Model Behavior 2025: Deby Pitts

As an avid gardener and community leader, Deby Pitts felt an immediate connection with Cheekwood Estate & Gardens when she first visited with her husband, Keith Pitts, and their children. After moving to Nashville in August 1992, Deby and her young family often stopped by the estate to take in its natural beauty and magnificent art. 

“Cheekwood is a local and national treasure filled with stories, local lore, art, gardens and tradition,” she says. After years of visiting, Deby and Keith began to attend the Swan Ball in the early 2000s. In 2008, Deby deepened her involvement with the estate by joining the board.

Cheekwood is known as one of the great examples of American Country Place Era estates. Throughout the year, the historic site hosts art exhibitions, tours, concerts, and special events, including cultural celebrations like Holi, Black Arts Bash, Otsukimi (moon viewing), and Día de los Muertos. Cheekwood also welcomes more than 13,000 schoolchildren to its grounds annually — at no cost.

While leadership, diversity, legacy and, of course, strategic planning are all central to Deby’s work at Cheekwood, she says this “focus on serving our entire community” is an especially important part of the job.

Known for her passion for gardening, Deby also serves as president of the Horticultural Society of Middle Tennessee, an organization that operates out of and benefits Cheekwood, further strengthening her connection with the estate. HSMT helped establish Cheekwood in the 1960s when the Cheek family gifted the estate to the people of Nashville. Over the years, Deby has worked tirelessly to support both organizations — not only as a board member, but also as a committee chair and avid volunteer.

“Deby’s commitment to Cheekwood is unwavering, and her passion for the institution is evident in everything she does,” says Jane MacLeod, Cheekwood's president and CEO. “Her impressive generosity and gifts of time and talent have made a lasting impact on the institution, helping to shape Cheekwood’s future for years to come.”

Dress: Teri Jon by Rickie Freeman floral silk-linen fit-and-flare midi dress (Gus Mayer)

Shoes: Girotti custom purple suede slingback pumps: (personal collection)

Earrings: Gold mirror-back crystal earrings (personal collection)

Necklace: Gold and aquamarine necklace (personal collection)

Bracelet: Elizabeth Locke gold and gemstone cuff (King Jewelers)

Florist: FIORELLA Nashville