Chasing a Face: How I catch a true likeness

I love doing demos at my weekly portrait class and we sometimes tackle well known faces. I often get asked by my students how I get a true likeness in my portraits. It's all well and good drawing a convincing head but getting it to look like the subject is a whole new set of challenges.

For me it's about getting the specific relationships between the features. Small inaccuracies matter a lot more than people expect. Here’s how I typically approach it:

Miriam Margoles - Pastel on Canson paper

1. Start with structure, not details

Before drawing eyes or lips, map the head as a 3D form. Think in terms of the structure- skull, jaw, eye sockets and planes of the face. I resist the urge to draw details like nostrils, eyelashes, wrinkles until the very end.

2. It's all about proportions and relationships

Instead of drawing an “eye,” draw this person’s eye in relation to their nose, brow, and cheek. Measure distances:

• How wide is the nose compared to the space between the eyes?

• Where do the corners of the mouth align vertically?

• How far is the chin from the lower lip compared to the nose-to-lip distance?

  These comparisons is where the likeness is.

  
  

  

  Zelenskyy - Pastel on Canson paper

3. Train your eye with comparative measuring

Use your pencil to check angles and lengths. Artists like John Singer Sargent were known for obsessively comparing angles rather than relying on assumptions about anatomy.

4. Get the big shapes right first

Block in shadow masses before refining features. A good way to simplify values is to squint at your subject — this helps you see the face as a pattern of light and dark rather than a collection of parts.

Scene from the film Hamnet - Pastel on Canson paper

5. Prioritise Negative space

This was a game changer for me. If you're having trouble drawing an eye, draw the shapes of space around the eye. The brain can't label these abstract shapes of flesh surrounding the features, therefore observing them more accurately

Owen Cooper, Adolescence - Pastel on Canson paper

6. Think in an Abstract way

See the face as a series of abstract shapes and forms. Rather than identifying each feature, break it down into shapes to stop your preconceptions jumping in.

'Yungblud' - pastel on Canson paper

7. Work from general → specific

Avoid finishing one eye before placing the rest of the face. Develop everything gradually so proportions stay consistent.

8. Step back often

Look at your work from a distance or flip it up side down. Mistakes in likeness become obvious when you break familiarity.

Stephen from 'Traitors' series - Pastel on Canson paper

9. Capture expression, not just anatomy

A technically accurate face can still feel “off” if the expression is wrong. Pay attention to how features shift with emotion—slight changes in eyebrows or mouth corners can transform likeness.

10. Practice from life and photos

Working from life trains perception; photos let you slow down and analyse. Combining both builds accuracy faster.

Diane Morgan- Pastel on Canson paper

Truth is, the art of portraiture is a constant battle, wrestling for the likeness, losing it and then pulling it back again. That’s part of the process. It isn’t a formula you solve once—it’s a sensitivity you develop over time.

Most of the time my portraits feel hard-won. Not effortless, not perfect—but alive in a way that only comes from having nearly lost them.