One on One with Jilleen Liao, Freelance Footwear Designer and Former WIFI Grant Recipient

Jilleen Liao is a freelance footwear designer and consultant based in Brooklyn, NY. A more than 15-year industry veteran, she describes her educational journey as “off the beaten path.” 

Instead of following a conventional college route, she immersed herself in specialized footwear programs, shoe-making classes, and apprenticeships within factories, gaining practical knowledge directly from the industry. With this foundation, she launched her own shoe brand, Onto, which she oversaw until she closed it in 2020. Jilleen currently works as a freelance footwear designer through her consulting company, Outside Dreamers. Her designs span skate, athleticwear, women’s comfort, fashion and more. 

She recently spoke with Two Ten about her unconventional journey to becoming a designer and shared the key lessons she carried forward from each stage of her career. 

How did you realize you wanted to work in footwear?  

Growing up skateboarding, I was very aware of function and utility as well as style within footwear. I got into design through an internship in New York City around 2007 and it wasn't until I met one of the women who was prototyping footwear at this internship that I realized that you could even do footwear specifically. 

What other experiences helped you grow your knowledge of footwear design? 

One of my first classes after that internship was with Emily Putterman at the Jewish Community Center. From there, I did a summer intensive at Cordwainers and then ended up working in some local factories for experience instead of going that traditional route of schooling. I apprenticed at E. Vogel's and also ended up getting a job as a senior footwear designer at Gentle Souls, which is part of Kenneth Cole.  

The man running Gentle Souls at the time, Wayne Finkelstein, was an OG “shoe dog.” He used to have his own factory in the Bronx as well. He saw a pair of shoes that I had made and was super impressed and basically took me on. I learned so much from that experience and we were able to create a great line together and collections for several seasons. 

After leaving Gentle Souls, I ended up feeling like I had been able to go through this comprehensive trial by fire experience of a very corporate, collection-oriented factory-to-sales-room pipeline. I also had a sense of confidence that I could do anything. 

Earlier this year, you received a WIFI grant to attend the “Professional Development on Performance Footwear” workshop, hosted by Arsutoria School in partnership with the University of Oregon’s Sports Product Management program. How was this helpful to your career? 

I was hoping to gain a deeper and updated understanding of current performance footwear technology. Higher performance shoes with micro-injection tooling often require different machines and technical knowledge that building a basic skate shoe doesn't necessarily have.  

The course encouraged me to think about what's possible when old-world shoe techniques and insights blend with new advances in tooling. I don't think I would have had the opportunity or space to sit and wonder about what is possible had it not been for that program. Also meeting amazing new people through that experience was great as well. 

How do you fill your time outside of footwear? 

I skate. Not the way I used to, but I still push around, which is super invigorating. Cruising down the street, wind in your hair — there's nothing like it. 

I've also gone birdwatching throughout this last year, which really teaches me to be present. With footwear, you're always troubleshooting and problem solving. Birdwatching, for me, has been really rewarding in terms of figuring out that internal alignment, listening and being in the moment. The more present you are for yourself, I think the more present you're able to be for other people. 

What advice do you have for women looking to enter the footwear industry? 

 Don't let uncertainty be a challenge. Remember the things that excite you.