What is City Self-Portrait?

City Self-Portrait is a community engagement collaborative art project started by Jessica Mailhot in May 2017 in Milwaukee, WI.

How it works:

Throughout the summer, Jess will be painting scenes of the city plein-air-style out in the street in different locations throughout downtown Milwaukee. A sign on her easel invites all passersby to take the brush and add a stroke or two and then sign their initials to the back of the canvas as contributing artists.

“These paintings aren’t just a snapshot of what was there but who was there. A city is not just buildings, it’s people.”

About once a week Jess will choose a new location to paint– somewhere with decent foot traffic, enough space to set up and an inspiring subject. She paints start to finish on site, which takes about 3 to 4 hours. All paintings will be compiled as a series and titled by the number of contributors for that painting.

All paintings and stories from this project will be posted here so check back regularly!

“Can I really? Are you sure?”:

EVERYONE is welcome: young or old, resident or visitor, even if you’ve never held a paintbrush before. The goal here isn’t perfection; this project aims to remind people they have something unique to contribute, to feel a sense of pride for their city, that opportunities to try something new are everywhere, and that going for a walk can be more than just getting from point A to point B.

So yes, I am sure.


If you are interested in being a host gallery for the completed series this Fall or in purchasing a print or original, please contact me here.

Questions, comments, recommendations are all welcome, too.

Interested in piloting your own City Self-Portrait project? Let’s chat!