Past Lives: Grayes founder Stephanie Ray


‘Past Lives’ is an ongoing column about the past careers of entrepreneurs and business leaders. The column recounts each person’s experience in various industries, from finance to sales, or simply, the nine-to-five grind. More than anything, ‘Past Lives’ is a story about how one person has reached their potential, and cut themselves loose from what was expected. 

Written by Amanda Scriver

Even though I went to law school in New York City, it may surprise you to know I’ve actually never practiced law. I studied finance at the NYU Stern School of Business, and I graduated in 2012. Then I began studying at Fordham University’s Law School. While there, I became focused on becoming a matrimonial lawyer—it was my dream. Hearing clients’ stories and helping them through divorce seemed like a really fulfilling job.

In 2014, I landed a summer internship at a matrimonial law firm. It would be three month’s long, so I spent a lot of time planning what I was going to wear every day. While I was out shopping, I realized there weren’t enough retailers that offered fashionable and affordable women’s workwear. I couldn’t find anything I loved or felt good in. Everything I found was strictly workwear; I could and never wear the pieces I bought with a pair of jeans or on a night out.

My brother, who was also preparing for his summer internship in the financial industry, didn’t have the same issue. He could rock a well-tailored suit during the day and wear the same thing to events in the evening. To me, this was disheartening. Why shouldn’t I love my nine-to-five wardrobe as much as I love my favourite pair of jeans?

I wondered if colleagues and friends were having the same wardrobe struggles as me, so I began asking around. Turns out, they too didn’t love their work clothes, and price point was a significant obstacle—everything that looked good was too expensive. That’s when the idea came to me: I wanted to create the perfect workwear line for women; a collection of pieces that women could love, even when they weren’t at the office.

I kept the idea at the back of my mind throughout law school, but only began to consider my own fashion line a viable business option when I graduated from law school in 2015. I decided to name it Grayes. It felt relevant to the women’s professional wear product category. But choosing the name was also personal—it’s a combination of my name and the names of my immediate family.

I knew that pursuing Grayes would be a huge risk, but it was also exciting—I believed in it and I wanted to make it happen, admittedly more than I wanted a career in matrimonial law. When I brought the idea up to my family, they were encouraging. In retrospect, I had no idea what I was getting myself into, but I absolutely love what I do! Every day is so exciting and challenging. It’s been so amazing to see people wearing clothes we designed and manufactured.

We started off with a pop-up at The Richmond in May of 2016. The goal was to get to know our customer. It was a great opportunity to hear feedback directly from our customers, and to better understand their needs. We learned what they were looking for in terms of style, price point and functionality. After the pop-up, we hosted smaller trunk shows so that we could continue the conversation with our customers. We knew that we needed a website to support these initiatives so we created something simplistic to start. After that, we took our findings and launched our e-commerce website in the fall of 2017.

It also turns out, my legal education has been beneficial to starting Grayes. One of the common threads between being an entrepreneur and a lawyer is having solid problem-solving skills. Training in law involves putting pieces together to solve big issues, and life as an entrepreneur consists of so many moving parts. You never know which ball will drop, and you can never anticipate the plethora of difficulties you might face. The only thing you can control is your ability to tackle problems, when they do spring up.

I had no fashion design experience, and that was one of the most significant challenges I had to overcome with Grayes. Early on, I made the decision to do the design and development in house and contract a local factory to manage production.  As a company, we had to start from scratch: I learned about everything from concept development to fabric selection to production. I booked meetings with everyone I knew in the industry so I could absorb as much as I could. Eventually, networking led me to find our current design team—they’ve helped bring Grayes to life.

My advice for anyone itching to start their own business is to stay strong and persevere. It’s not an easy path. You’ll encounter a lot of naysayers and obstacles along the way. It’s crucial to continue to believe in yourself and your idea. At the end of the day, it’s your vision, and it’s up to you to make it happen.