LEGACY IN STYLE: A Burlington retail family evolves through mentorship and community pride

Joelle Cooling has fostered a collective spirit from the day she opened the doors to her successful downtown Burlington fashion boutique, Joelle’s. A deep-rooted connection to giving back, whether through volunteering, fundraising, charity work, or mentorship, was ingrained in her early. At age nine, Cooling got her first taste of hard work at her best friend’s family greenhouse, as helping out was the only way to hang out. That experience would help define her career as an entrepreneur.

A New Chapter

Cooling recently retired from ownership of Joelle’s after 28 years. Her legacy will continue through three local businesses, each playing a role in reimagining the retail scene. This unique transition, happening at a challenging time for independent retailers, is a refreshing evolution for Burlington’s downtown core. It includes the launch of Joelle’s By Ally on John Street; the expansion into Joelle’s former Brant Street location of Jeff’s Guyshop, run by her husband Jeff with their son Jackson joining the team; and the arrival of ROAM, owned by Alex Brooker and Erica Gower, both former Joelle’s employees, in the previous Jeff’s Guyshop space.

“You’ll still see me working at Joelle’s by Ally on occasion or over at the men’s store,” Cooling says. “The relationship with my customers is so valued and never forgotten.” 

The evolution of retail

Cooling is transparent about her reason for retiring: burnout. After navigating the pandemic, keeping pace with the constantly changing digital world, and feeling physically exhausted, she wants others to know they’re not alone if they’re feeling overwhelmed. “I’m giving myself a break so I can be the best me again,” says Cooling. “My focus is wellness, and wellness for me includes the business.”

A series of serendipitous events led to ensuring the right person would carry on her business. This person turned out to be Ally Reed. “Her dad shopped at our store and always spoke so highly of his daughter,” she explains. “Ally had always dreamed of opening her own business, and I agreed to mentor her for a year and then continue the discussion about ownership.”

Soon after the doors closed at the original Joelle’s location, Joelle’s By Ally opened on February 10, 2025. “Moving to a new space gave us the opportunity to reimagine the already successful brand,” shares Reed, new owner of the boutique. “It was important to me to design a space that still felt authentic to the old store but with my twist on it.”

After a complete renovation, Jeff’s Guyshop reopened on March 1, offering a revitalized shopping experience in a bigger space. “We have created a hub downtown with the three businesses,” says Jackson Cooling. “All of the stores are on the same block and have the same familiar faces our customers have grown to love over the years.” 

As the new shop on the block, ROAM also opened on March 1. “We get to build our following and continue to help customers we’ve known for the many years we worked at Joelle’s,” adds Gower. “We’re excited to put our spin on a new boutique experience and style sense.” 

Tailoring the future

Beyond business planning and logistics, the transition underscores something even more important – having someone who believes in you. “Joelle has mentored me about the importance of our customers and providing exceptional service,” says Reed. “Her dedication to the community and her passion for business gave me the confidence to continue Joelle’s business forward.”

“Joelle’s unwavering support helped get us here. We grew our friendship as her employees, and she remained our mentor and role model,” explains Brooker. “She encouraged us along the way and offered us the space to expand our permanent footprint in downtown Burlington.”

Jackson Cooling echoes the sentiment. “I’m looking forward to continuing the legacy of the business my parents started,” he says, “but also adding my personal touch on things to welcome the next generation of shoppers.”