What Sandy Powell Taught Me About Personality Dressing

My first encounter with Caravaggio's genius wasn't in a grand museum hall, but through the passionate recounting of a dear friend. We were at the National Gallery, and he, whose intellect I deeply admired, was weaving tales around the allegories of love depicted in various paintings. I vividly recall that summer day, a tender memory from a time when moving to Milan, the birthplace of the very painter we discussed, was an unimaginable future. Now, having lived here for years, revisiting his works feels like a homecoming, a profound pleasure.

For that very same reason, I enjoy rewatching Derek Jarman’s Caravaggio, his fictionalized retelling of the Baroque painter’s life. What has always drawn me into Caravaggio’s paintings, beyond their sheer dramatic power, is their unflinching, intense realism. The mold on the fruits, the painful smirk on the boy bitten by the lizard, and the sickly green complexion of Bacchus – these visceral details draw the viewer in, into the very moment the objects were arranged or models were seated, ready to be painted.

Just last week, a memory resurfaced, triggered by an 'old' post on Sandy Powell's Instagram feed. She was seeking information on the whereabouts of a specific dress worn by Lena, played by Tilda Swinton, in Caravaggio. The image of the film still instantly transported me back to a pivotal scene in the film. It was a moment that, years ago, profoundly illuminated for me the power of costume as an instrument of knowledge.

Before that particular dress was gifted to Lena, I understood her role in the narrative. Still, her character felt somewhat adrift; her purpose in the unfolding story of the film was not entirely clear to me. But the instant Caravaggio presented her with that dress (that Sandy Powell mentioned on her IG post), it was as if a floodgate in my mind burst open. That costume’s very texture, its drape, perhaps the way light fell upon it, evoked a powerful visual resonance with the painter’s works. My mind immediately unlocked Caravaggio's masterful paintings of female figures, including Lena's own poignant portrayal of the Virgin Mary. In essence, Sandy Powell's costume achieved for Lena what Caravaggio’s brushstrokes did for his subjects: using powerful, evocative visuals to draw me into another realm of the film, one that existed beyond the mere celluloid, connecting me to the profound depth and spirit of Derek Jarman's vision. That single costume anchored Lena's character to the rich visual lexicon of the painter’s work. I learned that it was Sandy Powell's first assignment as a costume designer for a feature film, and she not only understood her assignment but also transcended it.

Recalling how I felt during the film, I am compelled to draw parallels with the philosophy of Manuela Pavesi, a figure revered for her unique and intimate approach to styling, whether for Vogue Italia or as a fashion coordinator for Prada. Manuela was always insistent that fashion must be associated with knowledge and curiosity. For her, a garment isn't a status symbol; it serves to tell a story. Ideally, the wearer should choose a garment that evokes a specific time period, a rich heritage, or piques our curiosity and aspirations. Manuela Pavesi's selections for her fashion editorials weren't just about trends and aesthetics; they were instruments of knowledge, narrating stories.

I deeply align with the approaches of both Sandy Powell and Manuela Pavesi in the fields of costume design and fashion. I have always believed that when our clothing fails to bridge us into the inner depths of our historical or cultural context, or to connect with our internal realm, it is, to me, little more than a sad piece of rag, regardless of its price tag. This is precisely why I am a strong proponent of building a wardrobe from a personality-driven approach. Dressing is not just about shapes, colors, or trends. We need to choose clothings that reflect our characters, our most authentic selves, and, crucially, our contextual selves – the profound connections to the heritage, culture, and people that have shaped who we are.

Just as Lena's dress unlocked a deeper understanding of Caravaggio, our clothing has the power to reveal and amplify who we are, to ourselves and to the world. What stories are your clothes telling about you? At 72 Smalldive, we believe in this power, and that's why we offer classes on building a Personality-Driven Wardrobe in our Elevate360, a transformative leadership program.