Basics of Painting Portraits in Acrylic, Watercolor & Oil

The Misses Vickers by John Singer Sargent, oil on canvas, 54.25 x 72.01.
The Misses Vickers by John Singer Sargent, oil on canvas, 54.25 x 72.01.

Portraiture is the genre of painting in which the likeness of a sitter or model is depicted by the artist. Historically, portrait paintings were often commissioned by the well-to-do or powerful, but artists will also create portrait art when they find a compelling model or want to commemorate a person with the work.

In the contemporary art world, portraiture as status symbol is less and less prevalent. Instead, artists explore portrait painting because of the challenges inherent in painting a person’s likeness while capturing their personality and spirit, and the pleasure in the pursuit of painting the human figure and face. Rarely are painted portraits judged solely by the accuracy of the depiction. Instead, artists try to eke out the emotional character on the visage of their model.

Compositionally, portrait art can vary—the sitter can be sitting or standing; clothed or nude; full length, half length, or a bust view of the head and shoulders; and depicted in profile, in a three-quarters’ view, or facing directly out. Portraits can be formal affairs, with figures in their best clothes and presented in commanding ways, but they can also be more informal with a slice-of-life feel that allow the viewer to feel as if they are seeing inside the private world of the sitter.

Throughout the centuries, portrait painting has been a reliable and sometimes very lucrative business for artists. Painters would often become famous because of their portraits, elevating their status in the wider world. Famous portrait artists include Diego Velazquez, Rembrandt, Ingres, Thomas Eakins, Anthony Van Dyck, and John Singer Sargent.

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The First Crucial Steps of Portraiture


0804herrdemo2_400x600.jpg 0804herrdemo3_400x600.jpgThe first step in portraiture is always meeting the client or model. Sometimes, if you are a professional, this can come through an agent, like a local representative of Portrait Source (a portrait broker).

The next step is to have a discussion on where the portrait should be set. Sometimes the client is “in charge” of this aspect of the portrait painting, as they are paying for the service, but sometimes the artist is in charge and places the model where he or she desires.

Often the best way of deciding where to set the scene of a portrait painting is to start looking through your viewfinder. From there you can, settle on a pose and take reference photos.

The best portrait artists allow their models inclinations to guide them in terms of the chosen pose or composition.Garth Herrick reflects on a recent portrait painting experience of his, when he was trying to decide where to have his three young sitters pose: “There were so many good choices for settings! It was amazing that we so quickly narrowed the pose down to the kids sitting and standing on the rock, considering that all areas of their place were just spectacular.”

The kids gravitated toward that particular rock. The client’s original idea was to have them sitting in a porch swing, which was nice, but it didn’t really inspire me, especially as there was a blank stucco wall behind the swing. I wanted more contrast with the kids’ white clothes. The dark evergreen foliage behind the rocks where we eventually settled was more interesting. I took a lot of pictures that day, and met with the clients to review the photos on my computer. We decided that we wanted to take some more photos. It was sunnier the second time, so the weather conditions became more of a challenge.

Once I settled on the reference photos, I spent a few days combining them into a composite image in Photoshop. All of the photos used in the composite image were taken on the second day because of the different lighting conditions on that day. I mostly worked in Photoshop the day after I took the photos, but I kept rethinking things and fine-tuning the image. Although the client approved my first version, I kept tweaking, and they approved each subsequent version.

From an article by Garth Herrick.

A Portraiture ‘Must’

illian by Wende Caporale, 2003, oil portrait painting, 7 x 5.Jillian by Wende Caporale, 2003, oil portrait painting, 7 x 5.

During her portraiture workshops, Wende Caporale takes a considerable amount of time to offer tips on drawing the human head accurately. “Even if you work from photographs in your portrait painting, it is very important to be able to draw well,” she tells her students. “You have to be aware of photographs’ inherent distortions and be able to adjust them accordingly. Furthermore, drawing skills are critical in making adjustments during all stages of the portrait painting process.”

Using a piece of vine charcoal, Caporale made quick drawings of members of the class to demonstrate how an artist can use the average proportions of the head to determine how a specific model’s features may vary from that norm. “The standard proportions divide the head into three equal units of measure from the forehead to the eyebrows, from the eyebrows to the bottom of the nose, and from the nose to the bottom of the chin,” she explained. “When you look at a sitter with the eye of a portrait painter you can judge how those relationships might be different, and that gives you a clue as to how to draw or paint a likeness. For example, if you recognize that the person’s forehead is larger than most, you can draw or paint it that way. Knowing several other standard proportional relationships will also help you judge the placement of the ears, the width of the mouth, and the distance between the eyes, for instance, because those averages help you determine the specific proportions of your subject.

“Some portrait artists find it helpful to draw straight or angular lines rather than curving lines because those can sometimes be easier to use when judging distances,” Caporale added. “That is, lines indicating the top, bottom, and side of the head can be useful when determining the placement of the head on the canvas, and straight lines drawn from the head to the edges of the shoulders can aid in accurately putting a neck and chest below the head. You can use whatever system helps you arrive at an accurate drawing, but the most important thing is to be confident that you have the right framework on which to build your oil portrait.”

Caporale’s drawing demonstrations are usually done on a 16″-x-20″ sheet of paper because she finds it to be the most comfortable size for head-and-shoulders portrait paintings of children. A student in the workshop asked Caporale to clarify a remark she made about using a plumb line to evaluate the lines of a drawing. She responded by explaining that portrait artists use a variety of tools, including weighted strings, rulers, pencils, and paintbrushes, held in front of their eyes to judge the lines of their drawings against horizontal or vertical lines. “The point is to determine if your drawing is slanting one way or another and whether you have the features properly aligned,” she said. “You can use an actual carpenter’s plumb or just hold a pencil in front of your eyes at a 90-degree or 180-degree angle to your line of vision to make those determinations.”From an article by Stephen Doherty.

Think Exaggeration in Your Portraiture–But Maybe Don’t Paint That Way

Sita and Sarita by Cecilia Beaux, 1893, oil painting, 37 x 25Sita and Sarita by Cecilia Beaux, 1893, oil painting, 37 x 25.

I’ll be the first to argue that caricature and portraiture are completely different types of art, but both use many of the same strategies that can make fine art portrait painting and portrait drawings memorable.

At its most essential, a caricature is an exaggeration or distortion of a person’s physical characteristics, but it is still a study of a person’s physicality. We’ve all seen the boardwalk artists at the beach who draw quick caricature sketches in a handful of minutes. The artist gets the shape of the face and accentuates two or three physical features of the sitter and voila, a caricature.

Although fine art portraiture takes longer to create, an oil portrait painter still uses the same approach. First, it is essential to get the shape of the head right. This is a crucial step because it determines how the head sits on the neck and leads into the torso, and how the features sit on the face. Think of how you are able to recognize a friend or acquaintance from across the street. The same rule applies for a portrait; the sitter will be recognized first from their big ol’ noggin.

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With a caricature, the artist will usually exaggerate a person’s features-eyes, lips, chin, ears, or hair, even freckles or big eyelashes. It always varies, but usually the artist doesn’t emphasize everything and only select one or two features for the biggest impact. Fine art portrait artists should work in the same way. Not in terms of exaggerating the size or proportion of a person’s features, but drawing attention to certain aspects of a person with color, light and shadow, and brushstrokes.

Looking at a model and first thinking of how you’d draw their caricature can really open up ypur mind to what you could showcase in their portrait. And, just like caricatures, a portrait that visually “heightens” certain aspects of a person’s looks will certainly stand out from the crowd. From an article by Courtney Jordan.

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Courtney Jordan

About Courtney Jordan

  Courtney is the editor of Artist Daily. For her, art is one of life’s essentials and a career mainstay. She’s pursued academic studies of the Old Masters of Spain and Italy as well as museum curatorial experience, writing and reporting on arts and culture as a magazine staffer, and acquiring and editing architecture and cultural history books. She hopes to recommit herself to more studio time, too, working in mixed media.