Artist and creative director Donald Robertson has built an illustrious career out of capturing the Zeitgeist. His paintings pair fast and furious brush strokes of exuberant colour with a laser-sharp focus on the intersection of fashion and pop culture. A master of motif, Robertson generates graphic signatures riff on dripping lips, sardonic designer logos, galloping horses and stylized cowboys, and his work has an #iykyk vibe that conjures a milieu of fashion VIPs, effortless affluence and iconic Americana.<\/p><\/blockquote>\n
![\"\"](\"https:\/\/sothebysrealty.ca\/insightblog\/wp-content\/uploads\/2025\/12\/INSIGHTSpring25_Artist01.jpg\")
<\/div>\n\u201cIt\u2019s almost like I\u2019m art paparazzi: I like to capture something that\u2019s happening right now,\u201d says Robertson, a prolific social media poster who has collaborated with prestigious fashion and beauty brands, upscale department stores and boutiques, and top newsstand magazines on a range of endeavours, from lipsticks and capsule collections to pop-ups.<\/p>\n
Last year, Robertson\u2019s paparazzi paintings included besties\/Olympic commentators Snoop Dogg and Martha Stewart, athlete\/tabloid regular Travis Kelce, attention-getting pop star Harry Styles, plus a mix of royals \u2014 of both the Windsor and the Hamptons sort. Collectors like Beyonc\u00e9 (or the fans who snap up his work practically as soon as it appears on his Instagram) can\u2019t get enough of it, and neither can the artist himself, a Canadian who now lives in Dallas, after stints in Toronto, New York, Korea, Japan,China and Los Angeles.<\/p>\n
\u201cI never wanted to be a starving artist,\u201dnotes Robertson, who started his career in the late 1980s after dropping out of Toronto\u2019s Ontario College of Art to work with then up-and-coming MAC Cosmetics.<\/p><\/blockquote>\n
<\/div>\n
At MAC, the young artist developed creative concepts that led to his love of iconography. \u201cThat\u2019s where the lips came from,\u201d he says of the glam motif he has slapped on countless canvases \u2014 a car, even a building exterior in Nashville.<\/p>\n
It also honed his instinct for finding the next new thing. \u201cI got my green card, moved to New York and started in publishing next\u2014 and that\u2019s where the celebrity obsession came from. My generation, we were putting celebrities on magazine covers, which was, at the time, unthinkable,\u201d says the father of five and a former creative director at top U.S. fashion magazines like Marie Claire,<\/em> Glamour<\/em> and Cosmopolitan<\/em>.<\/p>\n
\u201cI was in publishing for a long time and I got addicted to news leads. It was just something that was drilled into us. If something was news, newsworthy or new, it would hit. And that\u2019s always been something that I\u2019ve liked to incorporate into my art,\u201d he explains.<\/p>\n
Recently, that included chronicling pop culture\u2019s unofficial Family of the Year. It all began with a painting of Donna Kelce (mother of football and podcast starsTravis and Jason Kelce) as she spectated at Superbowl LVII, where her two sons played on opposing teams.<\/p>\n
\u201cI remember thinking at the time, This woman is incredible. And I painted her on a cereal box and called it \u2018Special K.\u2019 It was just something that captured a moment.She was new to my people, my followers, but likeable…so I painted her. Then she immediately reached out to get it. The next thing you know, she sent me a picture of her holding the box,\u201d says Robertson.<\/p>\n
This social media connection continued through the year. \u201cI sort of befriended the family. And when Jason was made [a finalist in People <\/em>magazine\u2019s] Sexiest Man Alive, they called me to do a painting of him to tease him; it created this whole news thing. Then Taylor Swift showed up and it was just \u201cGame on.\u201d It just exploded.So, it was a series of newsworthy things that became this really, really fun year of documenting the craziness that was the Kelce family and the Swifts.\u201d<\/p>\n
Robertson\u2019s visual hot takes have earned him 227,000 Instagram followers, many of whom are eager to snap up his art, much of which is made quickly and sells quickly.<\/p>\n
This immediacy \u2014 and the direct line to tastemakers, collectors and fans \u2014 is something Robertson has valued ever since his oldest daughter convinced him to grab an iPhone and venture onto Instagram.<\/p>\n
\u201cNext thing you know, I was having. back-and-forths with Carine Roitfeld and working with Colette,\u201d recalls Robertson, referring, respectively, to the influential former editor-in-chief of Vogue Paris<\/em> and the chic Parisian boutique.<\/p>\n
\u201cInstagram made the world very small and very accessible. It was wonderful andI got addicted to that community. It\u2019s changed and become a big giant beast, but there\u2019s still community. I\u2019m like an old dad and Marc Jacobs is popping onto myInstagram and liking stuff. \u201cWhen I was in [print] magazines, [that] would\u2019ve been virtually impossible.\u201d<\/p><\/blockquote>\n
<\/div>\n
While the artist is far from obscure now \u2014 you know you\u2019ve arrived when Assouline publishes an eponymous tome on your life and work \u2014 Robertson relishes the gatekeeping that social media dismantled.\u201cWhen I was young and hustling, I had a pain-in-the-ass portfolio that I had to drag to Europe. I had letters of introduction thatI had to hide when I was going through customs. And then people would cancel meetings…and by the time you finally got to meet with somebody, you were just so frustrated if it didn\u2019t go well. Those days are gone. It\u2019s been a great equalizer and it\u2019s been very exciting,\u201d says the artist who uses social media to showcase, and solicit, new work. (\u201cI\u2019m paying for college tuition with this stuff,\u201d he quips.)<\/p>\n
Over the years, Robertson\u2019s self-diagnosed \u201ctrend FOMO\u201d has driven him across America and Asia where he has designed global marketing campaigns\u2014 (he was senior vice president creative director at Est\u00e9e Lauder for several years),collaborated with renowned artists and brands and honed his art. But Dallas maybe where he takes a breather…at least for a little while.<\/p><\/blockquote>\n
<\/div>\n
Social media is now his favoured career conduit. \u201cIt\u2019s a way of doing my corporate job and incorporating my art at the same time. It\u2019s a nice overlap. Also, it\u2019s really hard to hustle content for Instagram. But if you can paint, it makes it so much easier.I don\u2019t have to go to exotic locations to get pictures. I can just paint them. I can literally create content all day long in my studio,\u201d he explains.<\/p>\n
Of course, the next paintable meme always beckons. As an example, Robertson recounts the story behind his Internet-famous Snoop and Martha Stewart series.<\/p>\n
\u201cWhen Snoop Dogg showed up at the [2024 Paris Summer] Olympics, at the equestrian event, in that tuxedo suit, I was just like, Where\u2019s my paint? Where\u2019s my paint? Maybe I\u2019ll just do the Olympic circles as smoke rings. Oh my God, that painting sold so fast. It was unbelievable.<\/p>\n
\u201cThen I did a picture of Martha withSnoop: the ultimate odd couple. It was just so sweet,\u201d says Robertson, who in December posted an Instagram photo of Stewart holding one of his sold-out Snoop paintings.<\/p>\n
After a four-decade-long career, Robertson knows to amplify a news hook when he sees one. \u201cThat\u2019s the kind of thing that creates community through your art. But it also makes something irresistible. You know whatI mean?<\/p>\n
\n