We caught up with the brilliant and insightful Kelly Oakes a few weeks ago and have shared our conversation below.
Kelly, thanks for taking the time to share your stories with us today What’s been the most meaningful project you’ve worked on?
It has always been important to me to use my art to give back to the community in some way. I was living in Charlottesville, VA in 2017 and really thinking about how to do this. Then the riots happened in August, right across the street from my studio. It changed my little town in a horrible way. That is when I decided to do a series of portraits titled:
To See and Be Seen, To Know and Be Known: Charlottesville
After the August 2017 riots of hate and violence in Charlottesville, I felt called to reach out to the people that hung out at the homeless day shelter across the street from my studio. This was “ground zero” where the riots happened. I knew their faces as I saw them everyday, but wanted to get to know them, to know their stories. Painting them I quickly found that they were strong, proud people who had a (usually) happy life of family, a job, and a home which changed in a blink of an eye. I then started meeting and painting others who were not homeless, but had shown true resilience in their lives, refugees whose lives were forever changed by fleeing violence or persecution.
I was honored that I was able to spend time with these wonderful people, and I call a few of them my good friends now. Many of them did not even have a photo of themselves as they lived on the streets, so they were thrilled when I gave them a copy of their portrait.
I showed these 12 portraits in a Charlottesville Gallery in Jan 2018.
I then moved to Hillsborough, NC in 2018. I received a grant to do 12 more paintings:
To See and Be Seen, To Know and Be Known: Portraits of People Who Have Experienced Homelessness
This show includes twelve large portraits I have painted of residents of Orange County. They have found permanent housing in partnership with service providers and the Orange County Partnership to End Homelessness after time in shelters and/or on the streets.
I have always been drawn to paint the inner spirit of a person, to those who may be unseen in our community. I felt called to paint residents in my town of Hillsborough, and Chapel Hill/Carrborro who may feel invisible — whose struggles might be misunderstood, and whose inner strengths often go unrecognized.
I offered individuals the opportunity to be painted, compensating them for their time. I hoped the invitation to paint their portraits would give them the opportunity to tell their stories, to be heard and seen, and to then to see themselves mirrored back in the paintings.
My intention through these portraits, is to share the spirit of resilience in these residents of Orange County, some who endure day-to-day lives of real hardship, sometimes trauma, in order to bring to light the essential, inner story of someone who might otherwise remain unseen and unknown — in fact, to remind all of us to look beyond the facades, and see the person within.
All 24 paintings were shown in September, 2022 in a solo show at The Eno Mill Gallery in Hillsborough, NC.



Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I went to MD Institute College of Art, studying Graphic Design and Illustration. I worked in advertising for about 10 years until I had my first child. The “go-g0” schedule was not conducive to raising a family. I painted murals and decorative furniture while raising 3 children for about 18 years. One of my children has Aspergers’, so I worked hard to help him become independent. I started teaching art at a high school where my daughter attended and while doing that, started attending figure drawing and painting groups. A few years back, I took my summer off as teachers can, and attended the Art Students League in NYC. There I concentrated on painting portraits and figures. It was one of the most exhilarating times in my life!
When I returned home, I realized I had been living 1/2 a life. My soul only yearned to paint. I have painted every day since then, as well as teaching adults my passion to paint portraits.
I am most proud of my project combing this with helping the community understand people who are somewhat invisible in our town. Painting a series of people who are or have been homeless has been an honor and a privilege.



Is there mission driving your creative journey?
My goal is to use my passion to create for the betterment of others. I struggle with the typical problems of any artist: resistance, the voice of doubt, and to ignore those and take the risk to create anyway.
I find it much more satisfying to paint the portraits of people who are otherwise ignored or misunderstood. It fills my soul to have this reason/opportunity to get to know them. It may sound trite or corny, but it is absolutely true.
These pieces have not sold, but I have made copies of them to give to the individuals. I am keeping the show together to display them in other galleries to spread the idea that this world needs to stop and get to know others that may be overlooked.


What’s the most rewarding aspect of being a creative in your experience?
As stated above, it used to be important to me to sell my work. I now have a thriving commission business painting portraits of children and pets. I enjoy that and it helps pay the rent. But now that gives me some breathing room to paint what is important to me without the worry of selling them. So, I believe that artists can do both: paint (create) for yourself and for others.
Contact Info:
- Website: www. KellyOakesArt.com
- Instagram: @kellyoakesart
- Facebook: @kellydoyleoakes
Image Credits
Scott Smith, Photographer

