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.
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Blake Lively, Sofia Richie, and More Stylish Women Know These Jeans Are Better Than DesignerThey're $98 but look way pricier.
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Fashion People Swear By Khaite's Jeans—Now I Know WhySignature silhouettes and striking details.
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Jennifer Lopez Just Wore the $98 Jeans the Internet LovesShe must've read the reviews.
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Fashion People in Paris Will Wear These 4 Elevated Basics With Jeans in 2025Easy-to-style looks.
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Sienna Miller Just Made Me Want to Wear the Jeans I Stopped Wearing Years AgoIf she wears them, they're still cool.
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Celebs in Their 50s Are Styling Jeans in an Anti-Casual Way, and I'm Here for ItDressed-up denim.
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These Are the Buzzy Color Trends Everyone Will Wear With Jeans in 2025Prepare your wardrobe.
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Stylish Women in Paris, London, and NYC Prefer These Pant Trends Over Skinny JeansVery chic alternatives.
