Until my early 20s, the shape of my legs was one of the world’s great mysteries. Twigs or tree trunks: it was anybody’s guess. I spent my waking life in loose-fit, skater-inspired denim, slung low, and usually frayed and revoltingly filthy at the hem. These jeans were my message to the world: Forget it — I’m not dressing up for you. Things changed drastically in early 2006. I remember picking up my first skinny jeans in Urban Outfitters, eyeing them with the wary curiosity of somebody being served snails for the first time. They seemed so unforgiving, so peculiar, so very different from what I considered to be “jeans.” And yet, within a few moments of maneuvering myself into them, I was head-over-heels in love. I spent the next several months being told, "You've lost so much weight!" — but I had not. It was just that, suddenly, people could see my actual figure. Moving to London that year with my degree, a brand-new hairstyle, and my freshly unveiled limbs, I felt like a modern Melanie Griffith in Working Girl. The last decade, for me, has played out against a glorious spectrum of skinnies. There were gray, Kate Moss-homage jeans in 2007, so obscenely tight that a colleague told me I had to stop wearing them. There was a red J Brand pair in 2011, which seemed to go out of fashion about five days after I bought it, swiftly followed by an animal-print pair in 2012, cropped to a length that made me look like I’d just had a growth spurt. There were dozens of pairs of blue jeggings, all of which would begin to pull apart at the seams after a month or two, and there were the great-with-anything black skinnies that became my uniform for 2015. But drainpipe-devotee that I am, I’m also a journalist who writes about fashion. Those tight, tight jeans may have limited the blood supply to my brain — but they haven’t been enough to distract me from the news that skinnies are no longer “cool.” According to a study by WGSN, there were 93% more wide-leg jeans on the spring 2016 runways compared to the previous spring. Skinny jeans had dropped off by about 3%. Not a catastrophe, but when you turn to street style, the plot thickens: Editors and other fashion-forward types have long since moved on to other kinds of denim, be they flares, culottes, mom jeans, or boyfriend cuts. The skinny jean — and I say this as someone who still has eight pairs hanging in her closet — has tipped into the passé.
I don’t want to become the middle-aged lady who insists on wearing what was fashionable when she was 22. Being unadventurous is bad for the soul. So a week ago, I frog-marched myself into Whistles and tried on its light-wash boyfriend jeans. I trotted out to where my roommate was waiting; she glanced up from her phone, did a double take, and completely lost her composure. “You look like your mum in the '90s!” she choked out eventually, wiping away tears. In fact, the mirror revealed, I looked more like my father circa now, in his jeans that are two sizes too big for him and at least two decades old (because “Why would I throw them away when there’s nothing wrong with them?”). The loose-fit, pale-rinse denim, to my skinny-trained eye looked unshapely, unstylish, and worst of all, unflattering. The store assistant weighed in helpfully. “It just takes time to get used to them,” she said. “When customers first try them on, they often say, ‘I look like a boy.’” I reluctantly gave her the jeans to pack up and I took them home.
The next day, I was due to visit a designer at her studio, so I gave them a try. I wore them with a shirt and navy sweater, my chunky watch, and Stan Smiths, and I rolled up the hems for a more contemporary shape. It’s the kind of look that would mystify my parents ("Are you going paddling in the sea?" they would probably ask, after a long pause). It was a frosty day in February, so my bare ankles weren't thrilled, either. Because this is fashion — an industry where you could turn up for lunch in a body stocking and your companions would only yawn — the designer and her staff did not notice my jeans. The only one who did was the studio dog, who made a beeline for me and spent the next 20 minutes furiously and thoroughly licking my ankles. On Day Two, I googled “ways to wear boyfriend jeans,” only to be confronted with dozens of pictures of celebrities in strappy stilettos. This was categorically not happening. I am not a glitzy-footwear kind of woman, and to me, ‘dressing up’ your boyfriend jeans negates the best thing about them: their utter devotion to being relaxed. I settled for black ankle boots, which looked a little more work-ready than my sneakers. That day at a gallery, a stranger stopped me and asked if I was an artist. This made no sense, but afterwards I reflected that maybe she wouldn’t have asked me in my skinny jeans — too conformist, too pedestrian. I awarded 10 points to my denim, which I had now mentally upgraded to “intriguingly creative.” On Day Three, I wore the jeans with an enormous cashmere sweater, reaching my absolute pinnacle of casual comfort. Dressing like this reminded me of my teenage self: unformed, informal, keen to blend in. Ironically, it made the grownup me feel conspicuous. I added bright lipstick, not to stand out more but because I wanted to look more appropriate for the outside world — I didn’t want anyone to assume that I’d given up on myself. “Have you seen Hattie today?” “Yeah… Looks like she’s going through a rough patch.”
But as the days ticked by — uneventfully, with friend after friend giving the jeans a shrug — I felt the return of a kind of muscle memory, of how at ease I once was in a silhouette like this. It feels indulgent to be so relaxed all day, so poised to lounge around. I have found myself wearing them to watch TV, which has always been the cue to change out of my restrictive skinnies. And though boyfriend jeans are not form-fitting, I have remembered that they have a different kind of slouchy sexuality to them, in the way they hang off the hips. They remind me of the Levi’s Twisted Jeans that I so desperately wanted as a teenager: nonchalant and cool. Even my roommate has grown to like them. “If I were five years younger,” she told me, “I wouldn’t have found them funny.” She’s right. As a teenager, when a trend from the ‘70s would reemerge, I remember my mother cringing: “It reminds me too much of what we used to wear.” To me, those ideas were fresh — and loose-cut jeans in washed-out denim probably feel the same, if you’re young. We’re just old as dirt, and we know too much. I’m not officially giving up on my skinny jeans: I still need them for first dates, work events, and days when I feel like showing off my tree trunks. But I’ve decided I need a looser, softer pair in my life, too. In fact, I feel like I’ve rediscovered a dear old friend — and in forcing myself out of my fashion comfort zone, I’ve made myself more comfortable than I’ve been for years.