

By now, east London had begun losing its mind in an exhausting competition between self-consciousness and overconfidence, all of which was absolutely brilliant news for my denim obsession. The new place to shop was the impressively intimidating Start on Rivington Street, which curated its denim collection from understated and overpriced statement-non-statement brands like Acne and A.P.C. 

I spent many happy afternoons there, but little money. Maybe I’d run out of ideas, or maybe I could sense that something big was coming; something that would rip my denim world at the seams. Towards the end of the Noughties, around the time that people in Shoreditch started talking earnestly about “selvedge”, came the Rise of the Skinnies. And just like that, my denim mojo left me. 

As with all trends, skinny jeans came from nowhere and, not unlike the current government, none of us thought their power could endure so long given the damage they were doing. Skinnies reigned supreme from the mid-Noughties right until 2020. During this time I got progressively fatter and poorer and was compelled to experiment with cheaper, non-branded jeans from Zara and H&M – typically low-waisted, sometimes even overdyed, with a zip fly and added stretch, all for well under 30 quid. Everyone wore them with Adidas Stan Smiths and a parka, that was the rule. That a garment which leaves you chilly around the middle and perpetually needs to be hitched up could enjoy well over a decade of unimpinged, intergenerational desirability is fashion’s peculiar torture.

Just when it seemed things could not get any worse, skinny jeans begat the aberration that is “jeggings”, which no right-minded individual would countenance. Mercifully, the scourge of jeggings has been all but driven from our nation’s stores, but it still thrives in pockets, noticeably the childrenswear department of Primark.

It took a national lockdown for us to finally ditch skinnies for good, not least because after a year in jogging pants and pyjamas nobody could get them back on. Women across the country were encouraged to try “boyfriend” and“mom” jeans instead. Boyfriend means straight but scruffy and mom means comfy, high-waisted but loose around the thigh. Hallelujah. Finally. 

But herein lies a problem. The labelling of mom and boyfriend jeans is supposedly an in-joke between the fashion editors and us customers, but I cannot help wondering what is anti-feminine and transgressive about wanting trousers that don’t give you thrush? Or why jeans that you can comfortably eat a Christmas dinner in are suitable only for your mum?

If clothes were music, jeans would be middle C.

Start with jeans and you can go almost anywhere. They can be an aesthetically neutral foundation garment or a grand statement of intent and identity. Like music, fashion is a language with its own grammar and syntax. Even confirmed anti-fashionistas unconsciously interpret signs in others’ outfits, and consciously construct their own. Styles of jeans have absorbed so much meaning that they punctuate the story of western popular culture since the 1950s. Even the least denim-literate people would understand the youthful potency of James Dean’s jeans, the angry rebellion of bleached, punk drainpipes and let-it-allhang-out hippy bell-bottoms. It is grimly inevitable therefore that jeans have ended up on the front line of today’s so-called generation wars.

Skinny jeans are now the epitome of “cheugy”, a word coined by Generation Z to shame their older millennial sisters for their fashion choices. I am Generation X and, however flattering they may be with forgiving stretch panels and a higher waistline, just cannot bring myself to buy a pair of Not Your Daughter’s Jeans, designed for baby boomers and sold in John Lewis for £139 a pop. 

However far I may have fallen from my heady days of Diesel, Evisu and 7 For All Mankind, my love of jeans will endure. My current portfolio includes blue Levi’s 724s, black Levi’s 724s and a pair of mom jeans (from White Stuff, embarrassingly) that I prefer to call my “weekend” jeans. I wear them with a pair of knackered old Nike Internationalists and a long black puffer coat from Cos. I know they make me look like a Weeble but they’re perfect for walking around a field eating a whole bag of Kettle Chips. Don’t judge me.

Liz Moseley is an editor and partner at Tortoise.

This piece was first published in the latest edition of Tortoise Quarterly, our short book of long stories. Pick up a physical copy in our shop at a special member price.

Photographs Getty Images