Entering Nashville’s new men’s clothier Simon Says is like stepping into a treasure trove of stylish, high-quality pieces. Settled in Wedgewood-Houston, the shop tastefully curates pieces from designers who intertwine their stories into their clothing.
At Simon Says, fashion and comfort are equally crucial. Customers can expect to find one-of-a-kind items that are also comfortable and durable. “I want people to have access to things that they haven’t heard of and that they’ve never seen before,” says Stephanie Simon, the shop’s owner and founder. “But I also want it all to be wearable.”
Drawing inspiration from cowboy culture and rock ’n’ roll, the store is geared toward the distinct style of Nashville men. “Nashville reminds me of New York and LA,” Stephanie says, “not just because people are hustling and doing the thing, but because they want to look good while doing it.”
Simon Says was designed to reduce shopping anxiety. Every aspect of the experience flows with ease. Since the store’s November opening, its guests have been greeted with natural lighting, cozy rugs, plush couches and the friendly faces of Stephanie, chief operating officer Andy Burns and in-house hatmaker Jacob Hillenbrand.
Before entering Nashville’s fashion scene, Stephanie did design, management and brand promotion for the legendary San Francisco Western shop H Bar C Ranchwear. She also dressed musicians — including Robert Plant, Marcus King and Midland — for red carpets and award shows. “When we met Robert, we had just remade a shirt that he had worn onstage in the ’70s all the time, and he walked into the store,” she says. “I don’t normally fangirl, but I immediately knocked over my cup of tea.”
These musicians eventually became family. “You watch them fly, and your heart is so happy for them,” says Stephanie. “And seeing them proud of me is a freaking trip.”
When Stephanie moved to Nashville, she began working at the renowned boutique Two Old Hippies. After the COVID-19 pandemic, she noticed gaps in the local fashion industry — namely, the slim selection of high-quality menswear stores. In true do-it-yourself fashion, Stephanie decided to fill that space — spearheading every part of the process, from construction to curation. “I didn’t think I could accomplish this, and I did,” she says. “It’s been probably the most joyful thing I’ve ever done.”
She took her vision for Simon Says to the next level by featuring high-quality brands and designers whose work sparks vivid memories for her. A signature John Varvatos T-shirt takes Stephanie back to when she’d just moved to Nashville, and custom embroidery by the mother-daughter duo Dixon and Jack — worn at major concerts and award shows around town — reminds her of how much she loves working with her mom. United Rivers exemplifies the power of storytelling through clothing. The brand, owned by Colombian immigrants, visually combines Colombian cowboy culture with that of the American South.
“It does take a village to do anything, and I would have been a lot more stressed-out if I didn’t have the team that I have,” says Stephanie. “Even the contractors, my designers, all of them — everybody has a value that is indescribable.”
The store’s staff is known for being refreshingly honest with customers, and they’re the first to celebrate when guests find pieces that make them feel their best. “Some people just don’t realize how much they need that little boost of confidence,” says Stephanie. “And it’s not even me giving it to you — it’s the clothes doing it. I’m just reiterating what the clothes are doing.”
Stephanie’s adoration of every item in the shop is evident, and her passion for improving the shopping experience propels her forward. “When somebody walks out with a smile on their face, it’s like you just finished your second dirty martini, and you’re like, ‘Yeah. Now, that’s the good stuff,’” she says.
