Building Community Through Comfort: The Story of a Dartmouth-Inspired Pajama Brand
How a Dartmouth alum and her sister created a company that gives back
Katie Weber ’24 and her sister Madelyn Weber are business partners and the creative minds behind Sleepy Saturday, a stylish and comfortable pajama brand. We spoke with Katie, Madelyn, and their student ambassador, Olivia Galiatos ’26, about the company, how it came to be, and their experience entering the fashion industry.
Motivated by a desire to do something more meaningful and creative, Madelyn Weber decided to leave her career in investment banking. Drawing from her experience designing t-shirts as a student at Washington and Lee University, she began exploring customized apparel—this time, on a larger scale. For this project, inspiration came from the North, with the idea of highlighting Hanover’s incredible sense of place and community through a design that paid homage to the Upper Valley restaurant scene.
“I loved the restaurant scene in New York City,” says Madelyn, “and I was trying to think of a way to create something apparel-related that encompassed the restaurant community. Then the idea of a connection to Dartmouth came through Katie.”
The concept took shape when she realized that pajamas offered a unique canvas with loads of business potential. “Pajamas are this interesting intersection where you can have fun, cute designs and still be considered high-end. People pay a premium for them,” she says. The simplicity of pajamas was also an appeal. “They’re comfy, baggy, and operationally simple. I didn’t need to be a fashion expert to get into it.”
Madelyn reached out to her sister Katie to connect the product with the Dartmouth community. “When Maddie started this company, it was her creative vision. But once I saw it take off, I knew we could test it out on a college campus and rally support,” Katie shares.
Dartmouth’s unique culture and alumni network offered the perfect testing ground for the pajamas, featuring designs inspired by beloved Hanover and Upper Valley hot spots. Katie’s experience as a recent graduate added a personal touch. “Hanover is such a special place for students and alumni alike. The restaurants, the small-town feel—it's all part of the Dartmouth experience,” she says. This connection gave Katie confidence that the pajamas would be well-received.
A Community-Based Project: Connecting with Local Businesses and The Haven
Katie and Madelyn recognized that the Dartmouth community’s strong sense of connection could be key to their success. “Dartmouth is more than just a school; it’s a family,” Katie says. “People feel a deep emotional connection not only to the campus but to the town of Hanover itself.” That’s why they designed pajamas that featured iconic local restaurants, aiming to evoke a sense nostalgia to build a customer base.
The brand was also interested in giving back. They partnered with The Upper Valley Haven, a local nonprofit providing food and shelter, donating a portion of their proceeds. “I had previously volunteered with the Haven through the Dartmouth Women’s tennis team,” Katie says. “When we decided to donate a portion of our proceeds to them, it really resonated with the community.”
Local businesses were enthusiastic about being included. “I talked to all of the restaurant managers, and they were so excited about the idea. They loved the element of giving back,” says Katie. “Everyone knew about The Haven. It felt like the perfect partnership.” The collaboration strengthened the brand’s connection to the Dartmouth and Upper Valley communities.
The owners tapped into Dartmouth’s extensive network of alumni and current students to build a presence on campus. “Katie did an incredible job as a brand ambassador when she was a student, and now we have Olivia, who’s still at Dartmouth and helping manage the process on campus,” Madelyn says.
Olivia Galiatos ’26, a field hockey team captain, used her campus connections to spread the word. “When alumni see current students wearing or supporting something they love, it strengthens their bond to Dartmouth,” she says.
This approach—combining nostalgia, the business community, and philanthropy—became a cornerstone of their brand’s success, connecting generations of Dartmouth students, alumni, and local businesses in a meaningful way.
Overcoming Challenges and Early Successes
Launching a business can come with hurdles, and the early stages for Sleepy Saturday were no exception. One of the biggest challenges was finding the right manufacturer. “The first manufacturer we worked with was a complete disaster,” Madelyn recalls. “We ordered cotton samples and spent around $3,000 on them, but when I washed them, they all faded. I was disappointed because they were so expensive to produce.”
Despite this setback, Madelyn’s determination pushed her to keep going. “I started talking to other entrepreneurs like Matt Bartini of Mayor Clothing and Olivia Cleary of The Clearly Collective, getting recommendations, and finally found a manufacturer that worked.” She emphasizes the importance of persistence. “You have to be willing to shoot your shot, even when things don’t go as planned.”
Their persistence paid off when they secured a spot at a high end boutique in SoHo. “Honestly, I don’t even know how we got in,” Madelyn admits. “I think the owner was willing to take a chance on new brands.” This opportunity was pivotal, providing exposure beyond Hanover.
Their breakthrough came when an influencer with 200,000 followers purchased a pair and posted about them. “It was a total stroke of luck,” Madelyn says. “They went viral. Suddenly, the boutique was sold out, and we started getting more orders than we could have imagined.”
This success also presented challenges. “We quickly learned that having a viral moment is great, but it doesn’t automatically translate to sustainable growth,” Madelyn says. “The lead time for new inventory was two months, and without a big marketing budget, we couldn’t recreate the buzz.” The experience taught them valuable lessons about managing inventory and capital as a small business.
Madelyn negotiated with manufacturers to pay half in advance and the rest upon receipt. She also worked with retail partners to secure pre-orders. “I was upfront with them,” she says. “I told them, ‘Look, we’re a small brand, and we need half of the order paid up front to make this work.’ It wasn’t easy, but it was necessary.”
Expansion and Future Plans
Success has been sweet: Sleepy Saturday recently hit $100k in revenue for their first year in business--with their goal being to double that in their second year. With their initial success, Madelyn and Katie began thinking about how to expand beyond Dartmouth. “We knew that if we could succeed in a small, tight-knit place like Hanover, we could definitely bring this concept elsewhere,” Katie says. They explored high-end resorts as new markets. “We’ve seen great demand from high-end resorts and vacation destinations,” Madelyn says. “This year, we partnered with Deer Valley, locations in Hawaii, and a western ranch.”
While their retail success remains important, the brand is also committed to the wholesale model. “It allows us to predict inventory and demand,” Madelyn shares. “We prefer to build partnerships with retailers who know their customer base.” They also aimed for larger retailers, like J.Crew. “We designed a line specifically for J.Crew and even sent a sample directly to their headquarters,” Madelyn shared. Though they were met with a polite rejection, she saw it as part of the journey. “You have to be prepared for nine out of ten shots to miss, but you keep trying. That’s how you grow.”
They also considered diversifying their product line. Katie saw potential in athletic apparel. “We think there’s space in the market for athletic wear that’s both functional and a bit more fashionable,” she says. However, they remain cautious. “We’ve learned to stick with what we know works—like pajamas,” Madelyn notes. “But we’re excited to test out new ideas, particularly with high-end resorts.”
The Role of the Dartmouth Network
A crucial component of their growth has been the support from the Dartmouth community and business network. “Dartmouth has a unique culture of support, especially for alumni ventures,” Katie says. “There’s this sense that when one of us succeeds, we all do, and people genuinely want to help.”
Katie reached out to fellow athletes, sororities, and faculty to spread the word. “I knew that if I could get my teammates and friends on board, it would have a ripple effect,” she explains. “We got featured in The Dartmouth student newspaper, which really helped us get traction.” Faculty support, including a purchase and post from President Beilock, was also an ingredient in a recipe for success on campus.
Katie’s former tennis coach, Bob Dallis, was another key figure who encouraged her throughout the process. “Coach Bob always emphasized that life is bigger than the tennis court,” Katie says. “He encouraged us to explore our passions outside of sports and has been a huge support in this journey.”
Olivia’s role as campus representative was vital in engaging both students and alumni. “Being on campus has allowed me to connect directly with students, but also to help alums feel a part of the Dartmouth experience again,” Olivia says.
“The alumni network is incredible,” Katie says. “We’ve received mentorship, advice, and business leads just from having conversations with people who care about seeing fellow Dartmouth grads succeed.” This strong sense of community has been a foundation for their brand’s growth.
Looking ahead, the team remains excited about expanding their product line and entering new markets. “If there’s one thing we’ve learned, it’s that you have to take your shot, even if you miss most of the time,” Madelyn says. “The key is to keep trying, keep learning, and most importantly, keep believing in what you’re building.”
To learn more about Sleepy Saturday and to purchase from their latest Hanover collection pre-order, visit their website.