Sissy Light was never supposed to be a hat company. At least, not at first.

Really, it was just an excuse to get back to Round Top.

If you’ve ever spent a spring or fall wandering those fields, you can probably understand why.

Just ask founder Kristin Light, whose love affair with Round Top began long before she ever thought about designing a hat.

Funny how things work out.

A Little Round Top Magic

Today, Sissy Light is known for its straw hats, signature cords, and effortless silhouettes that have found their way from the fields of Round Top to women across the country.

But long before Kristin was designing hats of her own, her best friend, Katy Bader, invited her to come help at her first show at Bader Ranch.

“I remember driving in after dark with absolutely no idea where I was going,” Kristin recalls.

There was hardly any cell service, Katy wasn’t answering her phone, and then, seemingly out of nowhere, Kristin spotted a barn glowing with party lights. Inside, a handful of people were gathered, and Katy was floating around in a flowy dress, looking perfectly at home.

Something about that night stuck with Kristin. She’d planned to stay for a day, but after driving home for one of her kids’ activities, she turned right back around.

“I think I knew almost immediately that I wanted a reason to keep coming back,” she says.

Then Came the Hats

It was the spring of 2017, during Katy’s very first show at Bader Ranch, when a group of women wandered into the barn for coffee wearing simple straw fedoras.

At the time, hats weren’t quite the Round Top staple they are today. But Kristin and Katy loved what they saw, and by the time summer rolled around, the two friends had made it their mission to find some of their own.

They looked everywhere. In stores, while traveling through Europe, anywhere they thought they might find the perfect straw hat. But nothing was quite right. There were limited styles, even fewer sizes, and nothing that felt like what they had in mind.

Their search eventually led them to New York, where a last-minute trip turned into meetings with three hat designers. Kristin borrowed money from her mom and spent around $8,000 on their first order.

By the time the fall show came around, Kristin was ready.

Her dad had helped her build large hat display walls, which she dressed up with wallpaper and filled with straw hats in different silhouettes, sizes, and styles. It was something a little different from what shoppers were used to seeing, and they responded.

“I never left the barn that show,” Kristin remembers.

She was determined to make her money back, and by the end of the show, she’d sold almost everything.

For someone who’d originally come to Round Top just to help her best friend, she suddenly had a reason of her own to be there. Without quite realizing it, the beginnings of Sissy Light were already taking shape.

The Hats That Started It All

As the shows went on, Kristin started running into a problem that anyone who’s spent a fall afternoon in Texas can probably understand.

The weather wasn’t exactly keeping up with the fashion calendar.

While the designers she bought from were moving into their fall collections, Round Top was still seeing temperatures close to 100 degrees. Her customers wanted straw hats, but by September, they were becoming harder and harder to find.

Kristin started buying extra inventory in the spring just to have enough for the fall show. Eventually, she realized that if she wanted to keep offering the hats her customers loved, she was going to have to make them herself.

Her first design was inspired by a straw hat she’d found during one of her family’s summers in San Miguel de Allende. Her mother-in-law had discovered a beautiful hat at a local artisan market, complete with a thick leather chin strap, and Kristin had loved it enough to buy one of her own.

That silhouette became the inspiration for the Sissy Hat, which is still part of the collection today. Kristin was particularly intentional about the fit and the taller crown, a silhouette she wasn’t seeing much of at the time. That higher profile, along with natural, textured materials like seagrass, would go on to influence the designs that followed.

But rather than make a big announcement about designing her own hats, Kristin decided to bring a handful of her designs, hang them up, and see what happened.

“We didn’t announce that the hats were ours. We didn’t even put labels inside them. We’d simply make a handful, hang them among all the established designers on the wall and see what people reached for,” Kristin tells us. “Almost immediately, girls were choosing ours.”

For nearly two years, Round Top became Kristin’s testing ground, with shoppers helping shape a collection they didn’t even know was hers.

It was an education in what women actually wanted to wear, happening right there in the barn. Little by little, those early experiments were becoming a collection of her own.

Growing Up in Round Top

“I’ve always said Sissy Light grew up in Round Top,” Kristin says.

In fact, some of the brand’s most recognizable details can be traced right back to those early shows.

Take the signature hat cord, for example.

“I’m not out on a ranch riding horses or anything,” Kristin says. “But I am traipsing through the fields and tents and the weather here is no joke.”

Between the wind and the miles of walking, Kristin wanted a hat she could wear comfortably all day, even when she wasn’t actually wearing it on her head. The leather cord became a practical part of the design, and eventually one of the details Sissy Light became known for.

As the brand expanded beyond Round Top, Kristin introduced colorful paracord options, bringing a more playful, beach-inspired element to the collection. What began as a practical solution for windy days in the fields became a fashion statement of its own.

“It’s like how many hat cords can a girl have?” Kristin jokes.

Apparently, quite a few. Customers began collecting multiple cords to change up the look of their hats, turning what started as a functional detail into one of the brand’s most recognizable signatures.

The same goes for the collection itself. Years of meeting customers face-to-face gave Kristin a sense of what women were looking for, whether that was a classic natural straw hat or something more colorful and unexpected.

“Our Round Top shoppers were, and honestly still are, our focus group,” she says.

For years, that’s exactly how Kristin approached it. She wasn’t designing collections in isolation or trying to predict what women might want six months down the road. She was standing right there with them, watching what they tried on, what they loved, and what they came back for.

The bucket hat is perhaps the best example. Kristin admits Sissy Light was late to the trend, largely because the brand’s original silhouettes were already selling so well. But when the company finally introduced its own version, complete with the signature hat cord, the response was immediate.

The bucket hat quickly became one of the designs that changed the trajectory of the business. Today, Kristin says shoppers arrive in Round Top with a Sissy Light hat at the very top of their lists, sometimes making it their first stop before exploring the rest of the show.

Eventually, the hats started selling faster than she could keep them in stock. One successful show became another, until what had started as a creative outlet was becoming something much bigger.

“The business almost led me before I led the business,” Kristin says.

By 2021, Sissy Light had launched its first full collection and website. Today, Kristin and her small team ship hats across the country, with designs that have found their way well beyond the fields where they first took shape.

What Follows You Home

It’s funny to think that none of this was really the plan.

When Kristin first arrived at Bader Ranch all those years ago, she had no idea she’d eventually be designing hats, running a business, or shipping her creations across the country.

“We didn’t create a storefront there because we had some big plan to build a brand or generate an income,” Kristin says. “In the beginning, the entire point was to have a reason to get to Round Top.”

Perhaps that’s part of what makes Round Top so special. You never quite know what you’ll find when you get there, or what might follow you home.

For Kristin, it was a whole new chapter. And, of course, a few really good hats.