Good Time Hat Line

Sarah Chestnut’s hats are inspired by people, places, music and stories—what she calls “the crazy stuff of life”—but each one carries with it a hope and a prayer that the wearer will not only have a good time wearing it, but that he or she will also be blessed by it.

article by APRIL CLARK HONAKER | photography by KELLY MOORE CLARK
styling by BRANDI BROWNLEE HOWARD

SINCE SHE WAS A LITTLE GIRL, Sarah Chestnut has had a mind for business. When the desire to sell grew strong enough, she started peddling her mom’s silverware to neighborhood children. She charged 25 cents a spoon, and each one came with the promise of adventure. “We were digging to China,” she said. Although Sarah’s mom Denise wasn’t thrilled with her daughter’s first entrepreneurial venture, she and Sarah’s dad, David, have been Sarah’s biggest supporters ever since. In fact, when Sarah started an organic egg business before she was licensed to drive, her parents allowed her to use the car for the sole purpose of delivering eggs. They only put their foot down when her client base expanded beyond the city limits.
In the process of launching and growing her egg business, Sarah learned many of the things needed to launch her current endeavor, Good Time Hat Line. When she was getting her feet wet, Sarah’s parents required her to write a business plan and keep track of every transaction. In fact, she said her dad Dave was like Dave Ramsey before Dave Ramsey was even popular. As a result, she grew up learning about money and all the behind-the-scenes aspects of business. But in addition to learning about money, Sarah was learning about people. She grew up in Natchez, Mississippi, and went everywhere with her mom, which meant that her mom’s friends became her friends. According to Sarah, Denise and her friends were an eclectic group that included a strong Christian, a gypsy, an outdoorswoman, and Denise herself, a southern belle. Sarah is thankful for the diversity of this group and said, “I’m a mixture of all those people.” Because of that mixture, she seeks out diversity in her friends and can relate to people from all walks of life.

Sarah’s upbringing ultimately created a woman with a clear focus. “When I look at the world, I see business and people,” she said. Since graduating with a Bachelor of Science in fashion merchandising from Louisiana Tech University, Sarah has worked to connect her passion for business and people through hats. Hats have been a part of who she is since she was a child wearing a little red hat and navy coat everywhere. The ensemble made her look British, and the effect was so strong that people would speak to her in a British accent.

When she got older, she continued to wear hats and had a particular green hat that would spark conversation and garner compliments. She also worked at a western store while in college and enjoyed watching the range of people choose hats. Sometimes a frat boy and a farmer would choose the same hat, and that hat might be the only thing they would see eye to eye on. These experiences have shown Sarah that hats have the power to bring people together. “I love how hats break through every age, every race, every stereotype,” she said. Some people were made to wear hats, and according to Sarah, “They’re the exclamation point, and the hat’s the dot.”

But at the same time, some people don’t think they can pull off a hat. Sarah hopes her hats can break barriers for both types of people. She hopes her hats connect people that might not otherwise be connected and that her brand will encourage people to grow and expand their horizons. “Don’t wear a hat unless you want to be talked to,” she said. “If you’re moving to a new town, buy a hat.” Sarah hopes that when people put on her hats, doors will be opened in their life. “That’s literally what I pray for,” she said. “When sewing them, I pray for the person who’s going to wear the hat with every stitch, so it is about hats for me, but it’s more about what the hats represent. I want this brand to be about all kinds of kinds.”

Sarah not only prays for her future hat wearers. She’s prayed over her business from the moment it was conceived. The idea came to her during a particularly dark time in her life—a time when she said, “I literally had to sit still for eight months.” In the mornings, she would go to the coffee shop and try to focus on her studies, but she couldn’t. She said, “I couldn’t study, because I kept thinking about these hats.” During this time in her life, it was hard for Sarah to see or hear God. “Sometimes you feel like your life is so rough that you can’t pray about yourself, but you can pray about something else,” she said. “I could pray about the hats.”

From the beginning, Sarah wanted to make sure her hats were manufactured in the U.S. When she was growing up in Natchez, one of the local mills closed. Afterward, she witnessed the fallout as many families lost their livelihood and several were forced to move. As a result, supporting families here in the U.S. was important to her. Over several months, she prayed that God would connect her with the right person. When she finally convinced a man she called “the hippy hatter” to meet her in Dallas, her world changed. “Walking into the meeting was the first time I felt God again,” she said. Even though it had been difficult to feel separated from God for so long, she said, “The cards I was dealt—I had to have those, because I wouldn’t have sat still for anyone else. When I walked into that meeting, the cards were shuffling.”
When Sarah and the hippy hatter met for the first time, he greeted her with a laugh, which immediately diffused her nerves. According to Sarah, after she’d made her pitch, “He said, ‘This is ridiculous, but I’m old, and I need a little fire around here. Because I’m gettin’ bored and I need some young blood, I’ll take you on.’” He’s definitely proven to be the right person for Sarah and her hat line. “I can send him the craziest idea, and we’ll make it together,” she said. “I wouldn’t want to work with anyone else. He’s really the best.”

Through this experience, she’s learned a big lesson. “Even when you’re going through the roughest time, and you can’t feel God, and you feel like He’s put you on the back burner, He may be orchestrating something great. I see that now,” she said. “It’s been the absolute biggest blessing, and I’ve met the best people. If the Lord puts you still, it’s not the worst thing that could happen, because He’s gonna make it worth your while.”

In addition to the hippy hatter, there have been a few other key players in helping Sarah get her hat line off the ground, and she’s prayed for them, too. “I wanted it to be God’s timing and not mine,” she said. “I had everything ready, and God sent me Spencer.” Sarah met Spencer Berry four years earlier around 2 a.m., while duck hunting in Russell Sage. At the time, she had no idea he would later play a role in her business. The two reconnected in January of this year, and Sarah learned that Spencer had started his own marketing business. He understood her mission, and she knew he was the right person to take on the marketing for her hat line. “He’s the only person I’ve ever met that loves people the way I do,” she said.
Around the same time, two other incredible people reached out to Sarah: Rachel Lee and Rhett Parker. Both were photographers with similar visions, and it was like the stars aligned. Because their parents knew each other, they share the same interests, and they were both born at the same time in the same place, Sarah calls them “the constellation twins.”

Of her team, Sarah said, “We’re all night and day different, but we all have the same goals, and we all appreciate diversity.” It’s not uncommon for Sarah and her friends to jump in a car, spur of the moment, to drive to Dallas, New Orleans or some other city, to do a photoshoot with random people on the street. “We’re a rolling circus,” she said. “I knew I had a circus. I just needed the right people to join, and they make life more fun.” When they get together, a good time is inevitable, but that’s not the whole story behind Sarah’s decision to call her brand Good Time Hat Line.

She originally planned to call it Chestnut & Co. but had a lingering feeling that the name was too boring. She wasn’t completely committed to it when she and her team took a trip to New Orleans for a shoot. During that trip, they had planned to get photos of 11 one-of-a-kind hats. While out on the streets, they matched one of the hats with a middle-aged New Orleanian. The woman was game to have her portrait taken but told Sarah, “I gotta finish rolling my joint. Then we’ll take this picture.” Tickled, Sarah looked at her and said, “That is a good time!”

It’s something Sarah has always said about anything that gives off positive vibes—from a cup of coffee to a ripped-up, acid-washed jean jacket. “It’s my number one adjective,” she said. Fortunately, one of her friends picked up on it and suggested she use the phrase as her brand name. After trying it out and seeing how it rolled off the tongue, Sarah agreed, and Good Time Hat Line was born.

Another important factor in establishing her brand is its logo, which is a full moon. The moon and its phases have special meaning for Sarah. When she was growing up, her cousin Anna Rose used to pick on her, saying she was like the moon, because she went through so many phases. The description fit, and Sarah has continued to identify with it. In fact, there was a point in her journey when she believes God used the phases of the moon to send her a message. She was still in the midst of trying to figure out if she should pursue the hat line, when she received a gift from her dear friend, Faith Green. Faith had painted the moon in all of its phases and gave the series to Sarah. “When I opened them up, it was like a slap in the face,” she said. “God did have his hand in this. I just didn’t know it.” Now when she wakes up every morning, the phases of the moon are the first things she sees, and she finds inspiration there.

When Sarah meets her long-term goal, Good Time Hat Line will merely be the first in a series of businesses represented through logos based on the phases of the moon. “This is the one I want to be able to learn everything with,” she said, “but I hope when I take my last breath I have multiple businesses.” Sarah wants an empire, and she’s not afraid of the work it will inevitably take to build it. One of her favorite quotes reads, “Opportunity is missed by people, because it’s dressed in overalls and looks like work.” Sarah believes people often think a career in fashion is all about the shows, but it’s not. She said, “I’ve slept on the floor many a night to be inspired by a cool place and to be inspired by the hats. You make a lot of sacrifices, but look at all the opportunities I’ve gained through all this hard work.” She attributes this lesson to Bill Hammond, a man she calls “the Sundown legend.” “Mr. Bill can teach you everything about life you ever needed to know,” she said, “and he doesn’t even know it.” But Sarah is also the type to look for lessons everywhere. “With everything, you have no choice but to learn, and that’s my goal. I want to learn something every day,” she said. “To see God, I have to go see the world. I have to go see people. I’m always looking for inspiration.”

Sarah’s hats are inspired by people, places, music and stories—what she calls “the crazy stuff of life”—but each one carries with it a hope and a prayer that the wearer will not only have a good time wearing it, but that he or she will also be blessed by it.