OLIVIA CLEARY OF THE CLEARLY COLLECTIVE
"The most rewarding part is that no two stories are the same, and I feel like there is a power in this visual language, right? And that's a unifying factor between when I talk to someone at SpaceX and then I talk to someone who does the PGA—it's totally different but like everyone has this story to tell. The most rewarding part is that I get to learn about all of these stories and then bring it into this beautiful design that they appreciate." - Olivia Cleary
Olivia Cleary a luxury designer and entrepreneur, known for blending artistry and storytelling into high-end, custom products. She is the founder of The Clearly Collective, a design agency specializing in bespoke silk scarves and other luxury goods that capture the essence of destinations, colleges, and brands.
A graduate of the University of Virginia’s School of Architecture Class of 2020, Olivia later honed her business acumen through the Darden School of Business incubator program in 2024/2025. Her expertise in design, paired with a deep appreciation for craftsmanship, has led her to collaborate with prestigious brands, including The Ritz-Carlton, McLaren Automotive, L'Oreal, Four Seasons, Richemont Group, The NFL, PGA, The Olympics and top Platinum Club of America various private social clubs.
Through The Clearly Collective, Olivia creates meaningful, beautifully crafted products for both direct-to-consumer and B2B clients, including company offsites, donor gifts, and brand activations. She has been featured in CNBC and Garden & Gun, highlighting her ability to merge luxury with emotional connection, crafting pieces that evoke nostalgia, pride, and belonging.
Tell me about the initial vision behind The Clearly Collective and what spurred you to start it from Architecture School?
The vision for The Clearly Collective grew as I realized the potential of what I had. Initially, it started as a personal project, something I was excited about doing on my own. In architecture, you don’t have much agency or liberty to pursue your own creative ideas, especially when you're at the bottom of the totem pole. You're often stuck doing grunt work, like designing bathrooms. Having something on the side that I could control was fulfilling, and as it grew, so did my vision. I recognized a huge gap in the market when it came to storytelling. So many industries lack storytelling and the beautification of what is often a corporate experience. I thought we could bring this to everything. I started with collegiate collections because I had just graduated from college and knew this concept would resonate with consumers. Then, I expanded into destinations and brands. The vision has evolved as I’ve learned more about how different niches and communities can express themselves through storytelling.
Were you always entrepreneurial growing up, or was this a spontaneous vision you pursued to see where it would go?
Yes, but it wasn’t intentional entrepreneurship. I would do something that people found interesting, and then they would start offering to pay for it. That’s how my ventures grew into businesses. In high school, I started my first company, which involved around 500 students per year in Concord. We had a project called The Leaf Project, where every freshman had to collect, identify, and press 20 different leaves using their Latin names. I loved hiking and collecting leaves, so I always had extras. People found out, and I ended up running a leaf bartering business—selling leaves for the project. The Clearly Collective started in a similar way. My friends would say, This is really cool, I want to buy it, and I was surprised but went along with it.
What inspired you to start with scarves?
I experimented with different canvases—I tried pants, drew on mannequins, and created large-scale canvas work. But it was hard to produce those at scale. I wanted a way to print my designs repeatedly and distribute them, and that’s how I landed on scarves. They became another canvas for my art.
You go through many iterations before transforming your designs into final products. Can you walk us through your creative process?
My first prototype was a really bad polyester silk scarf. I bought it in a roll, cut it myself, and sewed the edges because I didn’t want to invest too much money upfront. Everything was on a pre-order basis—I told people what I was planning to make, explained the quality level to expect, and sewed the scarves myself for my friends. They were supportive and said, Sure, we’ll buy them. That early version was quite different from what we do today.
What has been the most rewarding part of connecting and bringing those stories to life?
The most rewarding part is that no two stories are the same. There is power in visual language, which acts as a unifying factor. I can talk to someone at SpaceX and someone at the PGA, and while their industries are completely different, they both have stories to tell. The most fulfilling part of my work is learning about these unique stories and transforming them into beautiful designs that people appreciate.
What have been the most significant challenges and turning points in developing The Clearly Collective?
One major turning point was when McLaren reached out to me. That was a validating moment in terms of my work’s quality. However, it didn’t mean financial stability—one-off projects aren’t enough to sustain a business. I realized that for the company to succeed, it needed recurring revenue. Another turning point was when I was offered a dream job as the number two at a luxury store design company. I was thrilled and told my prospective boss that I still wanted to work on The Clearly Collective on the side, but he said I couldn’t. That was when I realized that even though this would have been my dream job a year ago, I believed in what I was building, too much to set it aside. That was my confidence turning point. My financial turning point came after quitting that opportunity and joining the UVA incubator program, where I learned how to run a business properly. They taught me about cash flow, marketing, and scaling. I went all in and was finally able to generate sustainable monthly profits. One of my biggest struggles has been understanding the relationship between money and time. As the head of a company, I needed to learn to buy back my time. For a long time, I tried to do everything myself, resisting help because I wanted full ownership as an artist. But you can’t scale that way. A friend told me you need to spend money to make money, and I finally got it when I bought a $200 label printer. That simple investment saved me hours that I could have used for sales calls. Recognizing that strategic investments free up time was a game-changer.
What advice would you give to undergraduates looking to start a company?
Take calculated risks—very calculated. I am risk-averse. Some people can jump in headfirst, but my approach was to have a full-time job first. It gave me structure, taught me how corporate America works, and helped me understand company culture, work hours, and meeting structures. When building something new, sometimes your idea is ahead of its time, and people don’t get it. If they don’t understand it, the best way to introduce your concept is to marry it with something familiar. For example, my first scarf designs were random. They were beautiful, but they didn’t resonate with people. However, when I took my design style and applied it to college architecture, suddenly, it clicked, and the business grew. If I had only put out random art, it would have taken much longer to gain traction. Work with what people understand first—build credibility, and then you can start experimenting.
Are there any exciting developments you can share?
This holiday season has been incredible. We’ve hit record-high monthly revenues, which is exciting just six months in. While I haven’t signed anything yet, we are in the final stages of deals with golf clubs, wineries, castles, and amazing eco-hotels in treetops. We’re also launching a prep-school collection, which feels like a natural extension of our collegiate line. Once one school joins, the others will follow easily.
How do you see The Clearly Collective evolving to keep up with changes in the luxury market and consumer culture?
Trends will always change. I was lucky that I hit the scarf trend at the right time. But even when scarves fade, the core idea of storytelling through design will remain. The medium may change, but the essence of transforming communities into wearable and usable accessories will continue. For the next steps, we’re focusing on destinations this spring. Right now, we’re positioned as a luxury collegiate brand, but I want to elevate The Clearly Collective into an all-encompassing design fashion brand.
Quick Takes:
Female founder you look up to?
Sara BlakelyGoals for 2025?
I want to work with more European-based companies when I move there. Breaking into that market, which is rich in history, is something I’m excited about. I understand the U.S. market, but I’m eager to explore what’s possible in European and Middle Eastern architecture-inspired designs.