Anna Wintour is a creature of habit when it comes to her signature style. She wears the same shoe brand over and over. She relies on different versions of the printed midi dress nearly every day. She's not afraid of wearing the same boots with a dozen outfits. Given her predictable uniform, you might think you have her style down pat—but she'll throw you for a loop when you see these throwback looks.
As it turns out, the impeccably dressed Vogue EIC does own jeans like the rest of us mere mortals, but she has only been photographed in them on rare occasions. I did some digging to find every time she's stepped out in public wearing jeans and came up with these six excellent looks. Scroll down to take a walk down memory lane.
Shop Bootcut Jeans
Available in sizes 24 to 30.
Available in sizes 23 to 31.
Available in sizes 28 to 31.
-
I Found a Trove of Cool-Girl Basics From the Nordstrom Sale—31 Chic StandoutsThese have closet-staple status.
-
It's Here: The 2025 Version of Skinny JeansSpotted on Emily Ratajkowski in NYC.
-
35 Incredibly Chic Luxury Finds I Would Immediately Buy If My Salary Tripled TomorrowA girl can dream, right?
-
I Own $500 Jeans, But This Under-$150 Pair Looks and Feels More ExpensiveTrust me.
-
I Tried This Curve-Friendly Denim Brand for the First Time—These Are the Jeans I'm Wearing NowEverything you need to know about popular Good American denim styles.
-
Anti–Skinny Jeans Are Still Ruling in 2025—Finally, 15 Fresh Ways to Wear ThemStealing these looks this season.
-
These 5 Inspiring Outfits Are Proof You Can Easily Merge Classic and Trendy StylesTrust me, you're going to want to re-create these looks.
-
The 2025 It Girl's Wardrobe: 9 Highly Specific Brands and Buys They're All WearingFrom handbags to jeans to jewelry.
