Navigating rural Texas locales during a stint in oil and gas, Lizzy Chesnut Bentley picked up the nickname “City.” But what many didn’t recognize in the polished, SMU-schooled business boss was the girl who grew up on horses in the cowboy-rich lands of the Texas panhandle. Boots have always been a focal point of Lizzy’s life, practically and expressively. She traded the corporate world for a head-first dive into the heirloom boot world. Now, she’s the head honcho of CITY Boots!
Tell us a bit about your younger years through college.
I grew up in Amarillo, in the panhandle of Texas. It’s a bigger town, but it’s very remote and heavily Western-influenced. My parents are both from even smaller towns nearby, and I grew up traveling that area but always wanting to see the bigger world.
As a child, and even in high school, I was interested in art and took lots of art classes. I remember always wanting crazy hairstyles as a little girl. I was naturally creative and interested in making a statement. I really enjoyed drawing. I chose SMU in Dallas because it had people from all over. It was a very out-of-state school, and that was attractive to me because I wanted to meet different kinds of people.
How did you begin to gravitate away from the corporate world and into fashion?
My fashion journey started with the interest in cowboy boots I noticed at SMU, but I decided to go the business route. I graduated with a degree in finance and a minor in economics. When I started my career in oil and gas, I was always interested in looking cute out in the corporate field. I wanted to dress up and stick out. CITY Boots started as a creative outlet for me and is now my career.
How does the name CITY Boots play into your brand ethos?
“City” was a nickname I had in a more rural setting. It was funny to me because I’m not actually from the big city. But I had obviously adopted some of those styles or markers. It made sense when I wanted to name the brand. I was trying to appeal to that city person and the person who’s been buying boots their whole life.
I do that by simplifying the design to make it more sophisticated and wearable in a fashion setting while staying focused on the product’s heirloom quality and the construction’s authenticity. That was always a city boot to me. It can be on pavement or the ranch, and it fits well in either place.
Your line has it all — from classic styles to spunky. What inspires you when you add a new shape or design to your collection?
When I design my boots, I think about my needs. I always tell people boots are like handbags. There’s not one boot that fits every scenario, so you need your boot for a dressier occasion or professional event. Or you might want a boot for game day or something a little more edgy for a concert. You can do a lot in a cowboy boot. It can be super girly or super edgy, and I like to have a little bit of everything.
The main driver is asking myself, “What do I need in my life?” As I grow into adulthood, I need new things and design around them. In the corporate world, I needed a black, basic cowboy boot that could go with a blazer and not look like a little girl in her Daisy Dukes. Well, now, Daisy Dukes are back! So what do I want to wear with my Daisy Dukes? Hopefully, thinking about my needs means other people need these styles as well.
What’s a day like in the City Boots hive? How many people does it take to run the show?
No two days are the same. As a small business, everyone wears a lot of hats. One day, I could be in our factories and then turn around two days later and be on the set of a photo shoot. I’ll be at an event one night, then hiding away, getting designs out the next day. I’m having a lot of fun right now with the business because I am touching all areas. That’s challenging, but it’s important. So it’s lots of variety, which is fun.
What’s a common misconception people have about bootmaking?
My favorite part of any cowboy boot is the heel — especially of a handmade cowboy boot. That’s not always the most exciting part for people. Many think that the heel and the sole of the cowboy boots are made out of wood, but they’re actually made out of leather.
What’s something that people are surprised to learn about you?
People are surprised I’m from Amarillo, Texas, where the brand’s story is rooted. It’s rooted in my family, our culture, and the love for cowboy boots that my grandparents instilled in me.
Where can we find you on your days off?
I love football season. We go to a lot of games and concerts. I’m always at Ascension Coffee or Maria’s in Fort Worth.
What’s the best advice you’ve received, and from whom?
When I first started the brand, I had just placed my first order and went to New York City with my mom and sister. They were shopping around — I wasn’t, because I was starting a business — and my sister wanted some Stewart Weizman boots. We popped into the Stewart Weizman store, and he happened to be there. My mom, being the cheerleader she is, said, “My daughter’s starting a shoe company!”
He told me, “You’re going to love this business,” which was good encouragement. Then he said, “Fashion is so fun because you get to express yourself, and if you build it, people will come.” So, I continue to build my brand smartly in a way that feels like an expression of myself. It’s great that other people enjoy it, too.
Besides faith, family, and friends, name three things you can’t live without.
My iPad with my pen — I do everything on it. Micellar water. A James Perse basic white T-shirt.
LIGHTNING ROUND
Who else is inspiring you right now? I’m reading Tash Oakley from Monday Swimwear’s new book Exsessively Obsessed, and I am obsessed.
Bucket list vacation destination?: Machu Pichu and Thailand
Favorite “hidden gem” in Texas? Big Bend
What’s on your bedside table? A lamp, a jewelry box, and a book
Go-to birthday present to give? Champagne or cowboy boots
Thank you, Lizzy, for such a fabulous chat!
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