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Artist Sabrina Siegel’s Playful $10 Digital Portrait Series

The Chicago-based illustrator explains her quest to help people feel a little more seen and understood

Visits to galleries, art fairs and pop-ups used to serve as an introduction to new artists. Now, we are often left to our own devices—sometimes literally—as was the case when we stumbled upon Chicago-based artist Sabrina Siegel‘s Instagram page. A graphic designer and illustrator with experience in advertising and branding (and a degree in psychology), Siegel’s work touches on the intimate parts of everyday life and unseen emotions.

Considering her penchant for portraying the human face and all its quirks, Siegel recently had an idea: she opened up her Instagram inbox and posted an offer for $10 digital portraits. Based on a submitted photo (or photos) and social media images (we recommend giving her access), Siegel creates a portrait and sends it within days. The resulting playful, observant and fulfilling portraits are delightful, personalized artworks—and recipients see themselves through Siegel’s eyes. But, as Siegel explains in our interview here, she sees even more.

Your work balances realistic depiction and cartoon characterization—especially of people and situations found in everyday life. Did your art start as observations of your own life? 

Each piece stems from observations, conversations and personal life events. When I settle into a drawing, I reflect on my experiences, and gravitate to the ones that feel ridiculous, socially buried and/or relatable. When developing a style, it helps that I’m making work for myself. Because a lot of my work has been self-initiated, I have been able to choose the subject matter, and naturally reflect my personality, and viewpoint, into the visual style I build. Through this, I’ve been able to maintain a level of honesty, and shape both my tone and visual style as a unit.

There’s underlying humor in your art. It’s there at first glance and then secondary jokes and auxiliary commentary surface as you look around. Is the goal to be funny or transparent in your art?

My goal is to make art that initiates a pause and, hopefully, allows people to feel understood. I’m a pretty internal person, so I process a lot through drawing. I challenge myself to elicit a certain level of vulnerability in my artwork. I just want people to see my work and be able to relate to it, and to not really know what to feel. Plus, I get through things with humor and sarcasm, and I naturally project that into my artwork. Sometimes I feel like I’m riffing with myself; the longer I work on the piece, the more jokes I can attach to the situation, and then incorporate them into a piece.

How did you get into drawing people? Is it challenging to maintain your style when making portraits?

I admired Picasso’s work growing up. His abstract representation of people introduced me to this wild concept that art doesn’t have to look incredibly realistic, and inspired me to get into figure drawing in a looser way. That was the first spark. From then, its been pretty dynamic as I figure out what my artistic interpretation of people looks like. The challenging part isn’t necessarily maintaining my style when drawing people, but determining how they react to situations while clarifying a message.

Tell us about your $10 made-to-order portrait project. 

After my college graduation, I didn’t have a set plan. I spent the summer selling portraits just for some extra work. I have always enjoyed drawing people, so it just kinda clicked as an idea one day. Fast forward a couple years later, I found myself with some free time, but this time due to the current pandemic. It just kind of felt like everybody was a little rocked. I saw the world needed to lean on art, and that I could sell portraits for $10, keep them digital to support the idea of social distancing, and do my small part to spread some art and help people feel a little more seen. It’s eventually become a way for me to earn some money while I’m furloughed, but was initially an effort to share positivity and spark some excitement in a time of social isolation.

Do you see all of the portraits that you’ve made as characters in your universe now? It’s so fun to tap through them all.

It’s been a lot of fun to hear from people because I get to hear all the details that people want me to include in their portraits, or in ones for their loved ones. It’s just a wholesome experience to watch people pay attention to the traits they admire in themselves, and for them to speak on quirks that build their own identity. It’s also a helpful exercise for me to be able to consider different traits that I can add into my own artwork to lead to more people feeling seen.

Images courtesy of Sabrina Siegel


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