Jamie Chiarello: Portraits of Profound Humanity
Jamie Chiarello, oil on cardboard, 2025
November 2025This no-holds-barred artist explores the beauty of imperfection in her portraits, paintings – and handwritten signage – in Jackson Square.
– by Caroline Rowe
This column is underwritten in part by Karen Hinton & Howard Glaser
Artist Jamie Chiarello spends her days creating 15-minute portrait studies for a steady stream of passing tourists on Jackson Square, but her aspiration to celebrate the beauty of human error – in a world increasingly opting for artificial perfection – is anything but pedestrian.
Chiarello’s first visit to New Orleans was in 2003, where she filmed Mardi Gras filler footage for a videographer.
“He hired me to go around and interview people… we would be like, ‘do you think this is the peak of human evolution?’” That question would be received with a resounding “WOOO!”
Chiarello immediately observed the differences between the street art sales in New Orleans and New York City, where not having work in a gallery placed you lower on the totem pole than other working artists.
After relocating to the French Quarter, selling her work felt like being a small, but valuable part of an interconnected ecosystem. In Chiarello’s eyes, Jackson Square is a community. She casually refers to her fellow artists on the square as “coworkers.”
One experience she describes as formative began in the “cart yard” – a gated storage space next to Café du Monde, where Jackson Square artists store the carts they use to work from and store their art. used to move their artworks across the street.
“The interior of it looks a lot like [a set from a] horror movie,” she says, laughing. “It’s a terrifying kind of space, but getting a spot in there was tremendously difficult.”
Shortly after securing a space in the cart yard, she recounts how the wheels of her cart were stolen. She had saved up for new wheels to conduct business during the Superbowl, but when she brought the wheels to the cart yard for reattachment, she found the rest of the cart had been stolen.
At the time, Chiarello was devastated, but she found her coworkers empathetic and generous.
One artist was generous enough to loan Chiarello his cart for the season. Soon, another Jackson Square artist built Chiarello a new cart she could keep for good, a pink one that she says is non-binary. She named them Steve.
“This is a good example of what I experience as true community on the square,” she says.
“It reminded me of the way you would get a Rolex if you were a CEO and that’s your signifier. You put in your time. So I got my cart.”
Jamie Chiarello with her work on display at Jackson Square
There is no question as to whether Chiarello has “put in her time.” Since 2010, she has been hosting weekly life drawing groups, where artists gather around a nude model and draw them in increments of time that range from 1-15 minutes.
“I started running the drawing sessions because I really like having drawing from life once a week as part of my life. It gives my life a continuity, and as an experience, it’s extremely grounding. You’re sitting there for this chunk of time, you shut the f–k up. You’re staring at a person, and they’re nude, so they’re kind of exposed, but they’re really present. Everyone is really, really present.”
For Chiarello and the artists who frequent the group, the experience offers an opportunity to practice mindfulness and to work in a spirit of togetherness –– the artists and the model all tapping into the same creative energy.
“Jonathan Hodges said that what he missed about studying at an atelier was when everyone would be quiet, and you’d hear just the scratching of the pencils. It would almost sound like scribes in a monastery – everyone really quiet, but engaged and dedicated.”
In a figure drawing session
“Solidity,” oil on panel, 12” X 24,” by Jamie Chiarello
Chiarello has struggled to keep the sessions going over the years, facing housing insecurity she attributes to the rise of Airbnb. But as of 2025, artists gather every Thursday in her current uptown living room and studio, which is lovingly and harmoniously cluttered with art supplies, books, and the fruits of many past drawing sessions.
Of her current home and studio space, she says, “To me, clutter feels very human… I feel like the thing that’s taking over is a very corporate spirit that’s sterile – homogenous, without any character, any deviation.”
Jamie Chiarello surrounded by her work in her studio
Even more than a rise in barren, homogenous aesthetics, Chiarello, like many artists, considers AI to be the most existential threat to creativity. She compares the current climate of anxiety around AI’s capabilities to pre-Katrina years, describing the knowledge that we are all living on the precipice of something that will come to be seen as the end of one era, and the start of another.
Grappling with this uncertainty, she describes her response, “I’m just trying to find, how do I hold onto being human?”
Currently, Chiarello’s experiment in this endeavor is doing portrait studies in Jackson Square. Her sign reads, “Sit for a 15 minute portrait study, I don’t have to flatter you, you don’t have to buy it.”
“All we’re agreeing to when someone sits down is, you give up 15 minutes of your life, I give up 15 minutes of my life—that’s a fair trade.”
Chiarello talks about how despite how the sign may come across, she does feel competing impulses when drawing her subjects, one of which is to flatter them. She meditates on the idea that this desire to portray all people as beautiful is rooted in the innate beauty of being human together.
“I don’t feel like it’s flattery, because everyone’s f–king beautiful and interesting. When I know we just have these 15 minutes, I’m flooded with so much information about everyone’s humanity. Everyone’s humanity is profound.”
Sometimes, Chiarello will love the end result of the 15 minute study, and the sitter will not, and vice versa. She tries not to make any value judgement about the study that the sitter can perceive.
“I’m having my own experience, but it’s also really important to me that they have their own experience, and we both allow both of our experiences to be honest and true to what they are.”
She says the majority of the sitters come away with the same ambiguous impression— “I think they enter into the spectacle of, ‘wait, that’s kind of me? But I am ultimately something that is uncapturable.’ And that’s really the truth of it.”
One of her most memorable portrait study experiences was with a middle-aged transwoman adjusting to gender-affirming hormone treatment, who expressed apprehension about how she would present in the portrait study.
“I told her, ‘Look, you have a ton of faces, and you’ve also had a ton of other faces when you were a baby, and a child, and a teenager. You went through all these different people, and they’re still somewhere in you. The person at the grocery store and your best friend and everyone sees you differently. Whatever I’m showing you here is not definitive.’”
Maybe the most valuable thing Chiarello provides in her portrait studies is the same opportunity for grounding she provides in her drawing group. “One thing I’m offering you is to just do nothing, sit here and exist. There’s not a lot of opportunity for that in this world.”
Passing her spot in Jackson Square, many are drawn in by Chiarello’s witty, handwritten signs. She says she’s a compulsive sign maker and they’re an important part of her persona – like Superbowl season anti-capitalist admonition with a local flair, “Less yachts, more y’ats.”
Jamie Chiarello at Jackson Square earlier this fall, photo by Ellis Anderson
Chiarello sees her placement on the square, a public space defined by its constant flow of tourists, as an opportunity to platform her most urgent views.
“I think of it as a vortex, all of these people from all over the world in this one little moment. It’s constant changing over and over… but if you’re working there, you’re stationary. From that perspective, I have this opportunity to broadcast something… If I could say anything right now, to everybody, what would I want to tell them?”
Chiarello’s early signs always read, “Who are you?” Her latest message to the general public of Jackson Square an Antonio Gramsci quote, “The old world is dying, the new world is being born. Now is the time of monsters.”
Of her style, Chiarello describes melding the influences of classical western tradition and a more spontaneous, subconscious approach. Her commitment to drawing from life reflects her respect for the approach of the old masters, like Rembrandt, who she cites as the artist that reinvigorated her interest in Western Art History.
Chiarello finds a sense of comfort, community, and continuity in taking inspiration from the past. “Tradition doesn’t seem like an ugly thing to me anymore. It’s exciting! It’s 2025, and I’m working on this oil painting and the hand movements I’m making, the way that I’m engaging is not that foreign to like what Rembrandt would be doing.”
One of Chiarello’s paintings on the fence at Jackson Square, photo by Ellis Anderson
She still pulls from her subconscious in her work and sees how far her pieces diverge from what is considered traditional, observation-based renderings. One technique Chiarello employs is random mark making, from which she explores and expands upon any images she sees, like a Rorschach test. She calls this her “f–k around and find out approach.”
“The downfall of that is you don’t know if you’re going to get a decent painting or not but then the fun of it is that you don’t know!”
“A Thin Line Between Terror and Awe,” oil on panel by Jamie Chiarello
“The Center Cannot Hold,” oil on panel by Jamie Chiarello
Chiarello insists Jackson Square needs some young blood. She welcomes Gen Z to help steward that thriving ecosystem, as the threat of the new world’s monsters looms on the New Orleans horizon.
In a world that seems on the precipice of dystopia, Chiarello’s practice feels like powerful resistance to the forces that attempt to strip away what it means to be human. She straddles the new world and the old, tradition and experimentation, beauty and imperfection—all from her perch in Jackson Square, a vortex of energies and influences.
Her message, through handwritten signs, portraits studies, grounding group drawing sessions, is that what stands in opposition to monsters is always humanity – and community.
See more of Jamie’s work on her website and follow her on Instagram and Facebook.
Jamie Chiarello at Jackson Square in September, photo by Ellis Anderson