Keeping Up With The Kardashians star Kim chose a very odd olive green crochet-style dress for her night out with fashion's most famous lady.
As one Instagram follower asked: "Why, Kim, why?!"
Kim, 33, and rapper fiancé Kanye were seen looking rather downcast as they headed for dinner with Anna at the Waverly Inn in New York on Tuesday (25 March).
Was Kim sad because she was cold? Because she'd only just realised her black panties were on display?
Or perhaps it was because of the backlash she's faced ever since it was announced Kim and Kanye had scored the coveted Vogue cover for April 2014.
The cover shows Kim clad in a wedding dress while Kanye stands being her nuzzling at her neck. Pictures from inside the magazine feature their baby daughter North West, born in June 2013.
But while Kim has said it's a dream come true, other Vogue fans and fashionistas have been less thrilled by it, suggesting reality star Kim hasn't earned the right to be on the prestigious cover.
However, Vogue boss Anna has defended her decision, writing in an editorial: ""Part of the pleasure of editing Vogue, one that lies in a long tradition of this magazine, is being able to feature those who define the culture at any given moment, who stir things up, whose presence in the world shapes the way it looks and influences the way we see it.
"I think we can all agree on the fact that that role is currently being played by Kim and Kanye to a T. (Or perhaps that should be to a K?)"
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Kim's best bikini moments in pictures:
Copyright: Rex Features Startraks Photo/Rex Features