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.
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Available in sizes 24 to 30.
Available in sizes 23 to 31.
Available in sizes 28 to 31.
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This Is Your Last Chance to Shop the Amazon Big Spring Sale—31 Chic Finds Not to MissSo good even Levi's jeans are on sale.
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Light-Wash Jeans Always Look More Expensive When Worn With This Elevated BasicAs seen on Zendaya in Italy.
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Tired of Jeans? We Are Too—Here's What We're Wearing Instead This SpringChic and comfortable.
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7 Ways to Style Your Jeans for Spring That Feel Very 2025Courtesy of the street style set.
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My Most Complimented Everyday Jeans Are on Sale for Just a Few More HoursGrab them now, or pay full price later.
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Rich-Looking Outfits Are the Goal—31 Chic Pieces From the Amazon Big Spring Sale That Fit the BillThese will have you doing a double take.
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I Found a Trove of Cool-Girl Basics From theReplica Store Sale—31 Chic StandoutsThese have closet-staple status.
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It's Here: The 2025 Version of Skinny JeansSpotted on Emily Ratajkowski in NYC.
