Once a cornerstone of 1990s minimalism and early 2000s casual wardrobes, skinny jeans are making a quiet comeback in spring street style. If you're wondering which skinny jeans work best with your look, check out the fashion archives—our favorite style muses have long since shown us how to wear the skinny silhouette flawlessly.
Like a supermodel
There's probably no better source of inspiration than archival photos of celebrities at airports in the late 1990s. At Los Angeles Airport, Cindy Crawford perfected the formula for relaxed chic: skinny jeans, a classic T-shirt, a simple jacket and black ankle boots. Add large sunglasses and a bag, and you've got a look that will look good even after a long trip.
Cindy Crawford. Ron Galella, Ltd./Getty Images
Grunge zeros
If your stylistic moodboard is closer to Ginny Humphrey than Blair Waldorf, pay attention to Gisele Bündchen's looks from the early 2000s, an era when airport bars were much more popular than yoga retreats and juice detoxes. Skinny jeans, a leather jacket, a V-neck T-shirt, and biker boots create the same carefree, slightly grunge look of the zeros.
Gisele Bundchen. Photo: Marc Piasecki
Total black
Among the many style lessons Kate Moss has given us—from slip dresses to leather jackets—there's also the perfect way to wear skinny jeans. Go monochrome: black skinny jeans, a fitted jacket, heeled boots, and, of course, XXL sunglasses to help hide the effects of a stormy night.
Kate Moss. Paul Ashby/Getty Images
Y2K Aesthetics
Sienna Miller is without a doubt the style icon of the early 2000s. In 2005, the actress paired skinny jeans with ballet flats — a look that has been recreated time and time again since. An asymmetrical white top, giant sunglasses, and the era’s signature accessory — a Balenciaga Le City bag casually slung over her elbow — complete the look.
Sienna Miller. Photo: Tom Wargacki
Denim on the red sidewalk
Today's red carpets often gravitate toward a bare-bones aesthetic and maximum Hollywood glamour. But in the 1990s and early 2000s, even photo ops couldn't escape the pull of skinny jeans. At the 2004 Venice Film Festival, Angelina Jolie wore low-rise jeans, accessorized with gold pointed-toe pumps and a Louis Vuitton bag—in the best traditions of early 2000s A-list style.
Angelina Jolie. Pascal Le Segretain/Getty Images
Based on materials from vogue.co.uk