What is
Chicago Love?
Chicago Love is a lifestyle brand built on pride, purpose, and the unmatched spirit of our city. We create high-quality apparel and products that represent the culture, neighborhoods, and people that make Chicago one of a kind.
Our
Communtiy
We are a family of proud Chicagoans and supporters from all walks of life who believe in lifting each other up and showing love to the city we call home. We rep every neighborhood, every block, and every story that makes Chicago, Chicago.
Our
Mission
Our mission is to spread Chicago pride and positivity while giving back to the community that supports us. We’re committed to building a stronger, better Chicago through purpose-driven partnerships, local support, and creating opportunities that matter.
Our Products
Bracelets
T-Shirts
V-Necks: Circles
V-Necks: Rainbow
Our Founder
Ryan Lessam never picked up paint or a paintbrush until moving to Chicago and living in Wicker Park. Today, he is a self-taught abstract painter whose work is driven by raw expression, lived experience, and an unwavering connection to the city that shaped him. Without any formal training, Ryan developed his style through instinct, experimentation, and a deep appreciation for the energy and character of Chicago—a city that not only inspired his art, but ultimately gave him his path as an artist.
Want to join the team?
Contact ryan@ryanlessamart.com