Anna Wintour Wore a Surprising Drop-Waist Dress to Wimbledon

published 12 July 2025

Anna Wintour wore a drop-waist dress at Wimbledon with Tom Ford

Anna Wintour's style is nothing if not consistent. She's worn the same variation of her uniform for decades—always topped with her sharply cut bob hairstyle and oversize sunglasses, of course. Her favorite thing to wear is a midi or maxi dress in a colorful floral pattern. If the weather is warm, she'll wear the dress with strappy heeled sandals by Manolo Blahnik. Otherwise, you can reliably find her in tall boots and a trench coat.

At first glance, her newest Wimbledon outfit seems to follow this formula to a T. However, upon closer inspection, you'll notice that it's actually quite a departure for her because of the drop-waist silhouette. Wintour's dresses are usually nipped in at the waist or have a column-like shape—drop-waist styles haven't been in her repertoire until now. Scroll down to see what she wore to watch the 2025 men's semifinal matches with Tom Ford at Wimbledon today.

Anna Wintour's New Drop-Waist Silhouette

On Anna Wintour: Thom Browne dress; Manolo Blahnik shoes

Anna Wintour wore a drop-waist dress to Wimbledon in July 2025

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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.