Were there any styles or designers that you had to convince Michelle to wear? Were there any looks she was ever skeptical about?
She is pretty open-minded, in a way, and she’s also really practical. She’s not going to do something where she can’t move, she’s super uncomfortable, or she’s super hot. She’s very interested in, “What’s the weather? What’s the venue? Who’s going to be there?” My philosophy is, like, let’s see what the potential in a garment is. Even in this last photo shoot that came out, I had Jason Wu make this beautiful dress from his most recent collection, and she just didn’t feel great in it and wasn’t really open to exploring it, which made me extremely sad. So after the fitting, I took the dress and I was just thinking, How can we make this work? Because I really wanted Jason to be included in this—he’s an amazing designer, his work is solid, and the dress is beautiful. We ended up turning the dress into a top and pairing it with some sort of reconstructed jeans from Sami Miró, and she eventually got on board. But what I do is, I convince, I prepare, and then I also prepare to be disappointed.
In the book you mention that you never got attached to anything. That’s hard to do, I can imagine.
It is only because the attachment isn’t about that fashion has to be this or that. That is not necessarily how I feel. Although I do admire and really, truly respect so many houses, designers, and brands, it’s not so much about the parts of fashion that are glamorous and flashy. It’s just more about what can work for her, right? Woman to woman, I don’t want to make another person uncomfortable, especially a client. There are limits. I kind of know where I can push her and where I need to just say, “Okay, we’re just going to do what works,” because it’s more important for her to be comfortable than to be a fashion plate.

