Bailey Boys is a family-owned children’s clothing company rooted in Southern tradition, timeless style, and the belief that childhood should be celebrated.

Today, Bailey Boys is led by Chad and Rachel Bailey, who purchased the company in 2018 after years of working side by side within the business and continuing the family legacy into a new generation.

Chad Bailey joined the family business in 2001 after graduating from Georgia State University with a degree in finance and spending several years working in business and real estate. Growing up around the company, Chad developed an early appreciation for entrepreneurship, customer relationships, and the values Bailey Boys was built upon.

Rachel joined Bailey Boys in 2008 and quickly discovered both a passion and talent for the business. Having grown up along the Georgia coast, Rachel brought a natural love for classic Southern style, timeless children’s fashion, and the moments that make childhood special. What began as a role representing Bailey Boys as a sales rep quickly evolved into a much larger creative role within the company. Today, Rachel continues to oversee sales relationships across the country while also collaborating closely with the Bailey Boys head designer and creative team to help shape the collections and creative direction that define the brand today.

Chad and Rachel both grew up in the Golden Isles and met on St. Simons Island after college. They married in 2004 and have built both their family and business together on the Georgia coast ever since. Today, family life, coastal living, traveling together, and creating lasting memories continue to inspire the spirit of Bailey Boys. Their two dachshunds are just as much a part of daily life and the family business atmosphere as everyone else.

While Bailey Boys has evolved over the years, the company’s foundation remains deeply connected to its beginnings.

The brand was originally founded in 1987 by Chad’s mother, Diane Bailey, whose passion for timeless children’s clothing inspired the creation of the iconic Bailey Boys John-John. As the original Bailey Boys designer, Diane became known for her creativity, attention to detail, and signature appliqué designs that helped define the look of the brand for generations of families. Alongside her husband, Jim Bailey, what began as a five-sewing-machine operation in a room no larger than an average bedroom grew into one of the country’s most recognized names in classic children’s clothing.

Jim’s entrepreneurial spirit and belief in the brand helped turn Diane’s early designs into a growing family business. Years later, the J. Bailey lifestyle brand was created and named in his honor by his sons — continuing the family story and honoring the values on which the company was built.

Today, Bailey Boys serves more than 300 boutiques and retailers across the United States while remaining proudly family-owned and operated. The company continues to operate a 22,000-square-foot manufacturing facility in Baxley, Georgia, where craftsmanship, attention to detail, and Southern tradition remain at the heart of every garment.

From its headquarters on St. Simons Island, Bailey Boys continues to design, ship, and inspire from the same coastal community the Bailey family has called home for generations. The company’s corporate offices, shipping operations, and flagship retail store all remain on St. Simons Island — a place whose charm, warmth, and relaxed Southern lifestyle continue to influence the brand today.

For Chad and Rachel, Bailey Boys is more than a business. It is a family legacy, a creative passion, and a commitment to creating timeless children’s clothing families will treasure for generations.