Meet Caroline Leary

We’re excited to introduce you to the always interesting and insightful Caroline Leary. We hope you’ll enjoy our conversation with Caroline below.

Caroline, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

I developed my confidence and self-esteem through a journey of transformation and self-discovery that challenged me both personally and professionally. Early in my career, I faced a significant turning point. In medical sales, despite being successful and driven, I found myself struggling with depression and the overwhelming demands of being a new mother. I hit what I now call a “glass ceiling” that made me question my identity and purpose. For six months, I felt lost—uncertain about who I was and what I truly wanted from life.

Leaving a stable, well-paying career was not an easy decision, but it was a necessary step toward embracing a path that aligned with my true self. As I worked through that difficult period, I learned that the conventional definitions of success did not have to define me. Returning to school as a 40-year-old, in a room full of much younger peers, was both daunting and liberating. That experience forced me to dig deep and redefine my identity, ultimately rekindling a sense of strength, independence, and pride that I hadn’t felt in years.

This transformative period, which I sometimes refer to as my “little midlife crisis,” taught me that every setback is an opportunity for growth. Embracing failure as part of my journey, rather than a permanent state, has allowed me to develop a resilient self-esteem and a passion for pursuing what truly resonates with me. Today, I see each challenge as a stepping stone that has not only shaped my career in couture fashion but also enriched my personal life, empowering me to lead with authenticity and confidence

Thanks, so before we move on maybe you can share a bit more about yourself?

Caroline Leary is a brand with nearly four decades of inspiration, rooted in my lifelong passion for sewing and design. Sewing has been a constant in my life—from helping my mother create costumes as a child to designing my formal dresses as a young woman and even selling party dresses in high school. Growing up on a South Carolina farm instilled a deep appreciation for style and the importance of presentation, which grew stronger as I ventured from South Carolina to New York to Philadelphia.

A ten-year career in medical device sales taught me precision and discipline, yet I eventually encountered a glass ceiling that pushed me to reexamine my true calling. At a pivotal moment—when I was balancing the challenges of being a new mom with a sense of unfulfillment—I transformed a part of my home into a sewing studio. That space became a sanctuary where I rediscovered my passion for design and creativity, leading me to pursue graduate studies in fashion design at Drexel University.

Returning to school at 40, surrounded by a younger generation, was both challenging and exhilarating. It crystallized my vision for a couture line reflecting contemporary women’s multifaceted nature. This journey—marked by bold decisions, creative experimentation, and an unwavering commitment to my craft—has allowed me to embrace failure and success alike. Each step reinforced my belief in who I am, empowering me to design formalwear that not only makes a statement but also makes the wearer feel empowered, elegant, and confident.

What excites me most about my work is the opportunity to create custom pieces that emphasize the beauty and strength of modern women. My designs draw inspiration from the timeless elegance of the 1950s Balenciaga aesthetic, reimagined with a contemporary twist to suit today’s multifaceted lifestyle. While I currently offer personalized appointments to craft one-of-a-kind garments, my vision is also inspired by a future atelier concept—a dream of creating an inspiring space in Center City, Philadelphia, where art meets bespoke craftsmanship.

At Caroline Leary Studios, every custom piece is thoughtfully designed to make you feel graceful, empowered, and uniquely you. I look forward to continuing this journey, one exquisite creation at a time.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

Determination, empathy, and kindness are the three most important qualities I embody. I may not have always been the top student in every classroom, but I have never accepted anything less than excellence. Since childhood, once I set my mind to a goal, nothing could stop me from achieving it—a drive that has consistently propelled me forward.

Empathy is a quality that many overlook today, yet I believe it is essential not only for being a good person but also for personal growth. By viewing situations from others’ perspectives, we can enhance our own ideas and craftsmanship. Embracing diverse viewpoints enriches our work, infusing it with the creativity born from different cultures, experiences, and challenges.

Finally, kindness stands as the most vital of all. I firmly believe that confidence, fueled by kindness, can take you further than raw intelligence. When you have the courage to ask for a chance and the humility to offer help in return, you create opportunities for mutual growth. In my experience, people are generally eager to support and invest in others—if you give them that opportunity.

One of our goals is to help like-minded folks with similar goals connect and so before we go we want to ask if you are looking to partner or collab with others – and if so, what would make the ideal collaborator or partner?

I’m always interested in partnering and collaborating with creative, forward-thinking individuals who share a passion for elevating women’s style and self-expression. I’m looking for fashion designers, stylists, artisans, and creatives in the art and design space who appreciate the craft of couture and the importance of storytelling through fashion. If you’re someone who values innovation, attention to detail, and empowering women through unique, custom pieces, I’d love to connect.

Please feel free to reach out via my website or social media channels to explore potential collaborations. Whether you’re interested in co-design projects, events, or bespoke creations, let’s work together to bring inspiring, artful designs to life.

Contact Info:

Image Credits

Red and gold Gown:
Image: Nick Starichenko, UniPix
Model: Liliya Chiang
Event: FCIFF, Preview for the Spring Gala

Navy Pants and top:
Image: Shih Digital
Model: Aubrey Conley
Event: Philadelphia Fashion Week

Red and White Jacket/ Pants Set
Model: Monica Hill

Black and White gownn:
Image: D Rhodes Photos
Model: Makenzie DiVito
Event: Philadelphia Fashion Week SS 24

Navy column Gown:
Image: Maria V. Mont
Model: Maddy Ruff
Event: Philadelphia Fashion Week

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