Fashion jewelry retailing is in Ashleigh Bergman’s blood. You could say she was born to be styled.

There’s no one way to become an expert in fashion jewelry retailing. But Ashleigh Bergman’s career so far amounts to a doctorate on the topic. When she was 14, Bergman, who is now 40, began selling jewelry at the iconic Los Angeles boutique Fred ­Segal. She remained there for 18 years, becoming a trusted jewelry consultant and buyer for the retailer. During her tenure, she even developed a jewelry collection with Nina Segal, Fred’s daughter.

Bergman was eventually tapped by Anthropologie, where she was tasked with bringing more branded jewelry into the global retailer’s merchandise mix. The learning curve was steep, she recalls—so much so, she likens her time at Anthropologie to “free grad school.” Ultimately, however, “it was much more about spreadsheets and numbers,” she says. And she missed working directly with jewelry consumers.

In 2015, Bergman founded the virtual jewelry boutique Milestones by Ashleigh Bergman, which merges online and social retailing with an in-person component—clients can visit the brand’s new light-filled showroom in L.A.’s Laurel Canyon. The business satisfies Bergman’s love of working one-on-one, with both clients and jewelry makers. “At the end of the day, I like talking to people,” she says. “I’m a retail girl. No one loves the smell of Windex on glass more than I do!”

You have so much experience in physical retailing. What made you decide to be a digital retailer?

I love brick-and-mortar retailing, but I know that’s not where things are right now. So I try to create a ­comfortable feeling in my online space. When I left Anthropologie, I was always personal-shopping for people. I would call brands, and they would give me merchandise on memo. I started posting styles on Instagram, and people were buying things from me from all over the world. I love the access I have to so many more people online.

You’re the primary model on your company’s Instagram and are face-forward on the website, too. What played into your decision to be so visible in the business?

In the beginning, it was only about the jewelry. I didn’t put my face on it. Then I started realizing—looking back to my Fred Segal days with me on the sales floor—that putting my face on the brand helps to establish trust with people. I started showing myself and started having personal ­relationships with my clients. We would be talking about our kids, and just the craziest things. The brand is me. Ninety-nine percent of the jewelry on the site is photographed by me. Every time I’m in a showroom, people are like, “Can I help you take a photo?” And I’m like, “No, I’ve done this for thousands of years, and have taken thousands of pictures of myself.”

I would imagine being the face of your company also sets you apart from your competitors.

I try hard not to look too much at what others are doing and compare. But I have to say that the one thing that sets me apart is me. I’m not reinventing the wheel. But no one is me. No one puts it together like me, no one looks like me and talks like me and has my sense of humor. It’s a vibe. I’m not better than anyone else and no one else is better than me. If you like more of a laid-back L.A. vibe with a twist of lemon, then you like me.

You’ve collaborated with some well-known designers including Ariel Gordon, Maya Brenner, and Walters Faith for your Ashleigh Bergman Collective jewelry series. How did that collection come to be?

The collective came about in 2019 after I’d worked closely with a few brands for over a decade. It was a one-time thing, but we still sell the pieces. I didn’t want to create a collection, but I’m a designer and I do have ideas of things I want to create that aren’t in the market. It started with me ­working on one piece with one designer, then it was like, “What if I pick my favorite designers and I make one or two pieces and create a little collection?” They sell it and I sell it.

What made you want to open a by-appointment space?

I created a space that’s really inspiring and calming in Laurel Canyon. It’s invite-only, but also my door is always open. When I meet people online who are local, they can come in now and see things in real life, which is nice. I think it’s about being flexible. I’ve brought people jewelry everywhere. I can’t tell you how many shady grocery store parking lot handoffs I’ve done!

(Portraits: Kim Butan/Cloth + Stone Photography)