What was your first big fashion purchase you made with a paycheck? Do you still wear it?
"Some years ago, I was working with stylists who helped me score my first pair of Manolo Blahniks. I keep them more now as an art installation — they are more red-carpet suited than climbing-onto-the-subway shoes."

Where do you shop for clothes?
"EVERYWHERE! Truly — I think you can find truly amazing pieces everywhere, from Target to Barneys. My favorite places to shop for the daily grind are Shopbop, Bloomingdale's, Zara."

What's your most treasured fashion item?
"At the moment, my engagement ring! I did not know that I could love a piece of jewelry with all my might!"

Jennifer's got on a Rebecca Minkoff studded leather bracelet, her father's gold watch, and beaded bracelets that were a gift.