From Cindy Crawford to Kate Moss and Angelina Jolie, here’s a look back at how they adopted the trend
Every few years, skinny jeans rise like a ghost from the not-so-distant past and sure enough, the time has come once again to dig them out of your wardrobe for another stint in the spotlight. This year, we’re leaning into nostalgia, with throwback nods to the boot tuck and all things indie sleaze.
A cornerstone of ’90s minimalism and early-2000s off-duty model dressing, the skinny silhouette has quietly re-entered the spring street-style arena. If you’re feeling hesitant, take reassurance from the past. Below, we take a look at how our favourite style muses did it first.
Off-duty supermodel
There is perhaps no more reliable style inspo than celebs at the airport circa the late ’90s. At LAX, Cindy Crawford perfected the art of off-duty chic: skinny jeans, a classic tee, a blazer on top and black ankle boots. Add oversized sunglasses and a shoulder bag and you’ve got a look that’ll hold up after any long-haul flight.
Noughties grunge
If your moodboard leans more towards little Jenny Humphrey than Blair Waldorf, take cues from Gisele Bündchen in her early-2000s era (when the airport bar took precedence over yoga retreats and juice cleanses). Skinny jeans, a leather jacket, a slouchy V-neck tee and biker boots make this the grungy, thrown-together look of the Noughties.
All-black
There are many styling lessons we can take from Kate Moss (slip dresses, leather jackets, the list goes on) but for today, we’re shining a light on this throwback skinny jeans look. Go full monochrome in black skinnies, teamed with a fitted jacket, heeled boots and, of course, XXL sunglasses for hiding from the night before.
The Y2K look
Forever a style icon of the early Noughties, Sienna Miller has earned her place in the skinny jeans history books. In 2005, the actress paired denim with ballet flats and we’ve been trying to replicate this look ever since. An asymmetric white top, giant sunglasses and, crucially, a Balenciaga Le City bag tucked into the crook of her arm complete the look.
Red-carpet denim
Although it may all be a bit more naked dressing and all-out Hollywood glamour these days, back in the ’90s and Noughties, even the step-and-repeat wasn’t immune to the pull of skinny jeans. At the Venice Film Festival in 2004, Angelina Jolie opted for low-rise skinny jeans, finished with pointed gold pumps and a Louis Vuitton bag, in true 2000s A-lister style.
