Last night I was just about to shut my laptop when my husband said “Rach! You have to get in here – Anna Wintour is on Letterman.” Now, I don’t know that I’ve ever heard Anna Wintour speak for more than five seconds so this was of course serendipitous timing since my other work just happened to be done. I quickly went into the living room and settled in to see what this kind of interview would be like. Was I worried that she would be dry? Yes. Did I wonder if he might offend? Oh, absolutely. But what we ended up with was a very sweet interview that was both funny and insightful into Wintour’s personality. I decided the best way to present what I liked best about the interview was, naturally, to make a list.


Image: Newscom

The humor. She was funny! I know it might seem a tad offensive to be so surprised by this, but wow Anna Wintour has a sense of humor. I would have never guessed this.

The dress. I am so very much in love with the black and white dress she wore. It was far less of a surprise to see her wearing something so truly covet-worthy.

The self reflection. You can tell she is very aware of the way she is depicted by the media and doesn’t take it all too seriously. I imagine you would have to once you have made it that far.

The passion. She so very clearly loves what she does. When she started talking about ‘The September Issue’ and the work that goes into that landmark issue, you could see her soften a bit – I would have guessed that she must care a great deal to do what she does, but it was heartening to see that on TV.

The insight. I will be going to see ‘The September Issue’ the day it comes out. Every little tidbit that sneaks out about what it is like to work in that office and be a part of that magic is (silly as it might sound) captivating.

The references. After so much press and speculation about the way in which her character (supposedly) was depicted in ‘The Devil Wears Prada’, it was neat to see her take it in stride and have fun with the topic instead of clamming up or getting offended.

The socks. Oh that early comment about Letterman’s socks was priceless. Can you imagine Anna Wintour commenting on something you are wearing? Like him, I’m sure you would wonder if she really did approve or the remark was in jest.