Portrait Drawing Pointers

Updated: Sep 4, 2020

Strategies for drawing portraits, that I learned by reading The Mad Art of Caricature.

In my last blog post, I talked about how challenging it can be to draw portraits. Some unexpected help came along, when a friend recommended that I pick up a copy of The Mad Art of Caricature by Mad Magazine cartoonist Tom Richmond. It may sound a little unusual to read up about caricature techniques if you don’t draw caricatures. Don't be fooled!


This book is jam packed with lessons for portrait drawing no matter what your artistic style.


With the help of one of my favorite television characters, Mary Tyler Moore, I’ll share a few pointers that have been massively helpful to me. Here is just some of what you'll learn by reading The Mad Art of Caricature.



1) Picture the eyes and nose as a T shape.

Start by simplifying the eyes and nose, so that they form the letter T. This will help you map the face and avoid being tripped up by details. A good way to envision the letter T is to blur your vision so you see only the basics shapes of the subject’s face.


Pay attention to the relationship of the features. Ask yourself questions like “Is the stem (nose) long or short?” and “Is the top of the letter (eyes) close together or far apart? Tall or short?”.


Sometimes a person’s eyes curve up or down slightly, creating more of a Y shape (if the outside corners point up) or arrow shape (if the outside corners point down).

The relationship between the eyes and nose can vary quite a bit from person to person.


Practice observing these differences in your day to day life. You can observe faces while you watch T.V. or even stealthily while you’re in a zoom meeting. I don’t recommend staring during one on one conversations though. The grocery store clerk has enough on their mind without wondering why this random customer won’t stop making eye contact.

Mary Tyler Moore illustration with blue oval overlay.

2) Keep the face shape simple.

You may have heard that a person’s face shape is a large part of what makes them recognizable. That’s true! Its tempting to try and capture every curve, crevice, and shadow of the subject’s face shape before you even get started on the rest of the features.

Resist this urge. While face shape is incredibly important, try not to complicate it. Observe the person’s face and ask yourself what shape it reminds you of. An oval? A circle? A rounded rectangle? A pear? Start by drawing this rudimentary shape. There will be time later to fill in the nuanced details like the hairline, cheekbones, and chin.

If you’re struggling to figure out what shape to use, ask yourself questions like “Is their face long or short? Narrow or wide? Does their chin come to a sharp point? Does their forehead get wider or narrower towards the top?” Using language can help you process what you’re looking at.

Note: Many instructions on how to draw faces will tell you to start by drawing an oval, then map out the features next. Personally, I find it easier to start with the eye/nose T shape that we talked about in tip #1, then draw the face shape around it. I suggest trying both ways to see which technique is more successful for you.



Mary Tyler Moore Illustration with triangle overlay.
An triangle shows classic proportions.

3) Ask yourself questions to understand the face shapes.

I’ve given some examples of questions you can ask yourself while you are drawing. With so many details that make up a face, using language can help you break it down into simple forms. You can think of these like questions on a multiple choice test. For example you could ask:


The bride of the nose is:

a. narrow

b. wide


The tip of the nose turns:

a. up

b. down

c. neither (straight)


Keep asking questions! I don't know the science of why this works exactly. I suspect it has something to do with the fact that humans are constantly communicating through language. Try it and see if your drawings improve. If anyone thinks its weird that you’re talking to yourself, maybe just point to your headphones and gesture like you’re on an important phone call.

Mary Tyler Moore illustration with eye outlined.

4) Focus on the part of the eye that is visible. Imagine for a moment you are drawing just the eyes themselves. Ignore all the window dressing that surrounds the eyes like the, the lids, lashes, wrinkles, and makeup. Draw that shape accurately first, and all the other details second.


One technique to help you observe the shape of the eye is to draw an imaginary line from the outer corner of their eye to the inner corner. Observe how much of their eye falls above or below this equator line.


Mary Tyler Moore Illustration with line across eyes.

Here you can see Mary’s eyes fall more above the equator line. Notice how most people have most drastic curve on top of eye, and lower half is a more gentle curve. This imaginary line can also help you observe whether or not the subject’s eyes are angled upward, downward, or straight across.



5) Notice the negative space around the mouth. Mary Tyler Moore can famously “turn the world on with a smile”. So its pretty important that my drawing do her smile justice. One tip for placing the mouth is to look at the negative space above and below the mouth. This will help you find where the mouth naturally falls between the nose and the chin.


And while we’re talking about smiles… drawing teeth takes practice! Try not to get carried away drawing each individual tooth. There is a fine line between drawing a welcoming smile and drawing a terrifying grill of menacing teeth. Here are a few things to keep in mind when drawing teeth:

  • Teeth recede back into the mouth. When a person smiles, their teeth at the front will be more prominent. Towards the corners of their smile, their teeth will be shadowy. Add gradual shading to those teeth.

  • Represent teeth with minimal, broken lines. Drawing a clean outline around every tooth will bring too much attention and emphasis to them. Use as little line as you can to represent the teeth, adding little by little as you go.

Don't Take My Word for It. Read the book.


These are just a few of the pointers I learned from reading The Mad Art of Caricature. The author, Tom Richmond, goes in depth and provides hundreds of visual examples. By practicing the techniques in the book, I’m seeing a huge improvement in my portrait skills. In the words of LeVar Burton "Don't take my word for it." Check out the book at your local library or buy a copy online.

Have any good portrait drawing tips? Share them in the comments below!

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