Jenny Jackson is the New York Times bestselling author of Pineapple Street, a Good Morning America Book Club pick that has been published around the world in more than a dozen languages. A graduate of Williams College and the Columbia Publishing Course, Jenny is currently Vice President and Editorial Director of Fiction at Alfred A. Knopf, a division of Penguin Random House. She lives in Brooklyn Heights with her family.

First things first – tell us a bit about yourself!

I’m a lifelong reader and lover of books. I basically schemed my whole life to try and find a way to get paid to read books. When I was in college, I had a summer job as a receptionist, and I kept getting in trouble for reading at my desk! So, when I was 22, I got hired as an editorial assistant at a publishing house and never left. I’m now the Editorial Director of Fiction and I edit and publish a range of commercial and literary fiction, from Gabrielle Zevin’s Tomorrow, and Tomorrow, and Tomorrow to Kevin Kwan’s Crazy Rich Asians, from Helen Fielding’s Bridget Jones: Mad About the Boy to Emily St. John Mandel’s Station Eleven. Then, during lockdown, I went sort of crazy and wrote a novel, Pineapple Street, which was published by Pamela Dorman Books.

Jenny wears the Fiona Convertible™ Mini Dress in yellow/ivory

Your debut novel Pineapple Street was an addictive deep dive into the lives of the uber rich. What inspired you to write about this specific family?

My neighborhood, Brooklyn Heights, is such a funny place. It’s just across the river from Manhattan, known as “America’s first suburb,” and it’s simultaneously incredibly quiet and home to such hidden wealth. At my kids’ preschool auction, they gave away a child-sized Tesla and Botox parties. They auctioned off a school teddy bear for ten thousand dollars. It was insane. During the pandemic I wasn’t going anywhere so I would just wander around the neighborhood and look at people’s windows and daydream about what was going on inside.

Similarly to Darley (the character in the book), Mestiza New York was founded by two women who are also balancing motherhood with their careers. While it is challenging at times, it is also rewarding. With this being said, what is a word of advice you have for other women who are looking to balance both sides of their lives?

I think it’s both fitting and hilarious that Mestiza founder Louisa and I first met at a “Reptile Experience” in Florida surrounded by two dozen screaming children petting giant snakes. We were each on vacation with our families, totally unplugged, dressed in flip flops, just enjoying our kids. (Neither of us was particularly enjoying the snakes, to be honest.) I spent the first couple years of parenthood trying to hide the fact that I had kids from my boss—sneaking to the second floor to pump, feeling guilty if I had to run out to take my child to the doctor. I realize now that I was wasting so much energy worrying about people judging me, thinking I was less committed to work because of my children. The reality is that being a parent has made me better at my job in so many ways. Sure, I sometimes leave early to go to a recital, but I am more efficient at my desk, and I handle so many of the emotional aspects of my job better now. I wasted years feeling guilty and apologizing for something I shouldn’t have.  

After being an editor for two decades, what inspired you to get back into writing? What do you love about being an editor? 

I really wrote Pineapple Street because I was lonely. It was 2020 and I missed parties and friends and gossip. So, I wrote a novel where all the characters get to go out all the time and do all the things I longed for! Even though I love writing, I could never leave my job as an editor. It’s exhilarating to discover a new talent, to help a writer shape a story, to come up with ideas for structure, to work with the art department to design a jacket. For me, there is nothing more exciting than getting a manuscript on submission from a literary agent, staying up all night reading the pages, and then bursting into the office the next morning to tell all my colleagues about it.

 In your words, what is the core theme of Pineapple Street? What story were you aiming to tell when you first started writing it? And how has that evolved (if at all!)

I was inspired by an article I read in the New York Times called “The Rich Kids Who Want to Tear Down Capitalism” by Zoe Beery. It was about these socially-minded millennial heirs who find their fortunes at odds with their values. This really got me thinking about what it might mean to be a rich kid in America right now, in this age of income inequality and anti-capitalist sentiment. Is it possible to be rich and good at the same time? Is generational wealth inherently corrupt? But of course, I am fundamentally incapable of seeing anything as truly black and white, so I came to really love my characters and have incredible sympathy for them. So, where shows like “Succession” and “White Lotus” really focus on terrible rich people, Pineapple Street focuses on characters trying to do the right thing while often getting it all wrong.

Do you see yourself in any of the characters that you write? If yes, how does that make you feel?

I see myself in all of my characters. I end up weaving in tons of autobiographical detail, but then messing it all up to the point where it’s unrecognizable. Georgianna, for example, works for a nonprofit and falls in love with an older colleague. They end up having a love affair. When I was young, I worked at the same kind of nonprofit and had a huge crush on an older colleague. But I don’t think he knew I had a crush on him and there was certainly no love affair. (This is why writing fiction is total wish-fulfillment!) I think that as a writer you have to put a lot of yourself into your characters—even the ones you hate.

Which Mestiza dress are you wearing to one of Tilda Stockton’s fabulous parties at Pineapple Street? And why is this the perfect fit? 

The Valencia is absolutely the dress for a Tilda Stockton party. Sometimes it’s tricky to figure out what to wear to a weeknight cocktail party. You know some guests will be coming directly from work, but you also want to look festive and pretty. The buttons and belt on the Valencia make it feel like the perfect bridge between two worlds.

Can you give us a little sneak peek at what your next book is about?

My next book, coming out in June of 2026, is the story of a group of friends in their thirties, some settled down and married with kids, some still single and wild, and the way an accidental pregnancy both brings the group together and tears them apart. It’s set in the town where I grew up, on the beach north of Boston, and it gives me the chance to write a lot about how funny and weird it is to raise small children alongside your friends.  

What do you love about the Mestiza brand?

Mestiza has such great colors. Living in New York it’s easy to wear black all the time. There are days where I look around our editorial meeting and realize we’re all in various shades of black and gray.

How does wearing your Mestiza piece make you feel?

I feel ready to go to a party—and, since I basically wrote Pineapple Street because I wanted to be invited to a party, you know that makes me happy.