World-renowned artist Ruben Toledo is being honored with the special Icon Award in 2026. Today, we pause to hear from Ruben as he reflects on his enduring influence across art, fashion, and culture — with a heartfelt reminder of his late wife Isabel’s indelible spirit and vision that continues to inspire.
Where do you begin when starting a new illustration: story, silhouette, color, or emotion?
For me it all starts with "feeling" … whatever triggers my heart to feel a sensation: it can be a sound, a shadow, a glance, an aroma, an idea, a word or phrase.
From that first powerful spark of emotion then erupts the image. The story flows effortlessly like lava, the colors bloom by chance. I love that my work can still catch me by surprise after all these years. I’ve been blessed to collaborate with the best brands and makers in the world whether Louis Vuitton, Nordstrom, Tiffany, Estee Lauder, Barneys New York, or Target. They have always trusted my instincts to render their authentic and unique core essence because it is a sincere and reciprocal exchange.
As someone who bridges fashion, art, and culture, where do you see the most exciting opportunities for collaboration today?
Opportunities are endless now because we have all become so savvy to art and creativity. We expect our life to be naturally enhanced by art, fashion and culture on every level. Fashion is everywhere even in our toothpaste; it completely surrounds us because it is the heartbeat, the temperature, the shared language of our times.
We expect delight and inventiveness in our everyday experiences from the coffee or matcha we drink to our clothes, our music and entertainment, our homes, our travels, and adventures near and far. Despite the current upheavals and chaos we are now living in a whole new era is about to bloom into a new uncharted territory which will need all our collective creativity/humanity and our collaborative spirit to succeed and flourish. We will be shaping our renaissance. Life is now one great big, astounding collaboration.
How does culture — especially New York — shape your aesthetic perspective?
New York City thrives on culture!!! This has rare essence shaped me/us/the Toledos completely. I was blessed to meet and fall deeply in love with my Isabel at 13. Love is a powerful force which amplifies and elevates all human experiences. Combine our romantic love with our shared love for life- love for art, creativity and inventiveness – in all its manifestations – and you understand how we felt we created paradise on earth for ourselves, in the center of the city at the center of the world of culture!
What does authenticity mean to your brand in the era of AI growth?
Authenticity is more essential than ever. People can feel what is sincere and genuine because it touches our emotions. Nothing can embroider itself into our soul like an emotional connection. AI is splendid for conjuring visuals and can be very inventive in its marvelous randomness and chaos, but our human heart is a rare gem. That has no end to its glorious beauty and which instinctively responds to authenticity and thirsts for truth on all levels.
What still surprises you about fashion?
Great fashion always delivers the element of surprise! I am always bewildered by the perpetual inventiveness and the inspired ingenuity that fashion contributes to our culture. It is truly astounding in its power and reach. Every new generation creates their own design language and invents a new future. As an artist, this it is always exciting to witness a new era emerging.
When you designed the American Image Awards statuette a decade ago, what did you hope it would symbolize? You worked on the statuette so closely with your lovely Isabel. How was her influence manifested in the final piece?
We wanted to capture the stamina, the collective human effort of creativity. Our inter-contentedness which makes us all a much stronger creative force.
Isabel’s rare, gentle touch and sensitivity to humanity and along with our combined heroic group effort is evident in every curve and coloration of the statuette. Its powerful, circular force with no beginning and no end reflects the centrifugal force of nature that she was: quiet and oh so powerful.
Get your tickets to support Ruben Toledo and the future of the industry! We look forward to an incredible celebration on April 21!