Women We Love: Chicago Designer, Cynthia Ashby

October 7, 2019

Lux & Concord

The Chicago food scene has been getting a lot of press lately, but we can’t forget about the Windy City fashion scene! Local designers and purveyors are churning out amazing work that’s unique to our city, and if shopping local has become a priority for you, it really should also include fashion. Designer Cynthia Ashby has been working in the Chicago fashion scene since she started her own line while she was still in college. Yes, not even graduated, and the lady was already hustling! We love that 🙂 She’s giving us a peak behind her line, her inspiration and her city…


How did you come to start your own line?

It was created from the musings of my 20 year old self. I was taking a semester off of school and I was bored. I was visiting my parents and sitting in the room I used to sew in as a kid, literally wondering what I was going to do with my life. The idea came to me that I should start to create shirts and sell them. I was a scrappy art student and had developed a skill finding antique linens in the thrift shops of Chicago. These beautiful damask linens that had been preserved and pressed. I collaged together these fabrics, patched the worn parts, dyed them. I used every spec that could possibly be used. The garments I created were all different! I would cut and sew each one individually, not realizing at the time I was getting my education in design, pattern making and construction. This became my livelihood!

Thankfully, I was born with a fierce work ethic and was able to keep up with the demand from the local boutiques I would sell to. This was the mid 1990’s before everything we know now as “marketing.” Savvy shoppers in Chicago already loved searching out something unusual and local. They enthusiastically supported me! Angela Turley (recently closed Turley Road) in Andersonville and Kellie Poulos (her store is now called CouCou and Olive) in Evanston were some of my first customers. They brought me into their exceptional boutiques and that is where I met my niche.

I will always be grateful the those boutique owners in the early days who brought my designs into their stores and enabled me to start up and keep going. I started to expand selling to boutiques nationally in the late 1990’s. Being self taught, I went through a lot of ups and downs juggling my creative evolution with learning to be a business owner. Every step of the way having support from friends, family, employees, and my customers.

What is something no one tells you about being your own boss?

Perhaps that you are really not “your own boss.” I am always accountable to something or someone.


How do you craft your inspiration?

I am generally an inspired person. I have never really had to craft my inspiration – it is my inherent state. I simply do what I do! Designing clothing is very natural for me. With that said, there are so many aspects to designing something to market and produce. In my company, we put a lot of effort and resources into sourcing fabrics and dye techniques. Its up to me as the pattern maker to turn my ideas into garments that can be put into production successfully.


What is your typical day like now?

I spend my days designing and pattern making, working with my production team on developing product or problem solving, and general tasks and decision making in regards to driving the business forward. Some days I am bouncing around through all those things, and some days I am hunkered down working on a collection all day. As the business owner/designer I get pulled in a lot of directions.

How would you describe the Chicago fashion world?

The fashion industry in Chicago is very supportive. I have worked with manufacturers in Chicago for 20 years. They are honest and helpful!

What advice would you have for someone looking to get into the world of fashion?

If you thrive on change, love hard work, love to be challenged, go for it! Its a tough industry. It requires a lot of diverse skills – not just design, but manufacturing as well as a business sense. It will be a roller coaster ride-so love it! Cherish your moments of success, be flexible and learn from your mistakes.

What is the best advice YOU have received?

Learn to play by the rules. I’m still learning that!

What is your 5-year plan for the line?

I am planning to expand in a couple different directions. We are working on launching a line of uniforms as well as a menswear line. The uniform line will be marketed to artists and creative/boutique industries – companies that want a unique look for their staff. As far as the menswear goes, I have guys ask me constantly when I am going to make something for them. I dabbled in it here and there, but now I am ready to fully dive in. I can’t wait!