Anne BildHow Caryn O’Sullivan of Drapery Street is redefining the window treatment experience—one detail at a time
Caryn O’Sullivan never set out to build a typical design business. When she launched Drapery Street in 2006, her mission was clear: to reinvent the window treatment shopping experience by making it interactive, consultative and enjoyable—far from the transactional, overwhelming process it so often is. Nearly two decades later, that mission still guides her work, as she leads a thriving woman-led company based in Carmel, Indiana, with two showrooms, an in-house workroom and a tight-knit team of 18. The name Drapery Street came to Caryn during brainstorming sessions with peers and mentors. She had initially considered “Draped,” but Drapery Street struck her as a better fit—an identity that could grow with her business if she ever decided to branch into other offerings like “Bedding Street” or “Pillow Street.” Over time, the name took on an even more playful meaning: fabrics began being labeled by their “Street name,” creating a signature Drapery Street experience for clients. While the company’s early focus was on custom draperies, Caryn and her team soon expanded their mastery to hard treatments, window film and outdoor shades—allowing them to treat the whole home, not just the window, in ways that matched each client’s lifestyle, budget and aesthetic.
“Our strategy for growth isn’t rooted in growth for growth’s sake—it’s centered on excellence”
Building a Business from the Ground Up
Armed with an MBA in finance and a background in startups and accounting, Caryn brings a distinctive blend of analytical thinking and creative problem-solving to the world of custom window coverings. Though she’s dabbled in adjacent categories like wallpaper, furniture and upholstery, she’s always drawn back to the complexity and potential of window treatments. “There’s just so much opportunity for innovation in this space,” she said. “I learn something new every day.” That spirit of constant curiosity has shaped Drapery Street’s approach to growth. Rather than scaling rapidly, Caryn aims for a steady pace of 10 to 15 percent each year—fast enough to build momentum but slow enough to protect the client experience. “Our strategy for growth isn’t rooted in growth for growth’s sake—it’s centered on excellence,” said Caryn. That philosophy of doing things the right way, combined with a focus on delivering an exceptional client experience, has fueled the company’s long-term momentum.
“There’s just so much opportunity for innovation in the [window treatment] space. I learn something new every day.”
Helping Clients See the Difference
While Instagram plays a key role in telling Drapery Street’s story and showcasing standout projects, Caryn believes the company’s greatest strength lies in its ability to simplify a complicated process. That includes breaking down what “custom” actually means. “That’s a big question. ‘Custom’ really exists on a spectrum. At the highest level, true custom means creating something for the first time that is entirely unique. This kind of work requires deep expertise, creative problem-solving and a highly skilled team to execute successfully,” she explained.
That consultative approach also extends to educating clients about product quality. Caryn often finds herself walking clients through the significant differences in construction, materials and performance—especially when it comes to motorization. She’s a firm believer in automation and calls it her favorite trend. And while she’s thrilled that color and pattern are making a comeback, there’s one trend she hopes stays in the past: “I’m not ready for swags to come back,” she laughed.
In addition to interior projects, Drapery Street has expanded into outdoor shading, treating exterior spaces with the same level of precision and customization. Caryn sees it as a natural extension of the home and encourages designers entering the category to think holistically. “You have to consider sun exposure, wind, insects—every site has its own challenges,” she said. “But if you approach it thoughtfully, you can create something really special.”
Leading with Heart
For Caryn, that attention to detail is about more than design—it’s about building something lasting. She credits much of her leadership mindset to Brené Brown’s “Dare to Lead,” which reinforced her belief that strong leadership is a learned skill rooted in vulnerability, courage and trust. It’s a philosophy that shapes the supportive culture at Drapery Street, where team collaboration and client care go hand in hand. That doesn’t mean Caryn doesn’t have fun along the way. (She had an Elvis impersonator at her wedding, after all.) But she’s serious about the role Drapery Street plays in her clients’ lives—and the joy she feels watching it grow. “This industry has so much to offer,” she said. “And I’m grateful I get to keep evolving with it.”
Backyard Bliss
This Carmel, Indiana, project proves that customization is everything. Working with builder Christopher Scott Homes, architect Emily Handke Design, integrator Intelligent Living and designer Kara Grider, Drapery Street crafted custom outdoor shades that deliver the best of both worlds: privacy without sacrificing the view. By adjusting the openness percentages between the side and center screens, Caryn and her team tailored the porch to fit exactly how the family lives, entertains and relaxes.
Article by Lindsay Brown
Window Fashion VISION Editor
This article is originally featured in the May/June 2025 issue of Window Fashion VISION HERE.
