The Boots That Wouldn’t Break In

How musician Bob Livingston’s one and only pair of Charlie Dunn boots ended up at Goodwill.

By Joy DiazJune 21, 2017 12:50 pm, ,

We’ve been asking Texans from all walks of life to talk about their favorite boots. Texas singer-songwriter Bob Livingston heard the first installment of our “From Heel to Toe” project and shared an unforgettable story about his pair of Charlie Dunns.

Livingston saw his first Charlie Dunn boots in Los Angeles when he went to see Jerry Jeff Walker perform.

When Walker sat down to play, his pant legs came up and “revealed the coolest boots I’d ever seen,” Livingston says.

“They were embossed on the front with this big JJW, obviously handmade,” he says. “I had a pair of boots, but nothing like this.”

Livingston found out that the boots were made by legendary Texas bootmaker Charlie Dunn.

“It wasn’t long before he was an international celebrity, literally, because of a song that Jerry Jeff wrote called ‘Charlie Dunn.’

“It makes Charlie real pleased to see me walking in these. Charlie Dunn, he’s the one to see.”

Livingston saved up for a pair, which he purchased at Austin’s Capitol Saddlery in 1972 for $400. He joined the ranks of Texans like Lyndon B. Johnson and Darrel Royal who also owned Charlie Dunns.

But no matter what he did, he couldn’t break them in.

“If I ever wore them on stage, oh my goodness, I couldn’t even finish the set practically,” Livingston says. “I had to take my boots off, the arch was sticking up there.”

So he retired the boots to the back of his closet.

“I think back all these years later and I wonder why didn’t I go back and just really talk to him about it,” he says. “It was like going to the pope and asking for a different prayer. He was so mysterious… he was the guy who was supposed to be the world’s greatest craftsman and everything, and I didn’t want to call him on it.”

The boots would have stayed on his closet floor, had it not been for Livingston’s wife. She inadvertently donated them to Goodwill when she was cleaning out the closet.

“Whoever bought them for five bucks, never knew what he had,” Livingston says.

Now, Texas, it’s your turn. Tell us a great story about your boots so we can share boot stories from across the state. You can get in touch by emailing