Donald Robertson Headlines the Costume Council’s Fashionably (Un)Dressed Evening

On May 8, the Costume Council of the Chicago History Museum hosted “FASHIONABLY (UN)DRESSED,” a cocktail-filled celebration and conversation with fashion’s most irreverent artist: Donald Robertson, better known online as Drawbertson.

The event brought together a sharp crowd of tastemakers, collectors, and creatives for an evening of visual wit and aesthetic rebellion. Robertson was joined in dialogue by acclaimed designer Alessandra Branca, as the two unpacked the artist’s expansive, high-gloss career.

From the opening remarks to the last laugh, Robertson lived up to his reputation as fashion’s jester-king. “What a treat to present Donald Robertson, the Andy Warhol of Instagram,” said Karen Peters, Costume Council Program Chair and event co-chair.

The Artist Who Rewrote Fashion’s Visual Language

Donald Robertson doesn’t just illustrate fashion. He distills its essence, then explodes it across canvases, dinner plates, and even walnuts.

A former creative director at Estée Lauder Companies, Donald Robertson launched his career in beauty at MAC Cosmetics. There, he helped create VivaGlam!, a campaign that raised millions in the fight against AIDS. He went on to hold creative roles at Marie Claire, Cosmopolitan, and Glamour, bringing a graphic sensibility that predated the content-creator era.

In the 2010s, everything changed. His assistant set him up with an Instagram account. The feed, filled with cheeky portraits of fashion royalty like Anna Wintour and pop culture icons like Beyoncé, quickly went viral. In 2014, the Council of Fashion Designers of America took note, nominating him for “Instagrammer of the Year.”

He’s been Drawbertson ever since.

Fashion Meets Pop Art and the Crowd Loved It

At the Costume Council event, Donald Robertson was in conversation with designer Alessandra Branca, one of the evening’s honorary co-chairs alongside Kimberly Gieske Robertson. The duo’s back-and-forth was equal parts design talk and insider banter.

For Artist’s Circle patrons, signed copies of his newest art book, Sofa King Great, served as luxe party favors. The 400-page volume, released under his @drawbertson moniker, showcases a whirlwind of paintings, sculptures, and globe-trotting musings.

It’s not a book so much as a visual autobiography of a life lived in high color.

A Custom Unveiling for Chicago

One of the night’s highlights was the unveiling of a custom piece Donald Robertson created exclusively for the Costume Council, a vivid work blending the spirit of Chicago fashion history with his signature iconography.

Part auction item, part spectacle, the artwork was as much a conversation starter as the artist himself. Patrons lingered around the display, champagne in hand, debating its references and reaching for their phones.

“Donald Robertson is a prolific illustrator and pop artist whose work spans both industries and media. Whether he is painting walnuts or Birkins, you can always spot a piece of his art,” said Karen Peters, the Council’s Program Chair and event co-chair. “His work is so playful and fun, and he was truly marvelous to highlight our collection for our invitation and auction.”

Indeed, his pieces, whether painted on canvas or silk, radiate a certain mischief. Even the most storied brands, from J. Crew to Mark Cross, have embraced his colorful chaos in capsule collections.

From Hudson Yards to Palm Beach

Donald Robertson’s creative reach extends well beyond fashion week. His art has graced Hudson Yards, Cadillac installations at Art Basel, and even high-end home collections in 11 European countries via Westwing.

And then there’s Barbie. Yes, that Barbie.

He redesigned the official Barbie Style Guide, a playful twist that delighted the Mattel brand and fashion insiders alike. This is, after all, a man who can make walnuts fashionable.

An Evening That Left a Mark

The Costume Council’s Fashionably (Un)Dressed evening wasn’t just an art talk. It was a moment of cultural cross-pollination. A place where fashion met fine art, and creative legacy reflects the evolving role of fashion in how we tell stories, through art, through people like Donald Robertson.

By the time the final cocktail was poured, it was clear: Robertson doesn’t just sketch fashion. He reframes it, reinvents it, and, with a knowing smile, dares you not to love it.