Meet Boots, the poet who leaves inspirational messages on Chicago’s sidewalks

After a 10-year relationship ended, she started writing poetry to heal a broken heart. Seven years later, she continues to write — but now she does so on the sidewalks of Chicago.

She goes by the name of “Boots.” It was the nickname her former boyfriend gave to her because of all the boots she owned, said Kimberly Brown. So she decided to use the nickname out of spite.

“We’re all damaged. It’s how we still love with a broken heart that matters” and “Invest love in the ones who stay” are two of the Pilsen resident’s most popular verses, which are spray-painted onto sidewalks, abandoned buildings and public spaces in cities across the country.

But she’s not still pining after her former lover, she said. Instead, she’s taken her art to 37 states and counting.

Brown, who is in her 30s, hopes to visit and spray paint her messages in all 50 by the time she turns 40 — an endeavor that can take some time as she awaits permission and invitations from cities.

In Chicago, her short poems about heartache, self-love and advice can be found stenciled in black or purple on sidewalks, there to perhaps brighten up the day for passersby walking with their heads down.

“I feel like we all need these positive messages just to remind us that we’re still human and we’re still trying and even if we have days we can’t get out of bed, there’s always hope,” she said.

But when does street art — some of which is unsanctioned — become graffiti? That line can be blurry, said Caitlin Bruce a communication professor from the University of Pittsburgh.

“Like any kind of public art, it seems like one of the core effects of this work is communicating a sense of intimacy,” Bruce said.

Graffiti “is not always meant to be understandable to a broader public, Bruce said. And in fact, a lot of the styles are meant to be kind of opaque or visually noisy. And so if we think about Wildstyle (graffiti), it’s hard to read. But if you’re part of that community, it’s very meaningful.”

Meanwhile, Brown’s art is meant to be accessible to everyone, the artist said. Even if her art may fade because of the wintertime salt on Chicago streets or in the sun on Texas sidewalks, Brown hopes the words she writes have a long-lasting impact on people who read them.

Brown said that sometimes her poems will get covered with graffiti, or artists will send her videos tagging over her writing.

She said that some graffiti artists also love reminding her: “There’s a difference between painting a huge wall and some stencils on the ground. And I 100% agree with them.”

Still, Brown is friends with some graffiti artists and muralists who have asked her to collaborate, though she hasn’t had the time to sit down and plan something that big, she said.

“I use spray paint as a medium to get the words across because the words are most important to me,” Brown said. “So, I try to focus as much as I can on just the words, even though it would be a great thing to do murals and stuff. It’s just not as much my focus right now.”

Brown was an eager reader of poetry from as young as 12, she said. She wrote poems as a hobby in her 20s, and counts poet Michael Faudet and New Zealand novelist Lang Leav among her favorite writers.

But her own writing career didn’t begin until after that fateful breakup. She collected 145 of her poems and compiled them into her first book, titled “Cancun.”

“There’s a chapter on self-pity and drinking too much and numbing yourself. I kind of explore all that,” she said. “So I think that’s why so many people related, because I didn’t sugarcoat it. I wrote about crying on the bathroom floor in the fetal position, drinking too much in hotel rooms — all these things. I wanted it to be as raw and real as possible.”

She also self-published a book called “Fury” in 2017, a collection of 245 poems accompanied by Polaroid pictures of abandoned places.

Her messages began garnering even more popularity in 2018 when she started putting stickers on street lamps and abandoned places with more frequency around Los Angeles, where she lived at the time.

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It prompted a change in focus from just writing to sharing her words through street art. The messages she spray paints with stencils, she said, are hand-picked and often different from the poems she shares online with her 143,000 Instagram followers and in her books.

In 2021, Brown moved back to Chicago. She grew up in the south suburbs.

“When I get a response from Chicago, it means more to me than any other city, because I’m from here and this is where I grew up,” she said. “So whenever I get tags from other cities, it’s exciting. But every time there’s one from Chicago, I get extra excited. It’s just hometown pride — I feel like my city supports me and that’s beautiful to me.”

Brown has also visited numerous other U.S. cities — in some cases, mayors have even invited her — to spray paint her inspirational messages on sidewalks and lampposts, including Corpus Christi, Dallas and Houston in Texas, Louisville in Kentucky, Memphis and Nashville in Tennessee and Indianapolis.

Although she has a day job, and also runs an Etsy shop where she sells her books and clothing, her art is her passion.

“I love what I do. I get to travel all the time and put up these incredible messages everywhere,” Brown said. “And it’s just super exciting and super fun, and the response I get from all the people — it’s absolutely incredible. I never thought that when I started this, it would turn into what it has and I’m so humbled and grateful.”

adperez@chicagotribune.com