Alright – so today we’ve got the honor of introducing you to Hannah Gerrity. We think you’ll enjoy our conversation, we’ve shared it below.

Hannah, thanks for joining us, excited to have you contributing your stories and insights. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

The story that comes to mind when I think of taking risks has to do with my first job out of college. I was newly married and living downtown Chicago. My music degree wasn’t earning me any money yet, so I decided to find a retail job to help make ends meet. I walked into my favorite brand and asked if they were hiring. I returned a week later to join a group interview, and thankfully, I was told to return for one more one-to-one interview with the store manager. She asked me to style some outfits, and then followed up with a slew of fashion questions that I had no idea how to answer. I remember very clearly how disappointed she sounded as she expressed her doubt that I was actually interested in this job at all. That statement lit something in me. I looked her in the eye, my voice shaking a little from the adrenaline I felt pulsing, and gave a fiery speech about how determined I was to work hard, how I was a quick learner, and how I genuinely loved the brand and its mission. After that speech, she told me she saw the fire in my eyes and decided to hire me on the spot. It was this job that started me down the path to becoming a personal stylist!

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’ve always loved fashion, but my first love was actually historical fashion and costuming. There’s something about the way clothing tells a story and captures a moment in time that’s always fascinated me — and that perspective really shapes how I work as a stylist today. I don’t just see outfits, I see the story a woman is telling through what she wears.

That love for personal style came to life during my first retail job. I worked alongside these incredible women — many of them fashion designers on the side — and being in that environment lit a spark in me. I quickly saw that styling someone wasn’t just about putting pieces together; it was about helping them see themselves differently. I’ll never forget one woman who broke down in tears when she saw how beautiful she looked in a retirement party outfit I’d put together for her. That moment made me realize this work has the power to shift how a woman feels about herself — and I knew I wanted to spend my life creating those moments.

That experience stuck with me, especially as I became a working mom myself. I deeply understand how easy it is for personal style to fall to the back burner. Between running a business, caring for a family, dealing with body changes, and the constant mental fatigue of managing so many roles, style can feel like one more thing to juggle. But I’ve also learned firsthand how powerful it is to show up as a whole person, not just as a mom or business owner. When I feel good in what I’m wearing, it re-energizes me, boosts my creativity, and makes me a better participant in every part of my life.

After years of working for two major styling companies at the forefront of virtual styling — and having styled thousands of women through those platforms — I realized what was missing was the heart. While those experiences gave me incredible expertise working with a wide range of body types, budgets, and lifestyles, I craved more one-to-one connection. I wanted to bring back the personal, compassionate, and deeply intentional experience of styling that truly centers each woman as a unique individual.

What makes my approach different is that I see personal style as a form of storytelling and an everyday creative practice. I don’t just curate pretty outfits — I help women rediscover their identity and unlock their creativity through what they wear. My mission is to help women — especially working moms — feel re-energized, confident, and bold enough to take up space in every area of their life. I want them to feel sexy on date nights, polished and powerful at work, and elevated even on the sidelines of a soccer game or at a park playdate. Because when we tap into our creativity and make intentional style choices, it positively impacts our mindset, our confidence, and how we show up in the world.

Can you tell us about a time you’ve had to pivot?

The pivot from being a stay-at-home mom to becoming a working mom was one of the scariest and most transformative moments of my life. I was at home with my baby, fully immersed in motherhood, but we needed more financial stability. I didn’t want to leave my baby, but I also wanted to contribute. That’s when I found the opportunity to work as a virtual stylist at Stitch Fix, just as they were starting to take off. It felt like a leap into the unknown, but it was the pivot that ultimately changed everything.

Looking back, I realize that pivoting — both in life and in my career — has often felt terrifying in the moment. But more often than not, it opens doors to new ideas and opportunities we weren’t even aware of. At Stitch Fix, I had the chance to work with tens of thousands of women across the country, not only refining my styling abilities, but learning how to adapt and embrace change in real time.

Becoming a working mom didn’t just bring more financial stability; it also opened up a future I hadn’t planned on. It allowed me to be present with my family while building a career I was passionate about. That pivot, though uncertain at the time, laid the foundation for my business today. It taught me that pivoting, whether in life or in style, can feel scary, but it almost always leads to new, unexpected possibilities. And that’s something I try to share with my clients — that embracing change in how we dress and how we live can unlock more freedom and creativity than we ever imagined.

Any advice for growing your clientele? What’s been most effective for you?

The best way I grow my clientele is through word-of-mouth, and that’s because I believe in giving each client an incredible experience from start to finish. It’s not just about the final result — it’s about how I show up for my clients every step of the way. When I help a client curate a beautiful wardrobe and they walk away feeling amazing, I know that’s going to generate compliments and attention. But what truly builds long-lasting relationships and brings in new clients is how I make them feel throughout the process.

I make it a priority to ensure that my clients feel heard, safe, and understood. When they feel like they’re in a judgment-free space where their needs and preferences are respected, they trust me not only to style them but also to share my services with their friends and family. Creating that level of trust and connection has been key to my business growth. I want my clients to feel like they’re not just getting a new look, but an experience that changes how they see themselves.

In the end, the best way to grow my business is to focus on creating those personal connections. When clients feel truly valued and cared for, they naturally want to pass that gift on to the people in their lives. That’s the power of word-of-mouth — it’s built on trust, connection, and the shared experience of transformation.

Contact Info:

• Website: https://Hannahgstylist.com
• Instagram: @hannahg_stylist
• Linkedin: https://www.linkedin.com/in/hannah-gerrity-2246b331/

Image Credits

Koury Angelo