DRESS TO IMPRESS, 152: A Conversation with Anna Murphy, Artist selected for Woodford Reserve’s Derby Bottle

By Mckenna Graham • Photos By Matt Johnson, Henry ‘Eli’ Branson & Tuan Tran 

The image on the Woodford Reserve Derby bottle may be small but artist Anna Murphy has managed to distill the energy of her typically massive murals into this year’s design. Known for her distinctive blue and white porcelain-inspired painting style, Murphy credits the Derby for her very existence since her English father met her Kentuckian mother during a business trip to Frankfort to insure a racehorse. The artwork she created to commemorate this year’s bottle titled, Dress to Impress, 152, utilizes a bold color palette of cerulean blue and crimson layered over a background of gold-- the first ever Woodford Derby bottle to feature gold foil. From the hats, fascinators and scarves to the seersucker suits, bowties and bowlers, Murphy’s painting celebrates the best of Derby vestments and the jubilant spirit that goes with it. Murphy says, creating the artwork for the Derby label has inspired her to start her own fashion line that will be launching soon. If you are interested in learning more about this and keeping up with Murphy’s ongoing creative endeavors, you can follow her @annapmurphy on Instagram. 

She kindly shared her time with us to talk more about her creative process and becoming a part of bourbon and Derby history. 

What was your creative process in creating Dress to Impress, 152? How did you decide what subject matter would make its way into the frame? 

When I began thinking about the artwork, I kept returning to one of the most distinctive aspects of Derby day. The extraordinary fashion. The hats, the color, the bold self-expression, while also wanting to depict the shared feeling of celebration, anticipation, and tradition. I wanted the artwork to capture that energy and elegance while still honoring the heart of the Derby: the horse and the race itself. The composition became a balance between movement and celebration, placing the horse and jockey at the center while surrounding them with symbolic elements that evoke the spirit of the event. 

Florals played an important role in the piece. The Derby roses are iconic, of course, but I also incorporated additional flowers that carry symbolic meaning. Representing themes like devotion, transformation, and protection during travel. Together they create a visual language that reflects both the beauty and the emotional resonance of Derby day. With a gold background, evoking the feeling of celebration and luxury. 

It took at least a dozen different design renditions before we landed on this one. With many different scenes and perspectives of the race. I could not be happier with how the final label turned out. I felt I was able to honor the magic of the Derby, while also keeping my authentic artistic language and style. 

It will always be a very special project and memory for me, as I painted the original artwork (on canvas) two weeks before I gave birth to my son, and was able to put the final touches on it a week after we brought him home from the hospital. So it was created during a very special time! I also love the coincidence that my view outside of our hospital room window was the Chicago Museum of Contemporary art. 

Did you have any source imagery for the jockey or horse? Anyone we might know? 

Rather than referencing a specific jockey or horse, I approached the figures as archetypes of the sport. I studied the posture and movement of thoroughbred racehorses and jockeys to capture the sense of speed, tension, and elegance that defines the moment during a race. 

The goal was not to portray a particular individual but to represent the timeless spirit of the sport, and the athletic partnership between horse and rider that makes the Derby such a powerful spectacle. 

What is your medium of choice and what medium did you use to create this image? 

My background is rooted in traditional painting in oil. However, for the last decade acrylic has been one of my preferred mediums because of its versatility and ability to build vibrant layers of color and texture. For this artwork, I began by sketching the composition directly onto canvas and developed the final piece using acrylic paint. 

The original painting measured roughly 30 inches in length, which presented an interesting challenge since the final artwork would ultimately be reproduced at a much smaller scale on the bottle label. Because of that, I had to be very intentional about the level of detail in the painting. Certain elements needed to remain bold and legible when reduced in size, while still preserving the richness and intricacy that make a painting feel alive. 

It became a careful balance between detail and clarity. Thinking about how the composition, color contrasts, and key focal points would translate from a large canvas to a small format. 

Have you done other equestrian art in the past? 

This was my first time creating a work centered around a racehorse, which made the process especially exciting. While horses have not been a primary subject in my past work, the theme fits very naturally within my broader artistic interests. 

Much of my work focuses on nature, botanical elements, and the relationship between humans and the natural world. Horses embody many of those same qualities; strength, elegance, movement, and a kind of quiet harmony and power. In this painting I was able to explore that energy while also incorporating the human figure and the expressive fashion that is such an iconic part of the Derby tradition. 

What is your favorite way to drink bourbon? 

I usually prefer it straight or on the rocks. That way you can really appreciate the craftsmanship and depth of flavor. It’s a drink that rewards slowing down and taking the time to savor it. 

Do you have any favorite Derby memories that may have inspired you? 

One of the reasons the Derby has always felt meaningful to me is because it’s actually part of my own family’s origin story. 

What makes this moment even more special is that this year will be my first time actually attending the Derby in person. I’ll also be bringing my son, who isn’t even a year old yet. There’s something really beautiful about sharing this tradition with the next generation of my family.