Self-Taught Artist Hailey Losselyong Manifests Confidence Into Her Work

From avid soccer player to established visual creator, Hailey Losselyong has brought her work to life by studying the duality of her subjects and focusing on exactly what her work has to say. Catch her at her next pop-up show on December 14th & follow her on socials!



Introduce yourself.

I’m Hailey Losselyong, 22 years old and a visual artist here in Chicago.

You describe your childhood as sports-based. Did you always have an interest in art despite that?

My mom and grandma are very crafty, DIY type of people. They’re not painters or anything like that but I definitely got the creative bug from them. I picked up a bunch of random hobbies throughout my childhood. I bounced around a lot and didn’t put too much time into drawing because I was playing soccer and other sports full time. I started drawing again when I went to college because I needed dorm decorations and I really enjoyed it. I had an interest in art when I was young but never actually imagined that i’d make it my career until three years ago when I decided to be a freelancer.

When you first started painting, you mostly did requests for other people. When did you start investing in your own work?

Many requests were portrait-based or faces and people would send in photos of themselves or loved ones, but I never did anything the way I do now. It was more realistic looking portraits and I got bored. I was broke in college so I just painted whatever they wanted me to paint, but after awhile I stopped taking those requests. I became uninspired and it wasn’t fun anymore. If you’re coming to me specifically, you should be coming to me for my work and style. I don’t even know how I found my style, it sort of appeared out of nowhere and I ran with it. It reminds me of makeup tutorials, how they block everything out on their face before they start blending everything.

Before you started freelancing, you attended DePaul for a bit. What did you learn on your own that you wouldn’t have been able to learn in a classroom?

Self-sufficiency. I took one art class in high school because I was forced to and one Illustrator class in college for six weeks but that was it. I’m very independent and I was trying to figure everything out by myself, which I don’t regret, but I’m also constantly learning from people. The whole classroom thing works for those who really need that structure to check off their bases but I’m not a very structured person. I go with the flow and would rather not do things that make no sense to me. In school, you learn about finessing your way through everything. Having to pay somebody and finesse them into giving me a grade that I don’t care about is a lot! How can teachers tell me my opinions are wrong? I was working to pay for college myself and it didn’t work for me. I didn’t get the point. I wouldn’t even want to go to art school in the traditional sense. I strongly believe in working in the field, even as an intern, because it’s better to get real work experience. I did an internship and it was great. I like physically being places and working, not just sitting and writing things down out of a book in a classroom.

What caused you to expand into fashion?

Before I started painting I was into fashion. I thrifted a lot for re-purposing which is what I do now in every aspect, re-purpose things. Thrift stores are the perfect place to do that because you don’t have the pressure of spending a lot of money. If you mess up, it’s fine. Combining art with fashion was never about selling it to people, it was about me wearing it and having different things for myself. Eventually other people just started wanting them. I’m still making things mostly for myself first. I’ll wear it a couple times and then somebody else can have it. It’s another way to have fun.

By writing “Leave Me Alone” on certain clothing pieces, how do you want them to be received by the public and those that wear them?

Part of me doesn’t care how it’s received because I know the people that have an issue with what’s being said don’t get it. The main purpose of Leave Me Alone is for calling out street harassment and people being bothersome in general. I did my first pair of pants over the summer a year ago and I wanted to write Leave Me Alone on them because I get bothered every time I go outside. It’s annoying. I put it real big on the front. First night I go out, I’m followed down the street into a 7/11 by a group of men, bothered and harassed within the five minutes I was alone waiting for a friend. I can literally write it in big letters on my leg and I’ll still get bothered. I started taking it up a few notches with huge bags and jackets. I made a big purse for a girl and she told me she wears it on her commute to work and nobody bothers her. All the girls give her great compliments and it’s because we all feel the same way. I want to be able to walk by myself! When things like that happen to you and you’re by yourself, it’s scary. It makes you feel gross or that you’re doing something wrong. Out in LA, I was cursed out by a man because I didn’t cross the street when he did. I was called a stupid fucking bitch in the middle of LA when no one else was around and I have to walk away and not say anything because I could be harmed. The city girl in me wants to come back and confront him but girls get killed for even saying anything. These clothes are a really important message that I’m not going to be nice about. There’s no “please” in front of it, just don’t talk to me.

What was the inspiration behind your first solo art show, Duality?

My thought for the first show was that I wanted to be in charge of everything. My boyfriend is a professional photographer and being around him has made me realize that I can do the whole process. I can take pictures of the women, choose the photos I really want, and then make it into a painting. I used all creative women in Chicago who are doing cool and different things in the city. The photos were black and white next to the colorful, bright paintings, re-imagining each piece and the two sides to it. For example, the one with Jean Deaux is very calm looking and serene yet her middle finger is up. You can be relaxed and cool while also being bold and bright. The show itself was a lot of work. I had a soft opening for people in the show and my family, which was less pressure. The following week I had it open to the public and I think it was well received. A lot of people came through that I didn’t know, which was great. It was an overall positive experience. I didn’t do it by myself but I do know that I can include more help next time. It’s necessary sometimes.

You recently began teaching painting workshops that give participants a chance to make their own art. How does it feel to be the instructor and have them look to you for guidance?

My part time job is sip n’ paint classes which helped in giving my tips and tricks. It was different teaching people something that I do personally, even though it’s more generic paintings. A lot of people do things differently than how I would which is what I was encouraging because I want to give them that base and let them go with what they’re feeling. Being a self-taught artist I don’t have that classroom structure so I don’t have all the answers in my notes, you know what I mean? I figured a lot of things out from that first teaching experience such as the things I know, but can’t say to other people. The color wheel and color theory, for example, I don’t know from actually learning it, I only know colors from studying them for my paintings. I’ve tried to identify all those technical things to help the everyday person learn those things too.

Let’s go through your tattoos as some of them are your original work. How do you decide which ones you want to get tattooed?

All of my tattoos are outlines and two of mine are my own designs. I don’t think too hard about my tattoos. The first one started as a sketch I was doing for a bag. I had never gotten anything of my own on me and I was in LA for work by myself and did it there. The artist got it down to a T and didn’t change anything. My other one was from my first show and I wanted it a little different. I gave the artist the photos and told her I wanted it to be blue and a china print pattern. She actually opened up a shop in Chicago with all female artists called Time Being Tattoo. I was keeping them hidden but as time goes on and I become more “successful” in my field as an artist, I don’t care as much. I’ve had a couple people who said they were going to get my work done on them but I’m still waiting for the first one! When somebody does I’ll be really excited.

In the “It’s About Time” project, your art revolved around inspirational women in society. How have you seen your work impact women and women of color?

Women love seeing the re-imagination of the portrait being in different colors and unusual looking. Women of color, in particular, aren’t highlighted as much as they should be, especially in art. I’ve had a lot of people be very excited to see themselves in artwork. The word itself has a sound to it that isn’t very attainable to everybody but it’s exciting to be able to highlight women that deserve recognition and want to feel beautiful. Being able to do that is very humbling.

Written by: Andrea Carrillo