PHOTOS: 7 Of Anna Wintour’s Most Embarrasing Outfits

Yesterday, an image of Anna Wintour wearing what appears to be a Rockettes-in-Space costume made of latex and turquoise suede took the Internet by storm. Was is possible? Had the editor in chief of fashion’s most powerful glossy actually made such a sartorial misstep?

Once we realized even Devils in Prada wilt under the intense scrutiny of hindsight, the search was on. There had to be more of these mysterious moments, wherein Wintour wore things that would not look out of place in Romy and Michelle’s High School Reunion. To our shock, there were more. Many more. So many more that we pulled seven of our favorites — bookended, of course, by Anna at her earliest and her most recent — and posted them below. Laugh, enjoy, and feel better about that time you wore glittery teal eyeshadow, crimped hair, and JNCO jeans.


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