Painting Portraits: Capturing More Than a Likeness

Over the winter, I was lucky enough to spend some time in the British Virgin Islands, visiting my family. As well as enjoying the sunshine and slower pace of life, I took the chance to do something I don’t often get the time to do properly at home — sit and paint portraits just for the joy of it.

I worked in watercolour, painting a couple of portrait studies of my grandchildren from life and from photos taken while I was there. There’s something really special about painting people you love. You’re not just trying to get the features right — you’re trying to capture a feeling, a moment, a little glimpse of their personality.

Watercolour felt like the perfect medium for this trip. It’s light to travel with, quick to set up, and has a lovely softness that suits portraits beautifully. 

Portrait painting can feel intimidating, especially if you’re used to landscapes or still life. But it doesn’t have to be. Like anything in art, it’s a skill you build up over time, and every portrait you paint teaches you something new.

Five Top Tips for Painting Portraits

Here are a few practical tips that I always come back to when I’m working on portraits:

1. Get the Structure Right First

Before you even think about details, spend time on the basic head shape and the placement of the features. If the proportions are off, even beautifully painted eyes won’t save the likeness. Light pencil guidelines can really help here.

2. Think in Shapes, Not Features

Try not to “draw an eye” or “paint a nose.” Instead, look for the abstract shapes made by light and shadow. Faces become much easier when you stop naming things and start seeing shapes and tones.

3. Don’t Overwork the Eyes

Eyes are the focus of a portrait, but over-detailing them too early can make a face look stiff. Suggest more than you define at first, and let the portrait grow naturally before refining small details.

4. Watch Your Values

Good portraits are built on strong light and dark relationships. Squint at your reference and simplify the tones. If the values are right, the likeness will often fall into place even without lots of detail.

5. Leave Some Edges Soft

Not every edge needs to be sharp. Softer edges around hair, cheeks, and in shadow areas help portraits feel more natural and painterly — especially in watercolour, where softness is part of the magic.

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Portraits as Stories

What I love most about painting portraits is that they become little records of time. My grandchildren will grow and change so quickly, and these small watercolours will always remind me of that particular winter in the Caribbean — the light, the warmth, the quiet moments sitting and painting while the world carried on around us.

Portrait painting isn’t just about accuracy. It’s about connection. Whether you’re painting family, friends, or working from photos, you’re learning to really look at another human being — and that’s a powerful thing.

Coming Soon: An Online Portrait Course

I’ve had quite a few people ask about learning portrait painting, and it’s something I’ll be working on over the coming months. I’m currently developing an online portrait course that will guide you step by step through the process — from drawing the head structure, to painting convincing features, to capturing likeness and character.

If portrait painting is something you’ve always wanted to try (or return to), keep an eye on the website — I’ll be sharing more details soon.

In the meantime, I hope these little watercolour portraits from the BVI inspire you to pick up your paints and have a go yourself.

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