One of my all-time favorite looks from the ’90s is a pair of straight-leg blue jeans and some low-heeled boots (ideally a block heel, and a square toe). This minimalist outfit was beloved by so many actors and models of the era (case in point: Cindy Crawford, basically every time she was in an airport during that decade; Jennifer Aniston and Courteney Cox whenever they weren’t on a red carpet promoting Friends; Winona Ryder if she wasn’t in boxy suit or a silk dress). Indeed, though they all had a different styles and approaches, cigarette jeans and low heels were a uniform of sorts for these high-profile women of the ’90s.
Get the Jeans and Boots Combo:
It’s also a look we’re seeing a lot of at the moment–especially among the street-stylers and off-duty models milling around New York for fashion week, who can often be spied clutching their iPhones in a blocky boot and straight-leg jeans. The recent runways are pushing ’90s minimalism, too (it makes sense that Love Story’s Sarah Pidgeon, who plays Carolyn Bessette-Kennedy, attended Khaite’s autumn/winter 2026 show, which was all cigarette silhouettes and low-heeled boots).
While I’m more of a zero-heel girl myself, Vogue’s fashion writer Olivia Allen regularly comes to work in straight-legs and a blocky heel–usually styled with some kind of minimalist cashmere knit. “I have way too many pairs of jeans and find myself reaching for one of countless identical options in the morning,” she says. “However, I am also, a) wary of falling into the trap of looking like a Bruce Springsteen tribute act and, b) allergic to trainers. The walkable heel helps me avoid both, while also addressing any height-based insecurities. There is no greater serotonin boost than strutting down the street in a pair of boots (plus sunglasses and wired headphones).”
As winter gradually shifts to spring, I find myself increasingly convinced by this absolutely failsafe ’90s combo. I’ve always wanted my own uniform–why not one co-signed by Cindy Crawford herself?
