In what can only be described as a “multiverse-collapsing” moment for the fashion world, Meryl Streep and Anna Wintour haven’t just been crossing paths they’ve been taking over the May 2026 issue of Vogue together.
For DLifestyleMagazine.com, this isn’t just a press op; it’s a full-circle legacy moment. Seeing the woman who inspired Miranda Priestly laughing alongside the woman who immortalized her is the ultimate “meta” luxury.
1. The Groundbreaking Vogue Cover
History was made this week as Anna Wintour appeared on her first-ever Vogue cover, and she chose Meryl Streep as her co-star. Shot by Annie Leibovitz, the cover features the two legends looking remarkably at ease, signaling that the “icy” reputation of the past has thawed into a genuine, high-power friendship.
2. “Streep’s Day Out” in Milan & Tokyo
While the Vogue cover is the formal news, the real fun has been the “candid” moments.
- The Milan Meet: During filming for The Devil Wears Prada 2 at the Dolce & Gabbana show, Meryl (fully in character as Miranda Priestly) met Anna front-row.
- The “Hell of a Time”: Eyewitnesses and social media clips have shown the two whispering and giggling like school friends. Anna was even seen hugging Meryl—a gesture that would make the fictional Miranda Priestly shudder, but one that proves these two are currently having a blast leaning into their shared history.
3. Inside the Conversation: Fashion & Family
In their joint interview with Greta Gerwig, Meryl and Anna got surprisingly personal about the “weight” of their respective careers.
- Meryl on Miranda: “Everybody was afraid of Anna on the first one… but with this sequel, I’m interested in the business part of it—carrying the weight of so many people’s jobs while an industry is disintegrating.”
- Anna on Meryl: “It’s such an honor to be played by Meryl, however distant Miranda is from myself. Who wouldn’t think that wasn’t the most extraordinary gift?”
4. The Style Duel: Red vs. Cerulean
The press tour has become a visual chess match:
- The Red Power Suit: Meryl’s recent “day out” featured a bold red Chanel ensemble, a color Anna has famously championed for years.
- The Glasses: Both icons have kept their signature sunglasses firmly in place during public appearances, creating a “who’s who” guessing game for the paparazzi in Tokyo and Milan.
