1) How did you find Alexandra?
Lily: My mom and I scouted Alexandra outside of the movie theater on 2nd avenue and 13th street, while we were taking a stroll in the East Village after a long day of work. She stood out in all black, with red lips and her boy-ish haircut-- very Edith Head (who designed for Audrey Hepburn and who Alexandra admires). Coincidentally, Alexandra has been a fan of the site ever since one of her best childhood friends, Scout Willis, was featured.

2) What did Alexandra inspire you to buy?
Lily: Red lipstick, worn Cole Haan tassle loafers and paintings by Maira Kalman.

3) What is the first thing that you remember from your shoot with Alexandra?
Lily: Her self-deprecation and her willingness to put herself in vulnerable/awkward situations like when she spotted Vivienne Westwood on a train while she was living in London, which was her first "starstuck" moment after being a tad jaded because of living in LA. Though she fantasized about merely tapping Vivienne on the shoulder and having a conversation, she grabbed her leg and started screaming at her about how much she loved her work, and then, mortified, proceeded to run off of the train.

4) What's your favorite thing about Alexandra's style?
Lily: How timeless she looks, like an old movie star, even in something as contemporary as her shaggy Top Shop sweater. Also, how willing she is to forgo all-man pleasing choices, like chopping off her hair, in exchange for the inner satisfaction of not conforming.

5) What style tip did you personally take away from your interview with Alexandra?
Lily: That sometimes, it is good to keep clothing around, even if you don't wear it for years, as you never know when or how it will work into your style or mood, as with Alexandra's thrifted Chinese embroidered top that her mother gave her when she was 13, which she initially hated, but now, 9 years later, wears all the time. Also, Alexandra reminded me that black always looks amazing and that digging through thrift stores can prove worthwhile, as it did when Alexandra found her amazing Victor and Rolf pants from Beacon's Closet.

6) What has emotionally stayed with you since your interview with Alexandra?
Lily: That honesty is the most alluring quality. I love when Alexandra says that she doesn't like hip hop because she is too Waspy and can't dance.

Questions answered by Lily Mandelbaum, Co-Founder & Editor in Chief.