I asked her about the business she was opening in Old Town. Her confidence and calm was something that instantly put me at ease. As she shared her journey, she felt like one of my girlfriends – and we had just met. This was going to be her third location, she was already a seasoned entrepreneur. Even a slight delay here or there wasn’t going to stop her momentum.

“I’m not an extrovert, I had to develop it, I was the bookworm, the youngest in a big, boisterous family,” says Stephanie Woodland Kelly. “I have five brothers and a sister. When I got to college I had to learn how to develop those skills. I’m glad there were no mobile phones back then. The mistakes I made…it wasn’t a big deal.” 

I first met Ana at an evening event at American in Paris. Her long, shiny black hair caught my eye and I enviously asked if it was naturally straight or if she had to blow dry, flatiron and put a ton of product in it like me. She smiled and said “blow dryer,” but I knew that she was just born lucky with great hair. When Renée and I arrived for her Street Style shoot, we knew she needed little direction, she carries herself with incredible style and grace.

When I ask Tristan what he’s really enjoyed learning about the jewelry business he says it's the mystery of estate jewelry. He says it’s one of the most popular and browsed upon cases – because everything inside is so unique. He also loves the possibilities that come with redesigning pieces and family heirlooms, so that future generations can wear a piece of their family history.

I kept seeing Suzanne Thibeault’s face on social. She was in group shots on LinkedIn, at openings on Insta…in recaps of networking events. Who was this woman? Then I saw her in person. I felt like one of the cool kids when I was invited to a VIP party for the opening of Atlas Brew Works and Andy’s Pizza in Carlyle, and there she was. I introduced myself by sharing that she was my professional girl crush, because she was making moves. She was not freaked out.

Shara has always had an entrepreneurial mindset. “You get out of school and think they’ll teach me how to run a business. But that doesn’t happen in the chiropractic industry…they make you their workhorse, and you just adjust clients, and don’t learn how to run things. There are people who can’t work for others and figure things out for themselves. That was me.” 

The first thing I notice as I walk into Old Town Books Junior is the tree. It is magical. Its leaves. Its trunk. The pillows strewn in front. “It’s the first thing I wanted,” says Ally Kirkpatrick. “I researched the tree before the store designer. I wanted a moment, a beautiful memorable thing. If I were a little kid, I’d remember the tree."

Many know Vanessa for her illustrations; she launched Old Town Illustrated during the pandemic. “When I moved here in 2021, I was just walking around Old Town and my mom’s husband pointed at the black plaques on homes. He said it meant they held at least 100 years of history. I’m very visual, so I immediately began picturing them (the homes) as illustrations.”

Janel is one of those women who just has a presence. Yes, she’s naturally beautiful, and I’ve seen her with hair up in a bun, clad in sweats and she still looks flawless (she’s my neighbor). It’s the energy she gives off, her openness; her eyes carry no judgment. She’s seen a lot, she’s experienced a lot, and it has given her tremendous empathy.

I must share that I've never seen Hattie – without Tiffani. They seem somewhat attached at the hip, not like Siamese twins, but in an endearing, “I got your back and if anyone messes with you, they’re messing with me” kind of way. They met at the University of Georgia in 2008, and became best friends and roommates. “And we’ve been roommates ever since,” says Hattie. 

Holly steps out of Maria’s car and is rocking a kick-ass ensemble. Minutes later, she is literally stopping traffic. Renée has posed her across the double yellow lines on Royal Street, a few hundred feet from King Street. None of the cars I’m halting seem to mind; they’re taking in the scene of four women scrambling around the pavement in 90 degree heat.

Emily always circles back to wanting to make people feel safe. Safe talking about taboo topics, safe finding products they need, and safe in sharing uncomfortable symptoms they may be too embarrassed to share with their partner or friends. That’s what’s so amazing about her – a woman passionate about making taboo topics not taboo. 

“We’re surrounded by history, American history – not political history. In England, the local pub is part of your community, you walk in and you know people. I want that here. I love the walkability of Old Town, the character in the architecture. Sometimes I close my eyes and can almost hear the hooves clanking from horse-drawn carriages.”

Natalie says, “You can keep an eye on your clients and work out. There’s an energy transfer when we’re doing it together…we know when we’ve fatigued…that’s harder to tell when you’re not actually doing it. I also give my team the freedom to bring their own flair to their class, it’s not plug and play.”

“Coming from Old Town Alexandria, I wanted to open my first restaurant here. Restaurant Eve was born, named for my daughter. I didn’t want it to fail so I named it after her. We were very fortunate, we received four out of four stars from The Washington Post…served two sitting presidents. After Eve, I opened 14 restaurants…”

“I was having dinner at Landini’s and I walked right past Courtney and her husband. And she stopped me and said, ‘Oh my God, what have you been doing?’ I shared that I was getting my masters in interior design and she said, ‘You’re going to work for me when you graduate.’ Once I moved back here, I reached out to her immediately.” 

Ashley’s background has been in surgical medicine for the past 20 years. “I’m an artist, and even though I can’t draw, I can paint your face. I can see the angles of your face, that's what injectable medicine is. It’s not replacing plastic surgery, it’s supporting your face. It’s changing the way your face catches the light.”

“It was my senior year of college when we reconnected. We were all in Old Town the night before Thanksgiving; I was with my Ireton girls and he was with the boys. We hadn’t seen each other since high school. After that, we kept in touch…AOL chat,” she says laughing.

Don prefers to paint live, and not from a photograph. When someone is sitting for him, “the real personality traits come out, and you have to put that in the painting.” A portrait can take up to six months to complete; he’s not churning them out. “The sittings are part of the experience.”

“Storytelling is so important to me, digging in and explaining the art and science behind architecture. All of my experiences in operations and comms led me here, and I’m so grateful for my career and to work for a local small business, where I’m raising my family.”