Painting a portrait, step by step process and useful tips!

Painting a portrait requires similar skills and methods than any other figurative subjects. However, the artist needs to be more attentive to drawing details and colors nuances. I have done commissioned portraiture for many years and along the way, have developed techniques that have worked well for me and for my students. Here are the steps and tips that will help you paint a good portrait with a faithful likeness.

1. Choosing (or taking) the right photo

This is probably the most important step that is unfortunately often neglected. I highly recommend taking our own photos but when this is not possible, you need to choose the right picture. To create a good illusion of form, the photograph needs at a minimum:

A single light source (or a significantly dominant light source)
No overexposure or underexposure
Good range of values from near a white highlight to near black shadows with colorful mid-tones (more on that later)
Absolutely no flash photography, it flattens the form and kills the beautiful form shadows.

Try choosing a subject that is in direct light and avoid strange cast shadows on the face such as leaves from a tree. It is preferable to have some form shadows as it helps to create a convincing three-dimensional illusion. One of the classical ways to light a face is the use of the “Rembrandt light” which lights the subject from a 45-degree angle, sideways and above. I used such a lighting, though with a stronger light than a typical Rembrandt for my portrait of Annie:

2. Drawing your subject

If you are not comfortable sketching your subject, use the grid method to make sure you don’t have major proportions errors.

Things to check:

Imagine a straight vertical line going from the pupils to the mouth. Often this line will meet the corner of the mouth. If not, take note of where the mouth ends compared to that line.
Imagine a straight vertical line going from the inside corner of the eye to the nose, often this line will meet the side of the nose. If not, take note of where the nose lines up.
Measure the distance between the pupils, then turn your measuring instrument (often your pencil) vertically to check the distance between the pupil and the mouth. Often this distance will be the same.
Measure the height from the eyebrows to the hairline and compare that measure to the eyebrows down to the base of the nose. Use the same measure to compare the distance from the bottom of the nose to the bottom of the chin. Often these three measures will be the same, if not take note of the difference.

There are many ways to check measurements of the face. The measures above will help avoid most major problems. One easy way for beginners is to use the eye-width method where one eye width is used vertically and horizontally to measure the features and proportions of the head. All these measurements work well mostly with a front-facing portrait. As soon as the view moves to an angle, things will line up differently so you have to observe carefully how the features align.

The perspective of the head

When viewed from an angle, the head should be viewed as a block with perspective lines. The eye most away from the viewer will have appeared smaller than the other eye.

3. Preparing your palette

A well-organized palette will not only make your painting progress faster but you will be able to control your values and create good forms. Your palette should be organized in parallel columns of values from light to dark. At a minimum, you should have a column of warm skin tones, a column of neutral skin tones and a column of cool skin tones. Here is an example of a well-organized palette, courtesy of Rita Romero. Since skin does not have vivid colors, you will have an easier time using broken colors in the Ochre, Sienna and Umber families. A middle red, such as a Cadmium will be useful to create deep darks when mixed with black and pink accents when mixed with white.

My go-to colors for portraiture are: Titanium white, Yellow Ochre Light, Burnt Sienna (or Transparent Oxide Red), Cadmium Red (or Winsor & Newton Bright Red), Ultramarine Blue, Raw Umber and Ivory Black. This palette will also work for virtually all subjects except some rare exceptions like some flower colors or jewelry.

4. Start with the darkest dark notes

Since all values work in relation with one another, I generally advise my student to start with their darkest dark. These dark notes will work as a reference for your shadow values which in turn serve as a reference for the light values. Where to look for the darkest notes on a painted portrait:

The pupils
Cast shadows under the upper eyelids
Cast shadows in the fold of some clothing
Cast shadows in the hair

5. Lay down your large dark shapes

By concentration only with the darks in this stage, you can sketch your subject with large masses. Some of my students find it easier to use masses instead than lines to sketch their subject, This is something that I encourage everyone to at least experiment with. The portrait below was started with a mass monochrome sketch.

6. Painting the shadows

It is important to keep the shadow color family distinct from the light color family. The main reason for this is that the colors in the lights will behave according to the nature of the light. For example, a cool light will shift all colors in the light toward the blue-green end of the spectrum. Also, a cool light will often have an opposite effect in the shadows and shift the shadow colors toward the warm end of the spectrum. Inversely, a warm light, such as the sun or an incandescent light will tend to create cooler shadows with a hint of purple.

One of the reasons to start with the shadows is that it is easier. Shadows tend to be flatter and don’t require the same level of work than mid-tones. Also, with the darkest dark notes in place, you can more easily stay a little higher (lighter) on the value scale. In other words, you don’t risk going too dark, since you need to keep a value difference with the darkest dark.

7. Painting skin tones in the light

A. Mid-tones

Mid-tones are the areas that receive the light but do not include the highlights. This is where most of the modeling of the face happens and where we have to be the most attentive to the exact colors. One way to get a convincing skin tone is to identify where the colors switch from warm to neutral and from neutral to cool. It is this dance of warm-neutral-cool colors that makes a skin colors feel real.

Look at your arm and try to spot those cooler-warmer-greyer tones! Exact colors are secondary to this warm-cool-neutral relationships. Generally speaking, areas around the nose, eyes, ears, and cheeks will be warmer. Forehead and chin will tend to be cooler. Most receding planes tend to be more neutral. Of course, these are very general rules and vary according to the light and environment colors bouncing on the subject. Nothing beats careful observation to identify these mid-tones.

B. Highlight

The highlights are those small areas that receive direct light. These can be found in three places, all facing the light source:

On planes like the top of the cheeks
On points on all spherical shapes such as the tip of the nose or the chin
On cylindrical shapes such as the bridge of the nose, arms, fingers.

The color on these highlights will tend to be attenuated due to the strong light. Often you will notice a shift toward a much cooler white. One useful tip that I can give you is to mix your lightest skin color with white and a little green to get that bright highlight that will pop and make the form advance.

When painting a portrait from a photo, often the brightest area on the photograph can be overexposed. Be careful to avoid laying paint on large area with a single value. Since the head has no flat surfaces, the values have to be continually changing and the highlights should be very small.

8. Painting the area between the light and the shadow

This area is where the magic happens. DO NOT mix your shadow color with your light color to paint this turning edge! This area, although small, is distinct. It is often where you will find the most colorful notes and the reason is simple. The light washes out the color in the light area and the shadows often have too little light to transmit the colors well. This leaves the turning edge with just the right amount of light to show the beauty of the color, which can be surprisingly vivid. If you look at my portrait of Krysten above and below, you can see the bright red on the turning edge. Similarly, my painting of Annie at the top has a strong color and temperature switch on that edge (red-green).

9. Painting the Background

Portraits are demanding, errors in drawing are unforgiving and the attention to details require great concentration and time. When doing commission work, often we don’t have a choice for the background but when we do, it’s time to loosen up and be as creative as we want!

There are still a few guidelines for painting the background:

Respect the nature of the light on the sitter. Check for the direction and the temperature of the light.
Try to integrate the sitter by using some of the skin, hair and clothing color on the background.
Don’t steal the show. Make the background interesting but don’t forget your focal point has to dominate.

10. Painting the final touches

I have often heard that it takes two people to do a painting, an artist who does the work and someone else to tell her/him when to stop. If you don’t have this someone else, here are a few things to check before you sign pour painted portrait:

Check the lightest light, can it be even lighter?
Check your darkest dark, can it be darker?
Check your edges, do they need some softening of hardening?
Check your transitions between light and shadow, did you nail the color and intensity?
Look at your painting upside down and sideways, is there something that doesn’t work?
Look at your painting through your phone, does it work when viewed as small as a thumbnail?

If everything checks out, time to sign and to take a good picture!

Please let me know if you found these tips useful. The last advice I will give is to find a good portrait artist to guide you along your learning journey. This is how most artists have learned for centuries and it is still the best way today.

If you are interested in commissioning a portrait, you can get more information here.

All portraits in this article are by the author.