Hailey Losselyong: Woman Painting Women

Hailey, holding a bag she designed.

Hailey, holding a bag she designed.


Hailey Losselyong grew up playing sports. Everything about her life pointed towards her playing collegiate soccer, until she suffered an injury that changed everything. 

At 13, Hailey broke her leg and returned to the sport after a short six months of rehab. The time away wasn’t anywhere near long enough to allow for a full recovery and with an often aching leg she continued to play in high school. Her injury, however, didn’t allow her to continue past that point. She enrolled in college on an academic scholarship and plans to pursue a business degree. Her future once again shifted with a single Adobe Illustrator workshop. 

“College was a wakeup call. I realized I had no interest in anything that anybody was talking about, because I was in the wrong program. And then I took one Illustrator workshop, and I was like this is it.”

Hailey, today, is an artist. It took her years to gain the confidence to identify as such, and years before that to find the courage to pursue painting as a serious career path. In addition to providing her with technical tools, the illustrator workshop helped kickstart a self-discovery and, in the timeline of events, acts as a clear change of direction.  

Instagram: @hai_ey

Instagram: @hai_ey

“When I first started painting I was painting things for other people because I needed money. I could just look at a picture and paint it. When I developed my own style, I felt more confident identifying as an artist.”

Her art focuses on the faces of women. In a recent partnership between Gumbo Media and the Ace Hotel in Chicago, Hailey led a workshop guiding participants through the face of Michelle Obama. During the Poler Vortex that shook much of the United States this winter, she encouraged donations to a local nonprofit that opened its doors as a warming center by offering free digital portraits to anyone who donated. Though she is young, Hailey’s becoming, of sorts, is such: A talented painter who is aware of the world she creates in, with a willingness to share that is increasingly hard to find. 

As a woman painting women, Hailey knows what it means to be unfairly overlooked. The hard truth of life is that in many spaces, talent becomes insignificant. What matters is drive and a consciousness of self-worth, which she also possesses and wears proudly.  

“I have been in situations where there aren’t a lot of women in the room and the same few men get picked to do certain things. We’re here and we’re just as talented. But we just have to keep finding things that make sense, and find people that want you. I don’t want to work for people who consider me an afterthought.”

To support Hailey’s work, visit her website http://www.hml.design for upcoming workshops and unique product releases.


gosia circle.jpg

Gosia Labno is a photographer and writer based in Chicago. She holds a B.S. in Media and Cinema Studies and an M.A. in Middle Eastern Studies. She is working on a collection of short stories chronicling the lives of undocumented immigrants in the United States. Follow.