Cindy Crawford Has Been Wearing This '90s-Supermodel Jean Outfit For 25 Years—and It's Still Just as Elegant

By Swedan MargenNovember 18, 2025

Finding something different to wear every day of the week can be a challenge, but the good news is that there are a few foolproof outfits to wear when you're at a loss. I find myself digging through drawers and staring at the same items in my closet over and over again with that one thought we always have from time to time: I have nothing to wear. Luckily, Cindy Crawford is here to remind us of a jean outfit that has stood the test of time

While out to dinner in Beverly Hills recently, Crawford wore a leather jacket paired with jeans and brown boots. It sounds too good to be true, as it's so simple, but it’s an elegant outfit formula that will never fail you, no matter what the decade may be. Crawford would know, as she’s worn this exact outfit formula on repeat occasions since the '90s. What I love about this look is that it suits anyone with any type of style. It’s a versatile outfit that’s great for going out to dinners or meeting up with friends, and laid-back enough to give off an effortless vibe—true model-off-duty look.

If you’re on the market for a simple, but elegant outfit to wear over and over again like Crawford, keep scrolling to recreate her look and shop similar items.