Roots and wings.

Where I came from and where I am going.

Rooted in the south, destination unknown.

I was born the youngest of 4 siblings and the only girl. Naturally, I had a very special bond with my mother.

Kentucky Gypsy | Mom and Lisa | Roots
Mom and I, circa 1990

Among several beautiful connections, we both especially enjoyed jewelry. For as far back as I can remember, I would walk into her bedroom, over to her armoire, and pull out drawers of all of her coveted pieces. Charm bracelets, gaudy costume jewels, diamonds, and pearls. Her collection was unlike any other. While she would get ready, I would play dress-up. There was a story behind each and every piece. It shouldn’t be surprising that by the time I was in high school my collection started to resemble her’s.

I remember making beaded bracelets as early as age 6 – several can be found in my mother’s jewelry box today.

My journey as an entrepreneur began in 2011. Stephen Tyler was on the cover of Rolling Stone magazine with feathers in his hair and I thought to myself, “Where have I seen this before?!”. I was reminded that I had a box of these very feathers in our basement…. When I was younger, fishing was usual with my dad and brothers and fly fishing was my favorite, not because of the event itself but because of the unique lures that I was fascinated with. That summer, I figured out how to translate the art of fly tying into the art of feather earrings. (I still have the first pair I made and WOW, they have evolved since then.)

Kentucky Gypsy | Feather Earrings 2011 | Handmade Jewelry
Handmade feather earrings, 2011

In the summer of 2011, I wore my first handmade earrings every day while I worked as a server at P.F. Chang’s. Before long, every female in the building had bought a pair from me and also wore them to work. Soon after that, I started filling my apron with zip lock bags of earrings and when guests would ask about the jewelry, I would lay them out on the table and come back making several sales. My makeshift summer business turned a profit, and it was well timed.

As I transferred from the University of Alabama to the University of Kentucky, I explored several majors. From Interior Design to Art Studio, I concocted my own educational cocktail that was both new and potent. I enjoyed studying painting, installation, fiber arts, and costume design and opted out of all things business. Oops.

Kentucky Gypsy | Textile Design | Roots
Hand felting a wool wall hanging “Candyland,” school project – April 2011

This led me to apply to an exchange program at Cal State LA that would change my life forever. I moved to Los Angeles on August 4th, 2011. Nine months of classes in fashion design set the tone for a future in the industry. In my first months in LA, I used the money I made selling earrings to get settled. The funny thing is that once I was at school, I did not make or sell a single piece of jewelry.

Kentucky Gypsy | Fashion Design | Roots
Handmade corset and beaded collar, Avant Garde school project, 2012

When I graduated in May of 2012, I volunteered and found freelance jobs doing window display installations, dressing models at fashion shows, styling photo shoots, assisting in planning events, maintaining e-commerce sites, and managing social media.

Kentucky Gypsy | Window Display Installation | Roots
Beverly Hills, Collaboration of the “Kusama Tsunami” Window Installation, 2012  
Kentucky Gypsy | Styling and Art Direction | Roots
Styling and Art Direction,  Mark Sacro Studio – Long Beach, 2015 Photo Credit: Jaime Anderson,
Kentucky Gypsy | Fashion Show Volunteer | Roots
Fashion Show Volunteer, Hollywood, September 2011

I cannot count the number of startup companies that I took part in. There was never a dull moment, since not having a “real job” forced me to hustle and do whatever it took to pay my rent and to live the lifestyle that I was constantly curating. During this time, I didn’t worry about a career plan. Some would feel anxiety with this lack of a “roadmap”, but I was perfectly content making it up as I went.

Kentucky Gypsy | Sunset Blvd | Roots
Sunset Blvd, 2013

A regular customer at one of my many odd jobs put it best. One day he came in, right on schedule, and I asked how he was doing… He replied, “Lisa, I am a human being, not a human doing… let me be!”  FEELS.

My carefree and wanderlust mentality took a sudden shift when I found myself back home in Kentucky taking care of my recently diagnosed mother.


Kentucky Gypsy | Brester Family | Roots
The Brester Family, March 2016


Caretaking was wonderful, and I cherish every moment that I had with my Mom. It was also incredibly stressful and exhausting. Honestly, it was a complete mind fuck. Despite my best efforts to keep my sparkle at all times, my mom knew I needed a creative outlet. She suggested that I should pull out all of my old jewelry making supplies. From that day on, when mom was resting, I made jewelry. And when she was awake, I would show her what I’d made. When she would rest more, I put my head in the “how to’s” on starting a business. We talked a lot about different names, but more so about my lifestyle. I had moved around even before LA and when I told people “My name is Lisa, and I’m from Kentucky” I’d get… KENTUCKY!? My mom was supportive, encouraging and unceasingly thoughtful until the very end.

Thanks to my ultimate cheerleader, Kentucky Gypsy was born.

Kentucky Gypsy | Lisa Brester | Roots