June 1st, 2021

Fred Calleri approached the minivan he’d seen a hundred times before in the carpool line of his son’s school. He took a deep breath and practiced the words in his head, formulating the question that would change his life forever, all the while wondering: what is the least awkward way to ask a complete stranger if I can paint their child?

Close to eight years before Calleri ever spotted his muse, he was just beginning his artistic career as an illustrator and graphic designer. He was always the artsy kid in school, but external pressures had him doubting the practicality of a career in the arts. As his father would say, “that’s lovely son, but you’re going to have to get a real job.” So Calleri joined the military, all the while secretly hoping that his time in the military could pay for him to go to art school. Two short years after enlisting, Calleri realized this goal by attending the Maryland Institute College of Art. There he majored in graphic design and worked towards becoming an illustrator. While working his 9 to 5, Calleri made sure that regardless of what living space he was in, he could find a way to create, whether that meant a makeshift studio in an apartment closet or in an old maid pantry. 

It was around this time that Calleri started scanning his favorite art magazines with a little more fervor. One thing that he noticed, flipping through the pages of his favorite magazines, was that the artists and galleries he most admired were predominantly based in the American West. “I was seeing painters that I couldn’t believe,” Calleri remembers, “and I thought, ‘Oh! That’s where the real pros are. That’s where the galleries that I want to get into are.’” Inspired to finally chase down his dream of becoming a full-time artist, Calleri packed up his life and moved out West, closer to the artists he admired and the galleries he aspired towards. There in a 1930s dude ranch in the woods of Flagstaff, Arizona, Calleri worked every minute towards his goal. A few years later, he found his way into his first little art gallery in Scottsdale: small, but a start. 

At the time, Calleri was painting realistic Western themes. drawing inspiration from his great American idols, NC Wyeth, Norman Rockwell, and Andrew Wyeth. Then one day, holding a 4” x 7” color film photo of John Singer Sargent in one hand and painting with the other, Calleri had a breakthrough. He was tired of squinting at this photo, tired of portraying it with realism. So in a radical act of curiosity, he pushed apart the eyes of John Singer Sargent and elongated the portrait’s neck. In short, he painted the figure in his now signature quirky distortion. “When I did that,” Calleri remembers, “that’s when the galleries called.”

When a friend of Calleri’s first saw this newly distorted Singer Sargent portrait, she exclaimed  that it was her favorite painting he had ever created. He remembers her getting to the heart of why: “It shows you personally,” she had said, “I finally see you now.” Through distortion, Calleri had touched on a greater reality than realism: artistic authenticity.  

Several galleries and a move to Santa Barbara later, Calleri received a call from Gallery MAR owner, Maren Mullin. “She kind of plucked me out of the sky,” Calleri recalls. At the time, he had no idea how long Mullin’s gallery had been open, or rather if it was open (it was not yet open at the time). It wasn’t until years later that Calleri learned that he was one of the very first artists Mullin had called before opening her gallery in 2008. Calleri professes, “Maren could not have been a better person for me to run across at that time in my career. She is such a cheerleader and a go-getter. She’s so professional, smart, kind, and loving.” With support from gallery owners like Mullin, Calleri felt emboldened to experiment more with his style and subject matter. Gradually, he began painting less of the Western themes and more of the vintage themes for which he is now renowned. 

A few years after finding representation at Gallery MAR, Calleri first spotted the muse who changed his life. Every day, Calleri would wait in the carpool line outside of his son’s school, waiting to pick him up at the end of the day. From middle school to high school, Calleri sat in this line, watching the droves of children in hoodies, skinny jeans, sneakers and graphic tees, file out of their school building and into the waiting cars. Through the monotonous crowd of 2010s fashion, one girl emerged wearing head-to-toe 1930s vintage attire. 

Each and every day that followed, this girl would walk to her mother’s car in full Great Gatsby-esque attire, from handmade feathered headdresses down to dazzlingly embroidered flapper dresses. Utterly charming in her full vintage garb, she looked like she had stumbled out of a Fitzgerald novel, or perhaps out of one of Calleri’s own oil paintings. Calleri couldn’t help but marvel, not only at her detailed dedication to the era, but also at her courage, expressing herself in a way so contrary to her peers. “So not only am I thinking, ‘what a strange, beautiful creature,’” Calleri chuckles, “but I’m thinking, ‘what guts it takes at that age to hold your head high wearing full vintage clothing while all the rest of the kids look like Justin Bieber.” Calleri knew then that he had found the greatest muse he could ever ask for, one who felt right at home in the wonderful whimsical worlds of his canvas. 

A few days before his son’s graduation, Calleri resolved that he must ask if he could paint this daring child. Gathering his courage, he made his way towards the minivan he had seen pull up hundreds of times before. Steeling himself for the moment, Calleri tapped on the minivan’s window. As the woman inside rolled her window down, Calleri blurted out his question before he lost the nerve: “I’m an artist who paints vintage portraiture, and I would love to paint your amazing daughter. Here’s my card. Can you take a look at my work and let me know what you think?”

The woman stared back at him quizzically before realization dawned over her face, “Oh, I know who you’re talking about… but that’s not my child,” she said. Calleri was dumbstruck. He had gone to the wrong minivan. The woman drove off and Calleri was left standing there, sorely disappointed and slightly embarrassed. His son graduated high school a few days later, closing the window for Calleri to ever see his potential muse again.

That is until a chance encounter one month later. Calleri and his son were eating pizza in a little Italian restaurant when in walked the same strange, beautiful child. Calleri rushed to greet them and pulled the parents aside. Out of earshot of the child, he told the parents his story, gave them his card, and once again, posed his question. 

A few days went by with no response, until finally one day, the phone rang: “We’re in,” they said. So began Calleri’s most fruitful artist/muse relationship. His new muse’s name was Iris. 

The first time Calleri photographed Iris, he was determined to make it as fun an experience as possible for both the girl and her mother. He was worried that this young teen would grow quickly bored of their photo sessions. To remedy this, Calleri encouraged her to bring her friends and to collaborate with him on the settings, the styles, and the poses of the shoot. To his great relief, Iris was anything but bored. In fact, it seemed that she not only tolerated their photoshoots but truly enjoyed them, bringing new ideas and exciting vintage fashions to every shoot. Calleri remembers being blown away when she showed up for a pilot-themed shoot with accessories Calleri had only dreamed of finding in old photographs: a vintage leather helmet, goggles, and a backpack. No longer did Calleri depend on found photos for his Jazz Age paintings. Instead, he had gleefully discovered the ultimate primary resource and infinite well of inspiration in this singular young muse.

What Calleri saw in his muse has certainly struck a chord with his collectors. “In essence,” he beams, “every painting I’ve ever done of Iris has sold. It’s not me that’s resonating with people, it’s her.” Calleri was so inspired by their photoshoots that he even began to alter his signature style to better suit his model. While many of the paintings he created based off of these photoshoots still featured his signature quirky distortion, he felt compelled to also begin capturing the real beauty of his muse, without distortion.

Looking back, Calleri remembers being just as excited to meet his muse’s mother, Tina, as he was to meet his muse. He had thought, “This mother has to be very cool to have a child that dresses like this every day.” Just as he had admired the child’s courage to boldly express themselves, so did he admire the mother who supported and encouraged their child’s self-expression. 

“Iris was unique from the get-go,” Tina remembers, warmly. She explains how she began expressing herself through fashion and art at an incredibly young age. As early as elementary school, Iris began fashioning her own clothes. She would make feathered headdresses from stuffed roosters she found on sale or fashion little swinging bird cages into a headpiece. Tina laughs lovingly, remembering a stage Iris went through in middle school where she wore clip-on cat ears every single day. She remembers other parents asking her why she let her daughter express herself in this way. The answer, to her, was simple: “Because that’s what Iris wants to do.” It had never occurred to Tina to encourage or discourage her daughter’s self-expression. Instead, she remembers thinking, “it was just Iris being Iris, this really interesting little person in my life.”

At the time, Tina was unaware that Iris was getting bullied at school for her vintage ensembles. It was only later that Iris shared this experience with her mother. Nevertheless, she never let it diminish her creative ambition. “Her desire to express herself was more important to her,” Tina explains.

Iris’ interest in vintage fashion began like any one of her creative endeavors: with a found object sparking an idea for an incredible work of fashion. One day in a consignment store, Iris had found a beautiful bubble gum pink chiffon prom dress. She saved up all of her money until she had enough to take this dress home. Pairing the dress with Victorian boots, she confidently wore her ensemble to school. “She really didn’t care what anybody thought,” Tina remembers. Her taste and style evolved until Iris began exclusively wearing vintage garb. “In high school, she became even more sophisticated with her vintage fashion and could hone in on a particular era, even down to the undergarments. There was no “Hanes Her Way” for Iris,” Tina jokes, “it was vintage everything. Even when she came home, she was not slipping into yoga pants and a t-shirt. It was vintage all the way, all the time.” 

Because of her daughter’s adoration of everything vintage, Tina remembers feeling instantly connected to Calleri’s work when he first approached her with his proposal to paint her daughter. Scrolling through his website, Tina had thought, “of course he wants to paint my child.” To her it made perfect sense. Entranced by Calleri’s whimsical, nostalgic style, she could see right away how her beautiful, vintage-loving daughter would shine through the canvas, harmonizing brilliantly with Calleri’s work. “It was honestly a match made in heaven,” she says.

At the time that Calleri entered their lives, Tina’s father — a prominent figure in both her and her kids’ lives — was dying of cancer. Their days were heavy with the weight of this pain. In contrast, Calleri’s cheerful paintings and kind, fun-loving spirit became an especially welcome reprieve for their family. “It was all of the sudden this really fun, bright, happy spot in our lives,” Tina remembers, “Fred was observing this child who my father and I thought was magical… and Fred agreed. It was a delight to have this other figure step into our lives and say, ‘oh yeah, that kid’s special. So special that I want to paint her.” The first painting Calleri ever painted of Iris was a beautiful portrait sketch for Tina’s father. Tina remembers the sketch warmly, “We got to present it to my dad, and he just treasured it for the few more months that he was alive. For us, it was like a breath of fresh air.”

When Tina’s father passed away later that year, Calleri was right there by the family’s side, organizing the memorial service materials and going on long walks with Tina’s stepmom. He stepped up for the family in their darkest hour. Shortly after her father’s death, Tina and her husband split up. “I was trying to get my sea legs under me and figure it all out.” Tina recalls, “Fred was just this very steady friend, helping me navigate some treacherous waters. He’s the kind of guy who shows up every day and really helps put a positive spin on everything.”

Perhaps this relationship between artist and muse, albeit incredible and fruitful, would have fizzled over time, if it weren’t for one beautiful, unexpected twist: After months and months of getting to know this family, Fred Calleri and the mother of his muse fell in love.

“Our lives kept intersecting and our connection continued to grow,” Tina says. Calleri stood by Tina’s side throughout her family’s hardships and became the family’s safe, happy oasis. “Ultimately, I can’t even tell you when it became a romance instead of a friendship,” she says, “it was just this seamless strengthening relationship.” Even more endearingly, Calleri truly saw and cherished her daughter for exactly who she was. Tina could see that Calleri saw Iris through the same lens that she did: one of proud admiration, respect, and understanding. “That spoke to me,” Tina recalls, affectionately. 

This perspective became especially important to Tina a few years ago when her beautifully unique child, Calleri’s young muse, came out as transgender. Iris’ name is now Simon.*

Simon’s early exploration of and adoration for vintage women’s fashion is part of the reason that Tina was so surprised when Simon came out as transgender. Throughout his early life, Simon presented in “an extremely effeminate way.” When Tina asked Simon about this, his explanation was more than understandable: he was simply trying to figure out who he was and how he wanted to express himself, like any teenager would. “I think that’s the thing,” she agrees, “Simon was really searching for some kind of expression of himself.”

Ever since his transition, Tina has noticed a huge difference in Simon’s happiness levels: “Simon before the transition was wonderful and magical, but he was also serious and very inward,” Tina muses. Looking back on the hundreds of photos that Simon and Calleri took together with fresh, knowing eyes, Tina can see now just how seriously Simon took his modeling job. Throughout each shoot, Simon was remarkably unself-conscious, but also painfully professional, despite his young age. “Each photo was more exquisite than the last, but there was also never any monkeying around or being silly,” Tina recalls.

Now, Simon is a far happier person and has gained quite a few close friends, whose genuine support has helped him connect more deeply with others. “He’s become much more outward and really wants to connect,” Tina says, “I see how his transitioning was the right thing to do. I’m so grateful because now he has the ability to be entirely authentic.”

Simon has been transitioning for years now, but a year and a half ago, he had his top surgery. Calleri was inspired to create a painting in honor of this step in his transition. Occasionally, Simon would come by to check on the painting’s progress, while recovering in the room right next door to Calleri’s studio. The painting is entitled “Ebb and Flow” and features a portrait in front of a large vintage map labeled “Map of Discovery.” On the map to the left of the viewer lies a mermaid and on the right, a Zeus figure. In between these symbols of femininity and masculinity stands the Simon that Calleri met at age 14, in one of his classic vintage ensembles. The painting pays homage to the person Simon has always been, an expressive, unique individual, on an ever-evolving journey of self-discovery. 

A few months ago, Calleri received an email about a man in Boston looking for available work from Calleri. The collector had just purchased a painting of Calleri’s and wanted to know if he had any paintings with male figures in them. Up until that point, with young Simon as his primary muse, Calleri had not painted very many male-presenting figures. So he passed along images of the few pieces that he had created: one of Vincent van Gogh, one of Sitting Bull, and one of Theodore Roosevelt. Calleri then sent along an image of the painting in Gallery MAR Carmel, “Ebb and Flow” and explained the painting’s significance. The collector and his husband bought all four works. 

Shortly after, Calleri received an email from the collector: 


Hi Fred, Tina, and Simon,   

My husband and I love the paintings. Thank you, Fred, for your incredible work. I thought I would send you a picture of where “Ebb and Flow” is hanging in our home. We put it by the front door to remind us to be true to ourselves no matter where we go in our life. The painting will make me smile every day. 

Simon, from what Fred has shared, you have the individualism of Van Gogh, the courage of Sitting Bull, and the integrity of Teddy Roosevelt. I hope you never lose those qualities. For us, these four paintings will always be a set. I wish I had the self-awareness and self-respect that you have when I was your age. I think this may make me the proud owner of the largest all-male collection of Fred Calleri works. I am counting “Ebb and Flow” in there as I will think of and call that figure… Simon.

All the best, 


With tears in his eyes, Calleri read this letter aloud to Simon, touched by this stranger’s kindness and profound understanding of Simon. After all, it is these very same characteristics in Simon that inspires Calleri the most. “The depth of Simon is so intense.” Calleri reflects, “It’s been a real change in my life to even know him. You meet him and you just think, somebody sprinkled stardust on that person. Basically, I found a magical human.” 

While Calleri plans to continue painting from the hundreds of reference photos from him and Simon’s photoshoots over the years, he also looks forward to painting Simon as he presents himself today. “Simon and Fred have a pretty special relationship,” Tina says, proudly, “Fred really admires the artist in Simon and vice versa.” She has confidence that the two of them, connected by their mutual respect and admiration for each other’s artistry, will continue to find paths towards artistic collaboration.

Much like his relationship with his muse, Calleri’s artistic style is continuing to evolve. Calleri has been inspired to be more daring and experimental with his work of late. Through dynamic brush strokes, powerful color, and expressive texture, Calleri works towards even greater sophistication in his paintings. “In a sense, I want to elevate my style. I’m in a really experimental phase where I’m trying to be more powerful with color and texture. This is me pushing out a little further, and I can’t wait to see where it leads,” he says. All those years ago, Calleri’s first artistic breakthrough was in finding a truer expression of himself through quirky distortion and whimsical worlds. Now, inspired by Simon’s individualism, courage, and integrity, Calleri dares to express himself as boldly and as vividly as his magical muse. 


We would like to extend our deepest gratitude to Fred, Tina, and Simon for sharing their beautiful stories with us. While Simon preferred not to provide an individual interview, all details and photographs were provided with his full permission. 

*The name Iris is a pseudonym as Simon asked that we not reveal his deadname

Written by Veronica Vale