Anna Wintour showed us how to wear boyfriend jeans back in 1988, when she put a model wearing a pair on her first ever American Vogue cover. The image of Israeli Michaela Bercu in stone-washed Guess denim with beaded Christian Lacroix jacket rocked the fashion world. Jeans, on a cover? With couture? “This one broke all the rules,” the enigmatic editor-in-chief later said.
“It was so unlike the studied and elegant close-ups that were typical of Vogue’s covers back then, with tonnes of make-up and major jewellery.”
Just like their American Vogue cover debut, boyfriend jeans – and denim in general – have always shaken up the status quo. They were made popular by James Dean in 1955 cult classic Rebel Without a Cause, after which they became the sartorial symbol of the decade’s youth rebellion. But it wasn’t until the 60s that jeans were considered acceptable for women, and that was only after icons like Marilyn Monroe took to wearing the baggy boyfriend style between takes on set.
The key to making this look your own is how you wear them — never let anyone tell you that wearing boyfriend jeans can’t be just as sophisticated as wearing skinnies. If your relationship status with the slouchy style is complicated, consider this the couple counselling you and your denim need.
Borrowed from the boys
Menswear has informed women’s collections since Coco Chanel’s famously androgynous aesthetic made waves in the 1920s. What girl doesn’t love an oversized men’s shirt tucked into a suede mini, or YSL’s iconic Le Smoking tuxedo vamped up with a vermillion lip? Now that blurring gender lines in fashion is de rigueur once more, it’s no surprise that boyfriend jeans are back.
Much has been written about pulling off boyfriend jeans by prettying them up, but don’t be afraid to embrace their masculinity by pairing them with Nicholas Kirkwood patent loafers and a crisp men’s striped shirt. Pulled together with a structured military-style blazer on the shoulders and hair scraped into a low chignon, the effect is polished but not remotely prissy.
Consider wearing boyfriend jeans with sneakers (think Adidas, Converse or Lacoste) to play up their tomboy vibe. A graphic Kenzo knit or colour-blocked top taps into the athleisure trend and sharpens up a slouchy silhouette.
Opposites attract
When Katie Holmes stepped out on the streets of New York wearing what appeared to be then-husband Tom Cruise’s denim in 2009, she unwittingly gave the world a lesson in how to wear boyfriend jeans (and showed us that, for all his faults, at least Tom Cruise had a wardrobe worth stealing from). The style came back in vogue almost overnight as women took note of how Holmes balanced the baggy bottoms with a closer-fitting top — the ideal approach to avoid swamping her small frame.
One of the keys to balancing the roomy proportions of boyfriend jeans is to show a bit of ankle. Cuffing them, while no longer considered crucial (see Valentino styles), creates a tapered silhouette that’s further enhanced by a pointy-toed stiletto heel. How to pull off boyfriend jeans, without sacrificing your natural shape, is to cinch them in at the waist with a skinny leather belt — a statement buckle adds instant polish — and stick to long-line blazers or coats to conceal a potentially unflattering behind.
Even a heavily distressed pair of boyfriend jeans can be made to look elegant with girlish accents, from a silky Givenchy bomber jacket to a pop of vibrant colour care of a cross-body Saint Laurent Monogram bag. Choose boyfriend jeans with a hint of embellishment, such as floral embroidery, pearls or Valentino’s rockstuds, if you want to further accentuate their feminine side.
Find your type
Boyfriend jeans have come a long way from the simple bleached wash with ripped knees iteration. While you can’t go wrong with such a classic take on the trend, there’s now so many more styles to choose from, making it easier to determine how to wear boyfriend jeans beyond pottering around the house.
Make yours of the moment with a slightly flared fit and nod to fashion’s obsession with breezy 70s style — a slightly cropped length makes the flare a flattering counterpoint to the slouchy shape above. Rag & Bone and Citizens of Humanity realise this perfectly in their styles, which pair well with a loose-fitting linen tee and cropped leather jacket for relaxed weekend wear.
If you can’t think of anything more banal than wearing boyfriend jeans, you’re in luck. Increasingly, designers are dressing up boyfriend denim with an eclectic array of embroidered details. In the case of Alexander McQueen, this means dazzling sequinned hummingbirds flitting across the thigh. The look is directional, adventurous and light years away from the plain blue worker’s jeans Levi’s first created in 1873. Go bold, or go home.