Anna Wintour Wore a Navy Suit While Meryl Streep Chose a Red Pleated Dress for Vogue May 2026 Cover

 

Anna Wintour and Meryl Streep landing on the same Vogue cover was always going to be a moment, but the Prada connection pulls it all together. Shot by Annie Leibovitz and styled by Grace Coddington, the May 2026 issue keeps things focused: strong silhouettes, clear contrast, nothing overworked.

Meryl Streep leans into a rich red Prada look built around a flowing pleated skirt. It moves easily but still holds its shape, which gives the whole outfit a sense of control. The top half stays structured, balancing out the softness below. She adds Prada sunglasses, keeping the look sharp without adding extra noise.

Anna Wintour, as expected, keeps it precise. She wears a tailored Prada suit layered over a crisp white blouse, finished with Chanel sunglasses that immediately lock the look into her signature style. The Manolo Blahnik shoes and S.J. Phillips necklaces stay understated, but they add just enough detail if you look closely.

The styling choices are deliberate. Meryl’s look is about movement and ease. Anna’s is about structure and control. Sitting side by side, the contrast does the work without needing explanation.

Behind the scenes, the team is just as iconic. Hair for Wintour is by Bobby Michael, with makeup by Melissa Silver. Meryl’s hair and makeup are handled by Donald S McInnes, keeping her look soft but polished.

Inside the issue, their conversation with Greta Gerwig touches on everything from fashion to leadership to The Devil Wears Prada sequel. Meryl talks about shifting the character toward simplicity, while Anna reflects on experience and perspective.

It’s not overly styled, not overly explained. Just two icons, in Prada, exactly where they belong. For more from the duo, head to Vogue.com.