Kanye loved her – you will too: art appreciation, Diana Stelin-style

Boston-based artist, former Newbury Street gallery director, and founder of the Plein-Air Art Academy Diana Stelin is preparing to teach kids pop art in the spring. The Academy is also running a first-of-its-kind Pre-K/Kindergarten art contest with entries due March 31. In Mid-April, you can join the schools’ immensely popular plein-air painting event: Cherry Blossoms at Arnold Arboretum. And during ArtWeek Boston, on May 1, 4, and 5, Diana will run Warhol Poppies Kids Workshops at the Arboretum. The Plein-Air Art Academy’s children’s classes were voted Boston’s best on CBS Local in 2015.


A man walks into an art gallery. The gallery director smiles as she approaches. “Is there anything I can help you with?” she asks warmly. “I’m interested in that piece in the window,” he replies, pointing to a Jeff Koons balloon dog.

To get a better read on him, she casually asks him a standard gallery question: “Do you work in the arts”? “In a way,” he responds. “But on the music side.”

The plot twist: he is Kanye West – and she has no idea who he is. The year is 2007 and he’s just on his way to becoming a household name. While the girls in the back room squeal in disbelief, Diana Stelin discerns within moments that he is genuinely curious about art collecting and knowledgeable about art history.

Diana goes on to do what she does best: asks thoughtful questions, listens intently, and offers an ideal mix of art history and contemporary art world knowledge. In this high-end art space on arguably Boston’s most famous street, she makes interacting with the multi-thousand-dollar works of art a game.

Kanye buys the sculpture. He continues to work with Diana, who teaches him more about the art market and helps him hone his personal taste as he acquires important works by Andy Warhol and Damien Hirst. His assistant has Diana on speed dial and West writes on his blog, KanyeUniverseCity.com, “In Boston I went to one of my favorites galleries – DTR Modern Galleries.”

While at DTR, Diana also shares her expertise with actor Jason Biggs, singer Diana Ross, Brazilian model and TV hostess Luciana Gimenez Morad, mother of Lucas Jagger, and Italian soccer player Alberto Aquilani and his team.

Fast forward for a moment to Art Basel 2013, when six-month-old North West meets Jeff Koons, and Kim Kardashian captions the photo ‘Art lessons!’. One can’t help wondering whether Kanye knows that Diana is now doing just that: teaching art to children and adults with that unique, highly personal approach he was so drawn to.

From selling contemporary art to nurturing budding contemporary artists

With a BFA in Painting from Cornell University and a Master’s in Arts Administration from Boston University under her belt, Stelin helped owner Theodore Vassilev establish DTR Modern Galleries on Newbury Street in 2005 – and embarked on an art-loving jetsetter’s dream, travelling to the Venice Biennale, FIAC Paris, the LA Art Show and Art Basel Miami in search of new markets, talent and trends, all the while helping to grow DTR to include locations in New York, Palm Beach and Washington D.C.

She continued to juggle the demands of her career when her first son was born, and again when the second arrived 3 years later. But the direction of her passion for art began to shift. A firm believer that one can’t begin an artistic education too early, Diana searched for art classes for her kids – but found nothing in the Boston area to match her vision.

So, with her appetite for the next challenge growing in concert with a desire for a balanced family life, Diana bid farewell to her seven-year career in the contemporary art world – and dove into her new project: the Plein-Air Art Academy.

“I wanted an integrated, personalized art education for my kids, with art history interspersed with hands-on projects,” she explains. “The dream of opening an art school had been there for years, since I worked at the Nandi School of Art in New Jersey. I wanted to offer the Boston community – young and old – something I myself had lacked in my college art education.”

What could possibly have been missing from her Ivy League experience? “I envisioned a more rigorous and diverse artistic experience. When I was studying art in college, I don’t remember ever going outside to draw – even though Ithaca is a very beautiful place. Instead, we did four years of figure drawing. I wanted to get away from that,” explains Diana.

Her emphasis on getting students outside is equally driven by modern lifestyle trends. “Our kids are growing up in a video game and iPhone culture, and I wanted to help them find a different kind of escape through creativity and discovery. Art gives kids a natural way to relieve stress and process everything that happens in their busy lives.”

There’s plenty of science behind her philosophy. Art education has been shown to help pave the way for success in school, work and life by helping to enhance motor skills, literacy, language development, decision-making and critical thinking, and math skills. “When we work on joint projects like mural making, the kids sit together and discuss and plan what they’ll be doing. They engage all their senses and simultaneously develop important communication skills,” says Diana.

The plein-air concept also delivers another important benefit: natural daylight, proven to enhance overall well-being, concentration, and ability to learn. With Americans spending about 90% of our time indoors, every extra step taken outdoors matters.

In short, the Academy’s formula checks every box, combining a first-rate, personalized art education with small groups of similar ability levels with plein-air creativity to offer a unique, holistic method for developing well-rounded humans.

A handful of classes are even taught in Russian to accommodate Diana’s large Russian-speaking following.

The canvas: Boston’s best parks

Weather permitting, Diana holds her classes in diverse locations throughout Boston. Among her students’ favorites are Larz Anderson Park, the Chestnut Hill Reservoir, and the Franklin Park Zoo. Every semester also includes a museum trip.

The Academy also regularly hosts workshops and special events for students of all ages, including pastel landscapes at the enchanting Fens Kelleher Rose Garden – and a wildly popular annual Japanese inks and watercolors event, Cherry Blossoms at Arnold Arboretum, on April 14-15 (so far, nearly 1,500 have expressed interest).

“What I have always loved about what I do – both as a gallery manager and as an art teacher – is that I learn from every single person,” says Diana. “When you and I look at a Jeff Koons balloon sculpture, we see completely different things – and your kids will have a perspective on that piece that I will guarantee will surprise you. Everyone comes to art from a completely different background, and that’s what makes it fascinating – whether you’re Kanye West, a third grader from Belmont, or a busy parent who wants to make time for art, beauty, or a bit of mindfulness and relaxation in your life.”

Diana’s own home is a testament to her egalitarian approach, with Dali and Miro lithographs occupying the same prime wall real estate as her six-year-old son’s Monet-inspired landscapes.

 Making pop art popular among kids and teens

This spring semester, which begins on April 2, Diana is taking her students back to her gallery roots with a semester focused on pop art: Warhol, Lichtenstein and Keith Haring.

At Arnold Arboretum, they’ll find big blooming flowers and recreate them with oil pastels, using Lichtenstein’s dot series as inspiration. They will draw self-portraits mimicking Warhol’s Marilyn series. For Keith Haring month, Diana will take them outside, where one project will involve dancing on pavement, then lying down in a pose and coloring in the outlines to create life-size dancing figures.

As always, there will be scavenger hunts – and lots of storytelling. “Art history stories are like fairytales – and kids love fairytales,” says Diana. “In our Michelangelo unit, we talked about how in order to paint the ceiling, Michelangelo needed to build himself a really tall bed that he could lie on to paint.” What kid can resist such an image?

Diana’s teen students focus more on a single main project. “We experiment with a lot of different media so they can put together interesting portfolios,” says Diana. Whether the teens are preparing for art schools or adding eye-catching supplements to their liberal art college applications, the creative elements can help them stand out in the selection process.

Art for all

Always looking to broaden her horizons and share her passion for art with a bigger audience, Diana is currently running a first-of-its-kind art contest for Boston kindergarteners (entries due March 31), judged by elite professionals from some of Boston’s top art destinations.

And this summer, the Academy will run week-long art history themed camps for kids ages 6-12, covering the school’s most popular themes: Egypt, Greece, Bible Stories in the Renaissance, Japan, and Surrealism.

If only LA wasn’t so far away, it seems likely that North would be gearing up for outdoorsy art lessons, donning designer smocks and tracing Saint on the sidewalks come springtime.

But lucky for us and our kids, an art education fit for the stars – better yet, tailored to ordinary people and their individual tastes – is just around the corner. And it’s a walk in the park.

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