It was Anna Wintour’s 70th birthday yesterday. Page Six did a whole thing on what an enigma she still is and whether or not she really is as mean as she’s reputed to be and what her life is really like. Someone said she’s “Machiavellian”. Someone else says she’s misunderstood, that she’s actually “shy, kind, loyal, a great friend, fiercely intelligent and cultured beyond belief”. 

Buried in all of this, however, is the rumour: 

“There have been rumors that the editor is involved with British actor Bill Nighy — “kind of a Shelby look-alike,” said the Wintour source — with the two spotted together at plays in New York and London.”

Shelby would be Shelby Bryan, Anna’s husband, who is rarely seen with her, especially not the last few years after his tax problems in 2013, around the time speculation began that she and Bill Nighy are together. Here, play Photo Assumption on this shot from 2012 at a fashion show in London: 


Anna does smile…but her smiles aren’t always warm. This is a WARM smile. 

So how legit is this? Last year Anna and Bill were seen at the theatre together, twice, but he insisted that they’re just friends. I don’t know that we’ll ever really know, but I do like the idea of it. I like the idea of Anna Wintour having some fun with Bill Nighy, aka Billy Mack, the movie character who’s especially popular this time of year, the time of year we all either watch Love Actually or yell about how Love Actually is reductive and derivative. 

No matter how you feel about the movie, or how your feelings about the movie have evolved, we can still all agree that he’s funny at the start of the movie when he’s recording the song, in that ridiculous but perfect shirt, doing his ridiculous but perfect squat. I know he’s just acting, but wouldn’t you kinda want to see how this works with Anna Wintour?