Anna Wintour at the 2025 CFDA Fashion Awards: Signature Bob, Sunglasses and a Very On-Brand Dress

Anna Wintour’s new role, same unmistakable style

In 2025, Anna Wintour made a rare move: she stepped down as editor-in-chief of Vogue, a role she had held since 1988, and shifted into a broader position as the magazine’s global editorial director.

But as The Seattle Times notes, her job title may have changed, her look has not. She continues to appear on major red carpets — including the 2025 CFDA Fashion Awards — in the uniform that has become instantly recognisable:

• Precision bob

• Oversized sunglasses

• A covered-up dress, usually printed

• A fitted jacket or coat layered over the top

It’s a visual shorthand that tells you you’re looking at Anna Wintour before you even read the caption.

The 2025 CFDA Fashion Awards: where and why it matters

The 2025 CFDA Fashion Awards were held on 3 November 2025 at the American Museum of Natural History in New York City, continuing the Council of Fashion Designers of America’s long-running tradition of honouring American and international fashion talent. On the winners’ side, the CFDA confirmed a high-profile line-up of honourees, including:

• A$AP Rocky, who received the Fashion Icon Award

• Ralph Lauren, who won Womenswear Designer of the Year 

For this edition, Wintour’s role wasn’t just as a guest. She was onstage to present the Fashion Icon Award to A$AP Rocky, a moment Vogue also highlighted in its coverage of the night.

What Anna Wintour wore to the CFDA Fashion Awards 2025

Red-carpet coverage from Marie Claire notes that Anna Wintour arrived at the American Museum of Natural History in a floral Ralph Lauren dress, a fitting choice on the night the designer took home Womenswear Designer of the Year.

That look slots neatly into the pattern outlined by The Seattle Times: an elegant, fully covered dress with print, her trademark bob, and dark sunglasses — the “signature style” she has kept for decades.

Behind the scenes, Page Six also reminded readers of a long-running CFDA in-joke: the awards dinner once again served chicken pot pie, a dish often described as Wintour’s favourite at the event. It’s a small detail, but it adds to the sense that this is one of the red carpets where she is most at home.

Why her CFDA appearance still matters

For fashion people, Anna Wintour attending the CFDA Awards in “uniform” does a few things at once:

• It signals continuity: even after stepping down as Vogue’s editor-in-chief, she remains visible at one of American fashion’s key industry nights.

• It underlines her role as a power broker, not just an editor — presenting the Fashion Icon Award to A$AP Rocky, a musician whose influence crosses music, streetwear and luxury.

• It reinforces the idea that personal style can become a kind of logo: the bob, the sunglasses, the printed dress and jacket functioning almost like a brand identity on the red carpet.

For readers of Niche Magazine UK, the takeaway is simple:even as titles and job descriptions shift, Anna Wintour’s presence and silhouette at major fashion events still hold symbolic weight — and the 2025 CFDA Fashion Awards were another reminder of how tightly controlled, and instantly legible, that image really is.