Legend, whose real name is John Stephens, helped his dad today sell the hats at the 2014 Ford Neighborhood Awards in Atlanta.
Stephens, from Sprinfield, Ohio, said he first began putting different hats together to wear himself.
He took an old straw hat and cut off the brim; he then attached a baseball cap's brim, which he encased in black leather, the Springfield News-Sun reports.
"As Ron remixed each hat and began sporting them around town, family and friends were so impressed they began encouraging him to take them to the marketplace," the Popz Topz website states.
Stephens started Popz Topz LLC in January 2012 with a business partner, the site states.
"The mission was simple. Create a look for men, women and the up-and-comers that are avant-garde, appealing, adaptable and affordable," Popz Topz website says.
The wool felt hats are listed for $85 online and the straw hats cost $139.