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
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