People and Places: Clearly Collective's Olivia Cleary on Starting with Structure and Creating a Brand

By Pat Dimond

Olivia Cleary is an architect-turned-entrepreneur who founded Clearly Collective, a gifting company specializing in bespoke designs inspired by communities, destinations, and brands. With clients like McLaren, Cartier, the US Olympics, and Ritz Carlton, she has organically grown her business through social media and word of mouth. After bootstrapping her company, Olivia fully committed to it in April 2024, joining UVA Darden's incubator program. She’s now preparing to move to Milan to launch her destination collection in spring 2025.

PD: I’ve admired how you scaled Clearly Collective. How did it all start?

OC: It really began as a personal project. I wanted to create meaningful gifts for friends, so I started painting in a style that reflects my architectural training. At first, it was on canvas, but I soon began experimenting with other materials. Early on, I bought a mannequin, spray-painted it, and applied my designs. Eventually, I moved on to clothing, like painting on white pants for friends. Another friend asked me to design pants that featured her favorite places in New York, and that’s when I realized I could personalize these items in ways that resonated deeply with people. From there, it grew into a business.

That’s such a unique concept, personalizing items based on a sense of place. I imagine people felt really connected to that. Did that play a role in how Clearly Collective scaled?

Absolutely. People are deeply connected to their sense of place—whether it’s a neighborhood, a college campus, or a childhood home. When I realized that architecture, particularly the iconic designs we all know and love, can evoke that kind of nostalgia, it made sense to use it in my designs. I started with scarves, using architecture from my college, UVA, and it took off. People loved having something that was a bit more elevated than a UVA sweatshirt or shirt – the scarves reflect a piece of people’s personal history.

What was your initial reaction when people started connecting with your designs in such a big way?

I was honestly surprised at first. What started as small, personal projects for my friends suddenly turned into something larger. When I first launched the scarves, I had a small gathering to show them off, and I sold about thirty scarves that night. It was more of a party than anything else, but it got me thinking about how I could make this more meaningful for a broader audience. The scarves were my first real product, and I remember cutting and sewing them myself. They weren’t perfect, but people loved them because they connected to the story behind the design. After that, I reinvested the profits into improving the product, and things just grew from there.

You quit your full-time job to focus on Clearly Collective. What was that transition like?

I had been balancing both for about two years. My bosses were incredibly supportive—they even encouraged me to enter art competitions. As things with Clearly started to get serious, I reduced my work week to four days. Eventually, my studio at the company dissolved due to restructuring, which felt like the right moment to make the leap and focus solely on Clearly. It was tough to leave because I had such strong relationships there, but the timing felt right. They were all so supportive of my decision, which made it easier.

I remember one colleague pulled me aside before I left and said, “I hope the next time I see you, it’s in Architectural Digest or somewhere just as big!” It was one of those moments where I felt a lot of encouragement to take the plunge.

“People and brands want to express pride in what they stand for.”

— Olivia Cleary

That support must have felt great during such a pivotal moment. I imagine it was still a big leap, though.

Absolutely. Leaving the security of a full-time job to pursue something like this felt daunting. But at the same time, the restructuring at my company felt like the universe giving me the nudge I needed. It was either stay and start fresh with a new team, or dive headfirst into Clearly Collective. I chose the latter, and I haven’t looked back.

You’ve worked with some big brands—McLaren, Bacardi, L'Oreal. What’s the secret to a successful brand collaboration?

It’s all about personalization. People and brands want to express pride in what they stand for, and I bring that to life through meaningful, bespoke designs. Whether it’s a person’s favorite city block or a brand’s iconic imagery, the collaboration works because it’s tailored and meaningful. I approach each project with the mindset of reflecting the brand’s values and community. Essentially, I’m collaborating as an artist, making sure every detail is intentional and resonates with the brand’s story.

When you’re working with those brands, do you find that it’s the same approach to personalization that resonated with your individual customers?

At the end of the day, whether it’s a large brand or an individual, people want to feel seen and understood. For example, with McLaren, they wanted to convey the essence of their brand—luxury, precision, speed. But at the same time, it had to feel personal to the people engaging with the design. So, it’s about taking what makes that brand unique and expressing it in a way that feels intimate, even if it’s for a larger audience.

In the past you’ve used social media as a tool to crowdsource ideas and inspiration for your designs, especially for the collegiate line. How does that work?

It’s been a game-changer. When I started designing for specific communities, like universities, I knew I needed to tap into what mattered most to the people there. Sure, I could research iconic buildings or symbols, but sometimes, the places that matter the most to people are the ones you wouldn’t expect. A small café, a particular gate on campus that has special meaning—those are the details that resonate with people on a deeper level. So, I crowdsource feedback from alumni, students, or people living in the area. It gives the designs more authenticity and makes them feel more personal.

How did you end up studying architecture at UVA?

It’s funny because I didn’t set out to be an architect at all. I’ve always been creative—drawing, painting, all of that. My parents wanted me to channel that creativity into something practical, and architecture seemed like a good fit. It was between that and industrial design. UVA had a design-thinking program that really appealed to me, so I ended up there. While I wasn’t one hundred percent sure about pursuing architecture as a career, it gave me the foundation to think creatively within a structured process, which has been invaluable in running The Clearly Collective.

How do you think your background in architecture has influenced your design approach with Clearly Collective?

It’s had a huge impact. Architecture is all about understanding space, structure, and the relationship between people and their environments. That’s exactly what I do with my designs. I’m creating wearable art that reflects people’s emotional connections to specific places. Whether it’s a scarf with a campus design or a pair of pants featuring someone’s favorite city block, it’s all about capturing that relationship between person and place. My architectural training taught me to think about how people experience the world around them, and I apply that to every design I create.

You mentioned scaling Clearly Collective. What are your goals for the next six months?

I’m really focused on expanding the brand in a few key areas. First, there’s the collegiate line. I want Clearly to be the go-to brand for celebrating life’s big moments—whether it’s graduating from college, returning to your alma mater, or even just cherishing a place that means a lot to you. Beyond that, I’m working on a destination line, focused on summer spots like the Amalfi Coast, which I’ve already started designing for. And, I’m moving to Milan, which I’m so excited about. It’s the heart of fashion and design, and I can’t wait to immerse myself in that culture. I’ll be traveling around Europe, drawing inspiration from different places and turning those experiences into new designs.

“Figure out what gives you energy and make time for that, even if it’s on the side at first.”

— Olivia Cleary

I can’t wait to see how your travels inspire your work. You mentioned luxury earlier—how do you define luxury?

For me, luxury is more about creating an emotional connection than attaching a price tag. It’s about beauty, comfort, and meaning—the things that make you feel special in a way that money alone can’t buy. True luxury evokes emotion, nostalgia, and a sense of connection. It’s not about how expensive something is, but how personal it feels and the story behind it. That’s what I strive for in my work—designs that capture a little piece of someone’s story, making them feel luxurious because of the meaning they carry.

That’s a nuanced way to think about luxury. Do you have any advice for people starting their careers, especially those pursuing creative or entrepreneurial paths? Would your advice be any different for women?

My biggest piece of advice is to start with structure. I don’t think jumping straight into entrepreneurship is for everyone, especially in the creative world. Working in a corporate environment first gave me the tools and structure I needed to later succeed on my own. I learned how to manage time, run meetings, and handle the business side of things. On the creative side, figure out what gives you energy and make time for that, even if it’s on the side at first. Build off what excites you and eventually marry that with something that resonates with others. If you’re doing something you don’t enjoy, you’ll burn out quickly. So, make sure your passion drives your work.

For women, or really anyone facing obstacles, my advice is to stay confident. People may not take you seriously right away, but if you believe in yourself and your work, that confidence will shine through. Don’t let anyone undervalue what you bring to the table.

What are you most excited about right now?

I’m excited to get out of the U.S. and experience new cultures in Europe. I think it’ll open up so many new ideas for my work and new lines that will come out of The Clearly Collection. I’m looking forward to discovering what people value in different places and how I can translate that into my designs. I think there’s so much potential to create meaningful, beautiful textiles that reflect the essence of different cultures and places.

Who are you admiring right now?

I have to say I've always admired Sarah Blakely of Spanx. From the way she built her company by herself to the way she's found balance. She does it incredibly well.