Q&A | JaKenna Gilbert

Photos of Jakenna by Thomas Gilbert.

Have you ever had one of those moments where you say to yourself: this person is eerily like me? I did when I met JaKenna Gilbert. Her style is something I am hugely on board with (you may have already noticed my affinity for those red J. Brand jeans), and I fully endorse her Q&A as well.

If not in New York, I would live in...South Africa. When I was an undergraduate at Duke, I traveled there for a paleoanthropology field school program and fell in love! I used to wake up every morning, step outside of my tent and brush my teeth as the sun rose over the mountains. That’s a memory that sticks with you.

My dream holiday would be to...first, adventuring around Costa Rica to ride horses, jump off of waterfalls and surf at sunset. Next, off to Argentina for Yerba Mate, a late dinner, all night dancing and eventually wandering into a breakfast spot for early morning sustenance.

My current obsessions are...eating Fage Greek Yogurt; listening to Etta James on repeat as I get ready in the morning; wearing bold-colored denim, men’s chambray shirts, five-inch back velvet wedge platforms and platinum Sperry Top Siders; shopping at TopShop, Uniqlo, and when I can afford it, Alice + Olivia and Michael Kors.

I channel my childhood self when I...read before bed. When I was eight, I read one chapter of The Secret Garden every night and the ritual stuck with me. It’s the first book I ever read alone and entirely to myself.

The fictional character I most relate to is...Lula Mae. She came from humble, country beginnings and transformed herself into the glamorously citified, yet somehow down-to-earth Holly Golightly. The high-class call girl thing isn’t really my style, but the girl knows what she wants and how to get it. Respect.

If I had to be outdoors all day I would...Walk the entirety of New York City, exploring the neighborhoods and experiencing how one culture blends into the next. Tasting the foods, smelling the aromas and definitely people-watching to the maximum. I’d start in the Financial District, head to Chinatown, then the Lower East Side/East Village, up through Gramercy, cut over to Chelsea and the Theater District, walk along Central Park and the Upper West Side and end in Harlem. Perfect, isn’t it?

My favorite quality in a man is...patience and forgiveness. I make a lot of mistakes and require a lot of patience.

My favorite quality in a woman is...support. Women need to support each other, raise each other up, be excited when one of us succeeds and saddened when one of us fails.

I’m terrified of...never realizing my full potential.

My dream car is a...1969 Mercedes Benz 280 SE 3.5 Coupe. Classic. But don’t tell my boss!

My cocktail of choice is...Glenfiddich. Neat.

My celebrity crush is...Lake Bell. And Ryan Gosling. Have you seen the YouTube video of him breaking up the fight in NYC? Hot.

My friends and I like to...drink, eat, dance, and shop. Not necessarily in that order and boys are rarely allowed.

My beauty product of choice is...mascara! Give me jet-black and pump up the volume please.

If I could go back in time for one decade it would be...the 1960s. The topic of race specifically intrigues me as I’m of mixed race. My father is black, my mother Irish and I’ve grown up with a very open view regarding race. I would have fought for a couple like them to be together; otherwise, I wouldn’t be here!

As a teenager I was totally into...sports and school. And boys, boys, boys.

I tend to splurge on...clothes. Surprise!

Wearing men’s shirts, drinking single malt whiskey and using my feminine intuition and intellect to succeed in this world...is what makes me have Tomboy Style.