The Art Of Whimsy with Jenna O’Brien

There are rare moments in life when you encounter someone whose joy feels woven so deeply into the very fabric of their being, that it seems to illuminate the room when they enter. Our Du Muse, Jenna O’Brien, is one of those people. Her warmth is immediate as she walks into the cafe to greet us, a bright smile glowing on her face.

With her whimsical way of seeing the world, it’s no surprise Jenna is a multifaceted artist. As an illustrator and the writer behind Feeling! Magazine on Substack, Jenna is the kind of muse that makes us want to live life a little fuller, take the scenic way home, and add a pop of color into an outfit, just because.

We meet up in Brooklyn Heights, one of Jenna’s favorite areas in the city. She details the small businesses she loves visiting here and how she adores the juxtaposition of these treelined neighborhoods with the massive Manhattan skyline in the distance. We plan to meet at Náko for matcha and pastries, walk through the historic cobblestone streets, and finish at the waterfront and explore until our feet grow tired.

Jenna's Hot Takes:

Cashmere or Silk?

Cashmere

Heels or Flats?

Flats

Digital Illustration or Hand Illustration?

Digital

Warm Tones or Cool Tones?

Cool Tones

Matcha or Coffee?

Matcha

What Du & Berry piece is the most “Jenna”?

I think honestly these cashmere polos [gestures to our Cashmere Polo Top she’s wearing]. I have the pink one already. I just love that you can customize the bow, I love a color switch option. I can pick a pop of pink or grey and it just feels very me, very classic and cashmere.

How would you describe your personal style in a few words, and how has it evolved over time?

I think I always have a bend towards color but I really am drawn to more of a classic silhouette. I think over time I’ve become more interested in a wardrobe that is more timeless. I used to try to hit a trend at the right time but now I just really gravitate towards clothes that I feel I can have forever.

When looking for new wardrobe pieces, what are some features you search for?

I’m always trying to strike classic with an element of something fresh, something whimsical. So, it’s like a classic silhouette but it’s in a color it wouldn’t normally come in or it’s something like this [points to her Cashmere Polo Top]. It’s a classic polo but it has this fun little element of a bow. I feel like I’m always trying to marry the extra whimsical thing with a classic look.

Speaking of whimsy, we take our matcha to go and head outside to literally stop and smell the flowers. I ask Jenna how she defines whimsy, since it plays such an integral role in her art.

“Whimsy is definitely a trending word,” she says, “but I would describe it as more of a tangible practice of joy, like participating in practices that truly fill you with hope.”

I ask her why she finds it so essential. Jenna’s answer is simple: Whimsy and joy are essential because life is really hard.

“I think our thoughts and what we dwell on become the world we live in. So, to me,” Jenna explains, “it’s really an essential part of being human; this practice of even if things are terrible I’m going to put flowers on the table.”

She then tells me something that has stuck with me ever since.

“Hope is like a muscle to strengthen,” she says, “It’s not just a natural thing you’re going to happen upon. I think this practice of reading things that make you smile or making things with your hands or inviting people into your life that you really love and enjoy is absolutely an essential part of being a human.”

“And,” she continues, “that’s how I want my work to feel to people; something in their home that reminds them that everything is going to be okay. Whimsy isn’t an aesthetic or something you buy. It’s more of like a daily practice, like what do you do with your hands, what do you do with your heart, how do you serve others, how do you bring other people into your life and make their lives better? And I always say, if you want more joy the first thing to do is give more joy away and you’ll quickly find it.”

What advice would you offer to emerging artists who are still in the process of finding their voice?

You have to actually do something that you love to do. Like the action itself has to bring you joy and that is the only thing that will sustain long creative work, not the results, not how it performs but do you have fun when you do it?

Would you describe your creative process as more intuitive or conceptual, and how does that shape your work?

I think it’s a bit of both. I have my own ideas that come naturally and then usually, I feel like a lot of my work is very narrative focused, bc I love writing and I love design and I love marrying those all the design is tying to tell the same story that my words are trying to tell, so I feel like a concept really a story is what draws my color palettes together, whether I ever write the story or not its all story based.

We stop for a quick outfit change before trekking to the pier. I tell her I’m obsessed with the pop of blue in her shoe styling, the pop of yellow in her sunglasses.

Are there any unexpected sources of inspiration that influence the way you dress?

My grandparents! I think of both my Granna and my Grandpa often. My Granna has a timeless style. I’m from Florida, so there’s a southern charm there with pearls and classic silhouettes. She’s always worn the same clothes and so I want to buy pieces that last me forever. I feel like my Grandpa honestly influences me too. He’s worn boat shoes, a crisp white t-shirt and a braided belt my whole life and I think of them all the time when I go shopping. It’s really funny.

You work a lot with intersection of design and feeling, what’s your favorite way of communicating a feeling through design?

My favorite way to marry design and feeling is through color. I make color palettes a lot and I’m very specific about the exact hue I choose and the name. And usually when I put a palette together, I have written a story that no-one knows and I piece them together to tell that story completely in a way that feels like it means something to anyone looking at it. For me, color is the ultimate way and universally we feel things by color.

Our interview comes to a close with the Manhattan skyline in the distance and the breeze of the waterside cooling us from the trail. For a few moments, we stop and just watch the waves undulate below us.

We thank Jenna for taking us here, and for reminding us to stay whimsical. After we part ways, I make my usual trip to drop off a few rolls of film for development. I find myself pausing on each street corner to simply look. Though I’ve walked that path a hundred times, I noticed something new on each block; a detail, a doorway, a glimpse of whimsy, perhaps. There is so much beauty to see, so many experiences to have, so much joy to feel, but only if you stop to seek it.