1) How did you find Jesse? (scouting, referral, etc?)

Lily: We found Jesse through his friend and SLU alumni, Trae Harris, whose drop dead Closet we featured on the site a couple years back. Trae is a member of Jesse’s “Romantic Movement” and is also featured as the object of Jesse’s affection in his new music video, “Before the Night is Thru,” a video packed with people whose style I am obsessed with, including Joanne Petit Frere, Dynasty & Soul, the Street Etiquette boys and many more.

2) What did Jesse inspire you to buy? Music, books, clothes, etc?

Lily: Jesse inspired me to re-visit my turquoise ring obsession and also prompted me to contact Dynasty Ogun (featured a couple months ago on the site), whose custom-made floral shirt Jesse wears in his interview. Now I have a pair of Brze’s drop-crotch army pants on the way which I am very excited about :). Also he made me want to read Joyce and Whitman.

3) What's the first thing you remember from your shoot with Jesse?

Lily: Dying over Jesse’s hair.

4) At what point during this shoot did your jaw drop to the floor? Why?

Lily: When Jesse gave us a taste of the spoken word poetry by his performance alter ego, Bartholomew Jenkins, who Jesse says is the “smooth” and “rugged” version of himself (see 3min40 seconds in the video). Not only am I in awe of anyone who has the courage to expose their fragility through poetry, but I also admire how Jesse openly speaks of coping with his vulnerability by channeling his nervous energy into this character. Plus, the lyrics are beyond sexy and beautiful. Ramona and I basically melted to the ground at this moment in the interview.

5) What is your favorite thing about Jesse's style?

Lily: I love the way that Jesse combines prints --from African Kente cloths to rich florals -- with more subdued, classic pieces. Being a huge fan of prints and all things ethnic without wanting to look over the top, I am always looking for ways to mix and match simple and loud pieces, a quality that I think Jesse has mastered.

6) Who else on StyleLikeU does Jesse remind you of? Why?

Lily: Jesse’s style reminds me of Preston Davis and Nick Fouquet. Jesse also reminds me of Nacinomod Deodee in his spirituality and artistry.

7) Emotionally, what has stayed with you since your interview with Jesse?

Lily: What Jesse says about balancing “the world” in one hand and “his heart” in the other hand. He's completely dedicated to delivering his art with a strong social message about respect for women to his listeners, but knows that he can’t be a total purist if he wants to succeed in the real world, a path to which I relate with StyleLikeU. Being someone who functions both practically and from a place of passion, I understand Jesse’s struggle and desire to equally balance the integrity of his artistic pursuits -- “his heart”-- with the reality of living in today’s fast paced, competitive and often shallow society-- “the world”.

8) What was the most covetable item in Jesse’s wardrobe?

Lily: His Brze shirt and his custom made Nike leather jacket.

9) Did Jesse remind you of a song, painting, or film?

Lily: A few weeks ago, when I saw the Bob Marley documentary, it reminded me of my interview with Jesse. A lot of what Jesse says about the power of art in raising social consciousness reminds me of Marley’s purity and mission of uniting people through his lyrics. In living proof of their connection, last we spoke, Jesse had seen the documentary 3 times.

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