JASON WU Age: 27. Designed Michelle Obama's inauguration gown and dresses celebs like Katie Holmes.
DIANE VON FURSTENBERG Age: 62. Revolutionized women's wear in the '70s with her wrap dress; president of the Council of Fashion Designers of America.
You've each had some big career moments. Which was most memorable?
VON FURSTENBERG: When I was on the cover of Newsweek at the age of 28. That changed everything—overnight, everyone knew who I was. And it's like, I was the same person as a week before, but people looked at me differently.
WU: For me, it was seeing my work on the First Lady on Inauguration Day. My mom called five minutes after that happened, and she goes, "Well, I finally understand what you do!"
Are you trying to make history when you design?
VON FURSTENBERG: Do you think when I created that stupid wrap dress I thought it was going to be with me for the rest of my life? You just do what you think is right.
WU: I look back a year ago and it's like, I knew so little!
VON FURSTENBERG: And I have such a long time in the industry, and I'm still learning.
What have been your biggest challenges?
WU: My first year, a store I sold to went out of business, and I was stuck with an entire collection. It's scary. But it's about climbing back up.
VON FURSTENBERG: I had sold my company [in 1978] and I came back in the '90s. And I tried to do it again and people looked at me as a has-been. They had no faith in me—but I came back.
Is there anything you won't wear?
VON FURSTENBERG: I don't like white shoes.
WU: Well, I'm wearing white shoes today!
VON FURSTENBERG: There are also clothes I design that I can't wear now, because they're for women much younger than I am. But I love jersey, because it allows you to move.
WU: Jeans and Converse: That's my uniform.
What do you think of shows about the industry, like Project Runway?
VON FURSTENBERG: I like that it shows the process, but I don't like how it always shows the negatives. I hate that.
WU: It's a show, so it's dramatic! But designers don't fight with each other. We're too busy working to be catty and sabotaging other people.
Where do you find inspiration?
WU: I was shopping in the East Village earlier and ideas just hit. I'm always working, 24 hours a day.
VON FURSTENBERG: Me too! Wherever I am, I keep a diary with my camera. Maybe I'll see a stone on top of a mountain and find a way to use it.
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