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 oversized 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.

Thom Browne dress; Manolo Blahnik shoes

Erin got her start as a Who What Wear intern over 14 years ago—back when the site only published a single story per day. (Who What Wear has since increased that number twentyfold.) She graduated magna cum laude from USC, which is how she ended up moving to Los Angeles from her hometown of San Diego. 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 currently holds the title of Associate Director of Fashion News (as well as the unofficial title of resident royal expert—in case you haven't noticed her numerous Kate and Meghan stories). She spends her days trying to incorporate her idols, Anna Wintour and Roger Federer, into as many stories as possible.