Where to Start When Painting a Portrait: A Simple Step-by-Step Guide

Painting a portrait feels intimidating. You stare at the face-eyes, nose, lips-and wonder where to even begin. You’ve seen masterpieces, watched YouTube tutorials, and now you’re holding a brush, paralyzed by the fear of messing up someone’s likeness. But here’s the truth: portrait painting doesn’t start with perfection. It starts with observation, structure, and patience.

Start with the Shape, Not the Details

Most beginners jump straight to drawing eyes or shading cheeks. That’s like trying to build a house by putting in the windows first. You need the frame before the wallpaper.

Begin by blocking in the overall shape of the head. Use a soft pencil or thin brush to sketch a simple oval. Then add a vertical centerline and a horizontal line for the eyes. These aren’t measurements you need to be exact about-they’re guides. The eyes sit roughly halfway down the head. The bottom of the nose is about halfway between the eyes and the chin. The mouth is a third of the way from the nose to the chin.

This isn’t about copying a photo. It’s about understanding proportions. Even if you’re painting from life, use these rules as your anchor. They’ll keep you from making the head too long, the eyes too high, or the chin too sharp.

Use a Limited Palette to Avoid Overwhelm

You don’t need every shade of red, brown, and yellow to paint a convincing portrait. Start with five colors: titanium white, cadmium red, yellow ochre, burnt sienna, and ultramarine blue. That’s it.

Mix these to create skin tones. Add a touch of blue to warm tones to cool them down. Add a hint of red to make cheeks flush. Burnt sienna gives you earthy shadows. Yellow ochre warms the highlights. White isn’t just for brightness-it’s for softening edges and creating transitions.

Painting with a limited palette forces you to focus on value (light and dark) instead of color. And value is what makes a portrait look real. A perfectly colored face with wrong values will look flat. A simple gray-scale portrait with correct values will look alive.

Paint from Dark to Light

One of the biggest mistakes beginners make is painting the whole face in one go-light, midtone, shadow-all at once. That leads to muddy colors and lost forms.

Instead, start with the darkest areas. Block in the shadows under the jawline, the eye sockets, the sides of the nose. Use a thin brush and a mix of ultramarine blue and burnt sienna. Let it dry.

Then move to the midtones. These are the skin tones you see in the flat areas of the face. Don’t blend too much yet. Keep your brushstrokes intentional.

Finally, add the lightest areas-highlights on the forehead, cheekbones, tip of the nose. Use mostly white with a whisper of yellow ochre. This approach builds depth naturally. Each layer informs the next.

Focus on the Eyes Last

The eyes are where people expect to see life. But they’re also the hardest part to get right. If you paint them too early, you’ll fixate on them and lose the rest of the portrait.

Paint the eye socket first-a dark, recessed shape. Then the iris. Don’t make it a perfect circle. Real irises have variations in color and texture. Add a tiny white dot for the catchlight, but don’t overdo it. One or two dots are enough.

The eyelids matter more than you think. The upper lid casts a soft shadow over the eyeball. The lower lid is rarely flat-it curves slightly. Pay attention to how the eyelashes grow in clusters, not as individual lines.

Don’t rush the eyes. Wait until the rest of the face is 80% done. Then come back. You’ll see them with fresh eyes.

Paint the Background Before the Face

Most people paint the background last, thinking it’s just filler. But the background sets the tone. A dark background makes the face pop. A light background creates a soft, airy feel. A colored background can influence the skin tone.

Paint the background first, using a large brush. Let it dry completely. Then paint the face over it. This gives you a clean edge and helps you judge the value of the skin. If the background is dark, you’ll know your highlights need to be brighter. If it’s warm, you’ll adjust your shadows accordingly.

This trick is used by old masters like Rembrandt. It’s not about being lazy-it’s about controlling contrast from the start.

Step Back Often

You’ll spend hours hunched over your canvas, tweaking a single eyebrow. But your eyes get used to what’s there. You stop seeing mistakes.

Step back every 15 minutes. Walk across the room. Look at your portrait from five feet away. Squint. What do you see? If the face looks like a blob, your values are off. If the nose looks crooked, your proportions are off.

Use a mirror. Hold it up to your painting. The reversed image tricks your brain into seeing flaws you missed.

Accept Imperfection

No portrait is ever perfect. Even the greatest artists left subtle quirks-the slight tilt of a head, the uneven smile, the shadow that doesn’t quite match. That’s what makes it human.

Your first portrait won’t look like a photograph. And that’s okay. It should look like a painting. It should show your hand, your choices, your feeling.

Painting portraits is about connection. Not replication. You’re not trying to copy a face. You’re trying to capture a presence.

Practice with Short Sessions

Don’t try to finish a portrait in one day. Set a timer for 45 minutes. Paint just the eyes and nose. Then stop. Come back tomorrow. Do the mouth and jaw. Then the hair. Then the background.

Short, focused sessions build confidence. You learn what works without burning out. You start to recognize patterns-how light falls on a cheek, how shadows gather under the chin.

Keep a sketchbook. Doodle faces from photos, magazines, people on the train. Don’t aim for finished work. Just observe. The more you look, the more your hand learns.

What to Avoid

• Don’t use black for shadows. It flattens the face. Use dark blues, purples, or browns instead.
• Don’t blend everything with your brush. Let some edges be sharp. Others soft. Real skin doesn’t have smooth gradients everywhere.
• Don’t paint the whole face in one color. Skin has warmth, coolness, redness, yellowness-all in the same spot.
• Don’t copy photos exactly. Photos flatten depth. Your job is to restore it.

Portrait painting isn’t about talent. It’s about attention. The more you look, the more you see. The more you see, the more you can paint.

Start small. Start simple. Start now. Your first portrait won’t be perfect-but it will be yours. And that’s where the real art begins.