PaperCity Conversations — Dynamic Cowboy Boots Entrepreneur Had Courage and a Guardian Angel on Her Side

Working a high-level corporate job, Lizzy Chesnut Bentley felt stifled. She had the big title and the big responsibilities, but something was missing. Something creative.

“I started really as a concept just to keep myself sane,” Bentley tells editor-at-large Francine Ballard in our latest edition of PaperCity Conversations. Bentley is talking about the humble beginnings of her now burgeoning CITY Boots brand. A little girl who never wanted to take off her pink cowboy boots as a kid would become a self-made businesswoman who built her own sophisticated cowboy boots and Western brand.

A lot of people feel held down by their corporate job. Lizzy Chesnut Bentley showed the courage to do something about it. With the help and endless encouragement of her late husband/guardian angel William Bentley.

“He was instrumental in getting it to the point where I could provide for myself,” Lizzy says.

“He’s your angel,” Ballard replies.

“He just totally believed in what I was doing,” Lizzy says.

William Bentley died suddenly at age 37 due to an undiagnosed medical condition in April of 2019. Lizzy Chesnut Bentley found herself a young widow with a relatively new company. She’d rely on what she knew best.

“I have always been a cowboy boots girl,” Lizzy says. “I’m from Amarillo, Texas. I was that little girl in pink boots who wouldn’t take them off. I made my dog boots when I was four years old. It’s just kind of a family thing.”

That’s just a snippet of the latest episode of PaperCity Conversations, a new regular video series that showcases interesting conversations with fascinating figures. Ballard has a way of getting compelling people to open up and while Lizzy Chesnut Bentley’s story has been told before, this is different. This is a chance to really see the determined woman entrepreneur behind this unconventional boots and Western brand. And understand what drives her.

Lizzy Chesnut Bentley started CITY Boots because she saw really nothing like it in the marketplace — direct-to-consumer cowboy boots with a little luxury cache. She remembered how fascinated the out of state girls you went to school with at SMU were by nice, girl friendly, cowboy boots.

“There wasn’t a great option for professional cowboy boots for women,” Lizzy tells Ballard.

CITY Boots has grown into a largely online business and Lizzy Chesnut Bentley, who lived in Houston for a while, went to school in Dallas and grew up in the Texas Panhandle, now calls Fort Worth her home and base of operations. But these boots travel. Bentley spends a week at the Houston Rodeo every year, holds shows at places like Bering’s — the iconic Houston store that traces its roots back to 1940 — and The Forrest Club.

Ballard interviewed her in Molly Montgomery’s striking Memorial home. Another setting in which Bentley’s cowboy boots fit right in.

The love for cowboy boots — even in a corporate setting — are not going away. “There are so many times a cowboy boot is your most important accessory,” Ballard notes.

Lizzy Chesnut Bentley goes on to tell the story of how a podcast helped shape her business plan in this exclusive PaperCity Conversation. Want to hear the whole story?

Watch the full conversation in the video player above this story — and look out for a new episode next week.

Credits for Video: Jenny Antill Clifton