At first meet, Natalie O’Connor is a whirlwind of energy, gliding across the wood floor of her art loft, from painting to painting, explaining the artist’s journey, shuffling back to open a window, offer a chair, show us more paintings, offer us champagne. Yes, please, it’s 5 o’clock somewhere. 

She has that entrepreneurial energy that consists of making every minute count because – every minute does count when you’re launching a new business. Natalie is Florida-born and raised. She’s a mix of Cuban, British, Irish and speaks fluent Spanish and some Arabic. At one point she had wanted to be an attorney and practice international law. She studied political science and psychology, but her true passion was always art.

Natalie worked for major law firms and in legal matters for the World Bank. “I loved it, but my passion for art always came back. I taught myself how to use my skill set to create legal documents for international artists. I’ve always wanted to support and defend those that could not defend themselves…this includes artists in lesser developed nations. They need a voice. Being strong for others is the commonality. Helping them use creative avenues to solve problems ties it all together,” she shares.

Her Cuban background formed a natural alignment with her specialization in Cuban art. “I go to all the art fairs annually, and I visit Cuba quite often. The artists I represent have become like family.” It was through her work at the World Bank and other events, that she began this artful connection. She has been traveling to Cuba for the past 15 years, meeting, “incredible people.”

She has become quite familiarized with transporting art internationally and preparing the proper paperwork and assisting artists in the process. “I have shipped crates of art from Cuba to Europe and then here…it’s much easier to transport art from those that are still living, than from those who are deceased.” 

Originally from Naples, Florida, a small quaint town, she has loved Old Town since her post-graduate days. “I didn’t want to just stay in Florida, I wanted to be exposed to different cultures. I always thought Old Town was beautiful, the cobblestone streets, the waterfront…it’s quiet, it’s safe.”

Her space is not just an art gallery that sells work, but also a cultural space with occasional workshops, dinners and immersive experiences. “I bring in contemporary, respected pieces and conceptual art works that educate and move people. I have artworks that aren’t found in typical galleries. Most of the artists I work with are in major international museums.” She makes it multidimensional by bringing in music, film, cuisine and live performances that help people better connect with the artwork. “There will be someone singing…someone playing the guitar. For a Lebanese art display, we had an oud…I’ve had a Cuban three-piece band. I’ve had a pianist, a conga player and a saxophone player. I have a lot of friends who play guitar, and they’re extremely talented.” 

When she visits her artists in Cuba, she brings the missing pieces. “It’s hard to see these geniuses make the most beautiful things while they’re missing components. I bring materials in multiple suitcases, including heavy acrylic paints, art supplies, whatever canvas I can cut up and fit in my suitcase…and food. Trips to Cuba are always an adventure, and although I see so many people struggling, there is also a beauty to it. They have learned how to enjoy each other and life, despite the challenges. Sometimes here, we lose ourselves in the daily grind.” 

I ask if I can join her sometime, and she nods, “I do offer curated trips to Cuba with personalized itineraries. I have found the best tobacco farms, and I facilitate everything, and bring along a translator…and I have my own drivers.” 

She’s excited for her property that she’s renovating in Old Havana. “It’s a block away from the restaurants where you can hear live bands. Like Old Town, they have cobblestone streets, it’s close to the museums, and everything is quiet by 10pm. When I’m there, I feel grounded. You have to limit your internet and phone access, the signal isn’t strong. You can buy internet cards, but they run out quickly, so you only use them occasionally…every web search is intentional, you don’t just surf the internet.” 

Natalie loves representing artists because each piece is so meaningful. “I don’t want to just sell the piece, I want to pair a client with the perfect artwork…matching a piece with someone’s personality. Art changes your home; it affects your mood. I do home visits, too, to help the buyer with where and how to place it. I get that from my mom, she’s an interior designer.” 

In her spare time, Natalie says she’s more about enjoying unique life experiences than shopping. “I like to look nice and I like pretty things, but I rather explore interesting destinations within driving distance. I always want to see something else…something I haven’t seen before.” 

See Natalie’s client portfolio and check out her Street Style:

ABOUT NATALIE

Neighborhood: Old Town, Alexandria

What is your hometown? Naples, Florida

What would surprise people about you?  I am a property owner and patron of the arts in Old Havana, Cuba; providing resources and support to local artists.

Favorite movie: I appreciate many different genres; ranging from Pulp Fiction to biological films on artists (Frida Kahlo, Pollock, etc.).

Guilty Pleasure: Playing international music and creating art.

Latest binge-watch: Mozart in the Jungle.

Bucket list travel destination: I’d like to travel the world, but out of countries I haven’t visited, Thailand is a top choice.

STYLE

Define your style in three words or less: Elegant, artsy, understated.

The go-to piece in your wardrobe: Black dress.

Favorite trend: I don’t really follow trends, I like whatever catches my eye.

Beauty product you can’t live without: A good foundation and long-lash mascara are my favorite combination.

Boots, sandals or sneakers? Heels.

WELLNESS

Go-to way to de-stress: Listening to music or visiting a winery.

Most fun way to stay active: Dancing or exploring new cities.

Wellness goal: Getting back into yoga.

Want to try: Mindful meditation practices.

Proudest wellness achievement: Genuinely loving healthy food.

HOME

Favorite room in your home: My entertainment room with my fireplace and record player.

Antiques, modern, or a mix? Mix.

Last item bought for your home: Spanish tiles for my Havana property.

Favorite way to entertain: With a bottle of bold red wine, charcuterie and great music.

Clutter-free or well-lived in? Clutter-free, though the artist in me isn’t perfect. ;)

Next planned purchase: Potentially a property in Virginia or Florida.

ALEXANDRIA

What do you love about Alexandria Stylebook? I like the concentration and highlight they give to female entrepreneurs in the area. The high energy of the staff and their charisma really makes the connection easy. 

Favorite spot in Alexandria: As a Floridian, I enjoy being by the water, but often visit the bands at 219.

Your go-to shop: Old Town Farmers’ Market.

Best food spot: Rex or Ada’s on The River.

Favorite annual Alexandria event: Old Town Festival of Speed & Style.

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