Bootmaker of the Stars

American Artisans, People
on September 25, 2005

Hang around Bo Riddle’s small boot shop in Ozark, Mo. (pop. 9,665), and you’ll catch him singing while he stitches. Sometimes it’s a customer’s hit song, and sometimes it’s his own.

“I do my best songwriting when I’m working,” says Riddle, 49, who’s renowned for his custom-made cowboy boots. Among his well-heeled clientele are country singers Marty Stuart, Alan Jackson, Kenny Chesney and Tom T. Hall. Riddle’s shop walls are filled with a who’s who of country music stars’ publicity photos, posters and thank-you notes, ranging from Dolly Parton’s appreciation for a boot repair to Kix Brooks of Brooks & Dunn praising, “Bo, Great Boots Dude!”

Riddle’s boots—with inlaid and overlaid designs of flags, guitars, hearts, flames and other flourishes—have starred in coffee-table books and have been featured in an exhibit at the George Bush Presidential Library and Museum in College Station, Texas (pop. 67,890). But usually, they just help singers tap and stomp out songs about heartache and hope.

“I won’t buy a pair of boots from anyone else,” says Troy Gentry of the country duo Montgomery Gentry.

“Bo came out while we were rehearsing in Nashville and made drawings of our feet,” Gentry adds. “They’re the most comfortable pair of boots. They fit like a glove.”

Riddle began wrestling leather at age 12 after his dad swapped a pickup truck for a shoe repair shop in Willow Springs, Mo. (pop. 2,147). The two learned shoe and boot repair together, then Riddle took boot-making courses at Oklahoma State Technology College in Okmulgee (pop. 13,022). All the while, he wrote songs and played in country bands.

“I wrote my first song when I was 12,” he says. “It wasn’t much, but it was a song—something about falling in love with some little girl and getting dumped.”

Riddle’s passion for songwriting inspired him to open a boot shop in Brentwood, Tenn. (pop. 23,445), near Nashville in 1990. Almost overnight, he was discovered—for his boots. Kix Brooks, an up-and-coming artist at the time, ordered a flashy pair of black boots decorated with red flames, and Riddle’s reputation spread like wildfire. Singer Marty Stuart ordered a pair, and other country stars followed in his fancy footsteps.

In 2004, family ties prompted Riddle’s move back home to Missouri, where his business hums with local customers. Prices for basic custom boots begin at $600. Exotic hides, designs and even company logos kick the price up to $5,000. Riddle expects that a well-kept pair of his boots can last up to 20 years.

His craftsmanship is seen in every step, from the original designs to the perfect rows of stitches that he guides under the sewing machine. He often spends up to 100 hours on an intricate pair of boots.

“You can get as crazy and elaborate as you wish,” Riddle says. “Making boots is an art form, and I’ve always been artistically gifted.” As an asthmatic child, he often stayed indoors, where his mother taught him to sew at age 5. Plus, boot making is in his genes, he says. His great-grandfather made boots during the Civil War.

Riddle says his success as a boot maker foots the bill for his other artistic love—songwriting. He’s written more than 150 songs, which he pitches to artists and music publishing companies. In 1996, Riddle even released his own album, A Song to Boot, on Voyage Records.

“Marty Stuart told me, ‘We have a lot of good songwriters, but not many good boot makers,’” he says. “In so many words, he said, ‘Shut up and be happy.’”

Riddle laughs, then sets aside the boot he’s building to take a break with his guitar. Amidst a backdrop scent of freshly tanned leather, Riddle belts out one of his original songs, titled Last Chance, Oklahoma.

Stomping his feet in his ostrich-skin boots, he looks and sounds every bit a star.

For more information on Bo Riddle’s boots, call (417) 582-2668.