Careful preparation and a mindful approach set the stage for capturing the essence of a sitter.
by Oliver Sin
Drawing the human face is an act of devotion, a practice that transcends mere technique and enters the realm of the sacred. It’s not laborious work, but it is a labor of love—a journey into the very essence of what it means to be human.
There’s no easy path to mastering the art of portraiture, no shortcuts to capturing the complexity of a face, but this challenge is where the beauty lies. For me, the human face is the most profound subject one can study. Each face is a universe of shapes, lines, and spaces, an ever-changing landscape of emotion and experience. No two faces are the same, and even the same face—in different lighting or different moods—offers an endless array of stories waiting to be told.
I find myself drawn to the creation of portraits that capture not just the likeness but the very spirit of the person before me—their joys, their sorrows, their resilience. In the rush to perfect technique, it’s easy to lose sight of the heart that must beat within the work. Technique alone is empty, devoid of meaning, but emotion without the means to express it is equally futile. The two must intertwine, like the threads of a tapestry, each supporting the other to create something truly alive.
Demonstration: Ruben
I vividly remember the day I met Ruben, in Mexico City, where he modeled for one of my workshops. He had once been a soldier, but a tragic diving accident left him paralyzed. Despite this, Ruben exudes a quiet strength and a deep well of gratitude that permeates every word he speaks. He lost his wife during the pandemic, yet he continues to give thanks for the life he has—a life marked by profound loss and enduring hope. As I drew his portrait, I felt the weight of his story and the resilience that radiated from him. The piece became more than just an image; it was an act of honoring Ruben’s spirit by capturing the quiet dignity of a man who has faced unimaginable challenges with grace.
Step 1: I started by drawing an outline in vine charcoal on a sheet of drawing paper. The medium-textured surface allowed the charcoal to blend smoothly as I worked. I carefully used contour lines to define the shapes and planes of the head first, since they’re the structural foundation of the portrait, providing the underlying framework upon which all other details are built. I took extra care to ensure that the initial drawing was solid and well-proportioned before moving forward with any additional details.
Step 2: Once the structure of the head was in place, I moved on to darkening the darkest shadows. I focused on the baseball cap, using the side of the charcoal stick to cover the area with broad strokes. I ensured that the shadows appeared deep and intense by pressing down hard on the paper. With the same broad strokes, I darkened the cap, the darkest shadows on the face, and the shadows around the neck, establishing a strong contrast in these areas.
Step 3: I focused on the eyes next, which are crucial to conveying Ruben’s sad expression. A skin fold forms above the eye as the eyebrows arch upward and gather toward the middle, while the outer corners curve downward. This angularity gives the eyes a less alert, more withdrawn appearance. Using the broad side of the vine charcoal, I applied the dark tones of the darkest shadows around the eyes. Then I filled in the eye sockets and facial hair with mid-tones to ensure a balance between the light, mid-tone, and shadow areas.
Next, I rendered a characteristic pout to further emphasize his sadness, with the upper lip appearing unnaturally long and dropping off quickly at the corners, while the lower lip slightly thins. The corners of the mouth also turn downward, lengthening the “long face” so typical of sadness. The eyebrows also play a critical role; their oblique angle signals grief, with the inner corners raised and drawn together, forming horizontal wrinkles in the center of the forehead. The folds of skin near the middle of the face are pulled up, while those closer to the edges are pulled down.
Step 4: I indicated tonal variations across the light areas of the subject and maintained the three values—light, mid-tone, and shadow—throughout the drawing to create depth and dimension. Tip: Squinting your eyes helps you see the values in a drawing more clearly. It simplifies the image by reducing details, making it easier to focus on the light, mid-tone, and dark areas. This allows you to better judge the overall balance of tones in your work.
Step 5: I darkened the hair using broad strokes of vine charcoal, pressing down harder to emphasize the mid-tone areas beneath the right cheek. I blended the shadow on the neck into the side of the skull, creating a smooth transition that unifies the portrait. I used my fingers to soften the outer edges to ensure they stay soft and neutral. I treated both the inside and outside contours of the facial hair as if they have no definable edge, rendering them like smoke to keep them soft and out of focus. I avoided drawing the facial hair as individual strands, aiming instead for a cohesive and realistic texture.
Final Step: I used a kneaded eraser, shaped to a point, to pick out highlights on key areas such as the pupils, eyelids, tip of the nose, eyebrows, and lighter parts of the face—especially under the eyes. I also created highlights in the facial hair, ensuring those details stand out subtly yet effectively. The sharp corner of the vine charcoal stick was employed to strengthen some focal points, adding clarity and emphasis where needed. I completed the portrait by carefully adding some character-defining wrinkles to bring Ruben’s face to life.
More Portraits by Oliver Sin
About the Artist
Oliver Sin is a Signature Member of the Portrait Society of America. He teaches drawing classes in the School of Fine Arts and 2D Animation, at Academy of Art University, in San Francisco.
