6 Rare Times Anna Wintour Wore Jeans
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

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.
-
I'm a Senior Shopping Editor—29 Pieces I'm Eyeing Ahead of Black Friday That Will Get You Envious Stares and ComplimentsThese are guaranteed to elevate your wardrobe.
-
If Chic Sweater-and-Jeans Outfits Are the Goal, Don't Miss These Standout Picks From Zara, Madewell, J.Crew, and NordstromHere's to a stylish fall and winter.
-
6 Anti-Trend Shoes Experienced Shoppers Are Wearing With JeansYou can't go wrong with the classics.
-
Want to Wear Dark-Wash Jeans the 2025 Way? Style Them Exclusively With This Rich Color TrendThe chicest shade pairing for fall.
-
If You Have Good Taste, These 8 Chic Editor-Approved Fall Trends Will Be No SurpriseSee what made the list.
-
If You're as Against Wearing Sneakers With Jeans as I Am, Trust Me—This Outfit Will Change Your MindSpotted on Jennifer Lawrence in NYC.
-
Chicer Than Jeans and a T-Shirt—Everyone With Rich Taste Will Wear These Denim Outfits This FallYour new uniform to elevate your style.
-
Not Slippers, Not Boots—These New Uggs Are Already Replacing Every L.A. It Girl's Favorite SneakersThey're $150 and they're yours.

