Drawing the Head for Artists: Techniques for Mastering Expressive Portraiture

Drawing the Head for Artists: Techniques for Mastering Expressive Portraiture

by Oliver Sin


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Drawing the Head for Artists is the definitive modern guide to drawing the human head and portrait, featuring the classic mediums and methods of the Old Masters.

Written by celebrated portrait artist and veteran studio instructor Oliver Sin, this richly informative and beautifully illustrated volume leads readers step-by-step through his method, from establishing a point of view to applying the timeless principles for creating an accurate and expressive likeness.

Among the topics covered:

  • Essential Materials & Techniques:Learn about necessary supplies and basic drawing techniques, including hatching, various stroke styles, and blending.
  • Applying the Essentials: Explore how the concepts of sight-sizing, value, negative space/shapes, and plane changes factor into a portrait’s underlying structure.
  • Techniques for Creating Depth & Dimension:Investigate how contrasting shapes, overlapping forms, and linear and atmospheric perspective are used to enhance depth.
  • Creating the Illusion of Three Dimensions: Examine how edges—contours as well as changes in value—are used to convey three-dimensional form.
Brimming with striking images that document all the phases and details of the author’s process, Drawing the Head for Artists inspires and informs all artists, from aspiring to accomplished, on how to successfully portray the physical subtleties and emotional eloquence of the human face.

Product Details

ISBN-13: 9781631596926
Publisher: Quarry Books
Publication date: 08/06/2019
Pages: 160
Sales rank: 238,527
Product dimensions: 8.40(w) x 10.90(h) x 0.60(d)

About the Author

Oliver Sin graduated from the Academy of Art University in San Francisco with a Bachelor of Fine Arts in Illustration. He began his career as a computer games concept artist, including stints at LucasArts and 3DO, and has been teaching for the Academy’s School of 2D Animation and the School of Fine Art since 2001. His award-winning portrait art has been recognized by the Portrait Society of America, and featured on ArtistsNetwork.com, in the journal  The Art of the Portrait, and in International Artist and  Southwest Art magazines. Born in Hong Kong, Sin has lived in San Francisco since 1990.

Read an Excerpt




Vine Charcoal and Willow Charcoal

I use vine and willow charcoal sticks for my portrait drawings to achieve the chiaroscuro technique. Chiaroscuro, an Italian term meaning light (chiaro) and dark (oscuro), is used to enhance the dimensionality of drawings by creating smooth, subtle transitions among values.

Artists use vine and willow charcoal, which are made by burning vines or branches in a kiln, for their versatile properties. Sticks of vine and willow charcoal, which are fragile and break easily, are available in a variety of lengths, thicknesses, and densities or degrees of hardness. These mediums produce marks in a wide range of values, from very light to intensely dark, which suits them perfectly to the chiaroscuro technique.

Willow charcoal is black, while vine charcoal is dark gray. Vine charcoal's lighter tone and ease of removal make it a favorite of artists for creating initial sketches or preliminary compositions, but it is less suitable for creating detailed artworks because it has a tendency to fade. Darker values can be achieved by applying willow charcoal over vine charcoal, or applying the two together. Vine charcoal can also be combined with other charcoal mediums, such as com- pressed charcoal.

Kneaded Eraser

When working with vine and willow charcoal, I use a kneaded eraser to remove, lift, and redistribute values.

Because kneaded erasers can be easily stretched and shaped, they're excellent for subtractive work, to shape form, refine line- work, and create highlights.

Other helpful tools for subtracting and manipulating values are retractable erasers, gum erasers, extra-soft erasers, single-edged razor blades, and bristle brushes. The narrow head of a retractable eraser allows for greater control in adjusting details.


Unfixed charcoal drawings are extremely vulnerable to surface damage. The slightest movement or an accidental touch can leave a noticeable smudge, reduce the intensity of value, and muddy highlights. Fixative can actually strengthen a drawing, allowing for additional layering by acting as a "glue" for a new application of medium, and ensuring that fine dustings are not lost.

Use a workable fixative while a drawing is in process. Note that fixative will change the appearance of a charcoal drawing by darkening its values slightly, and that a heavy coat of fixative will cause charcoal particles to float into the saturated paper's grain, thus compromising the drawing's finer details.

The number of layers of workable fixative you use will depend on the number of layers of charcoal in a drawing. Typically three to five layers of fixative are sufficient.

To finish a charcoal drawing, use a final fixative in a matte sheen.

Compressed Charcoal

Compressed charcoal, which is harder than both vine and willow charcoal, is sold as sticks and pencils. I use this tool sparingly, and usually only to finish a drawing, to help create visual emphasis by defining hard edges (see page 96).


Paper is as important to your artwork as the charcoal you make your marks with. Good paper can make or break a drawing; it can also make the drawing process easier or more difficult.

The paper I use and recommend is Strathmore 400 Series Drawing (18 x 24 inches/46 x 61 cm), which has a durable surface with a medium tooth; and 500 Series Drawing, Medium Surface (23 x 29 inches/ 58 x 74 cm), which is professional grade.

Another aspect to consider is whether a paper is of archival quality, which can also affect its durability as well as the value of the finished artwork.

With the exception of the textured and toned papers I use in two alternate techniques (see page 131), in my experience papers made specifically for charcoal are too textured, and Bristol papers are too smooth, flawless, and nonabsorbent. Regardless, I strongly recommend that you experiment with different surfaces to explore a range of results.


Sketchbooks are great tools for collecting information, forming creative ideas, and keeping a creative journal of exploration. I use sketchbooks predominately for drawing from life. The purpose of a sketch is to observe and capture interesting details and the general pose and gesture of the subject. The more you can observe and appreciate at a glance, the faster you can draw and the more you can capture.

A sketchbook is an avenue for free-flowing creativity. There are no deadlines to meet, no rules, and no client expectations. You can sketch anything or anyone who interests you. Don't worry about finishing any one drawing or perfecting a sketch. The goal of sketching is observation. It's okay to make mistakes. Try to simply have fun, and let your sketchbook become a small passion project.

Sketchbooks are available in a variety of sizes and paper types. I always carry a small, 5-x 8-inch (12.5 x 20 cm) Moleskine sketchbook so I can record anything that appeals to me.

You can sketch with any drawing medium, including pen. Although the permanence of the lines may be intimidating, it motivates artists to observe more carefully before sketching, making it a great learning tool. Try different tools and combinations. With experimentation, you will discover what you prefer.

Sketching is an "anytime, anywhere" pursuit for me, especially when traveling. You may find time to draw while waiting in line, riding public transportation, or sitting in a café, at the airport, or on an airplane.


The possibilities for using drawing materials are limitless, but there are some traditional methods of application you should know


Hatching is the application of tone, or shading, by drawing closely spaced parallel lines. The closer the lines are together, the darker the shading appears. Artists adjust the length, angle, closeness, and quality of the lines to create variation.


Crosshatching is the application of single hatch marks at an angle to existing hatch marks to darken the tone. Hatching and crosshatching are often used together to add dimension and shading.

Side Strokes

Artists draw side strokes (or broad strokes) by using the side of vine or willow charcoal to achieve a wide mark. The appearance varies, depending on the surface texture of the paper.


The blending technique is used to soften lines and gently intermingle values to create a gradual transition among them.

You may use your finger, a cotton swab, or an old rag as tools for blending. You may also use a blending stump, also called a tortillon, which is a long stick of tightly twisted paper. The big advantage to using a stump is its fine tip, which allows for precise control when blending even the smallest details.

Blending can destroy the integrity of a drawing, so it's important to avoid overusing it. This skill doesn't come naturally to many artists, so you'll want to hone it. Be patient and practice until you're comfortable with various blending tools and methods.



Line Shape Form Value Space/Depth Texture Color


It's been said that a line is a moving dot, or a point in motion. Line can guide a viewer's eye by defining edges and outlining shapes. Lines used to outline a shape are called contours or contour lines.

Artists can create the illusion of form in a drawing by varying a line's quality, or thickness. (See also "Using Edges to Convey Form," on page 96.)

Line can also be used to indicate shadow. Shadow areas have thicker contour lines, while lighter areas have thinner ones.

The five types of line, simply defined:

Vertical lines are positioned vertically, or up and down, on the picture plane, without slanting.

Horizontal lines are parallel to the horizon.

Diagonal lines are slanted relative to the picture plane.

Zigzag lines are made from a combination of diagonal lines.

Curved lines gradually change direction.


Shapes play an important role in the creation of art. A shape is a closed contour, created when a line is enclosed, or when a line's ends meet. All shapes are two-dimensional, meaning that they have both length and width.

There are two types of shapes: geometric and organic.

Geometric shapes, which can be described using mathematical formulas, include circles, triangles, squares, trapezoids, pentagons, pentagrams, hexagons, and octagons.

Organic shapes are those irregular, uneven shapes that seem to follow no rules. These expressive shapes are typically not man-made.


The world we live in is made up almost entirely of forms. Form and shape are related. I like to think of forms as three-dimensional shapes. In art, the term form refers to an object that has three dimensions-that is, it has length, width, and height.

I encourage my students to develop their understanding of form, and how to create the illusion of form in drawings, by studying the effect of light on objects.


Value refers to the lightness or darkness of a color or tone. Value is incredibly important in a drawing because light and dark values describe the form of an object. All objects have light, middle, and dark values when exposed to light.

Value relates directly to light-we see things because of light on objects, or illumination. Light reflects off the object into our eyes and our mind processes that light and rationalizes what we see. Value is the key to the illusion of light, and a good realistic drawing depends on a range of values. The effects of light on form are described in the diagram below.

When drawing portraits, light and shadow translate from simple planes and shapes into detailed variation of value and line.


In art and design, space generally refers to the sense of depth in a work of art. When drawing on a two-dimensional surface (paper), the artist creates the illusion of space to give the sense of three-dimensionality. (See also "Atmospheric Perspective," page 98.) Space can also refer to the use of positive and negative space in a work of art. Positive space refers to the object or subject, while negative space refers to the empty areas around and within the subject.


Texture is an important aspect any work of art, especially portraiture. In two-dimensional artwork, texture can be implied or real. For example, you can achieve the appearance of smooth, delicate skin in a portrait drawn on smooth drawing paper far more easily than on rough drawing paper. Texture can also be implied with drawing techniques such as hatching, crosshatching, and scribbling.


Color can be defined by three properties: hue, value, and intensity. Hue refers to the actual name of a color (e.g., blue). Value refers to that hue's lightness or darkness. Intensity refers to the vividness, or quality, of the hue.

Although the principal technique I explore in this book applies black drawing mediums in varying values to white paper, I also discuss an alternative technique that uses black and white mediums on toned or colored paper (see page 138).




Artists use a standard set of measurements to create accurate proportions when constructing a head drawing. The following serve as general guidelines. All faces are different, and individuals have varying proportions. Use these guidelines as a starting point, but stay true to the actual proportions of your subject.

The general proportions of the head can be divided into thirds:

One-third from the hairline to the eyebrows One-third from the eyebrows to the nose

One-third from the nose to the chin


It's important to remember that achieving a likeness is predicated on the artist first depicting the three-dimensional structure of the head, which is often described as the planes of the head.

The shape of the head consists of six planes: top, bottom, front, back, and two sides. Both the front and side planes of the head recede from the viewer's eyes in a three-quarter position, as shown here. The features on the front and side planes diminish in size as they turn from the viewer, under the rules of perspective.


There are three standard viewpoints the artist may choose from when establishing the pose of a portrait: front, profile, and three-quarter. Each viewpoint affects the shapes, shadows, highlights, and proportions of the head and the facial features.

Front Pose

Drawing the face from the front is generally less interesting than drawing a profile or three-quarter view because it lacks depth and shape. However, it can be effective for a dramatic portrait in which the sitter's face is very expressive.


The nose is an excellent subject to practice the elements of shading and blending and how they apply to all the facial features. The nose is important to the overall size and scale of all the other facial features. If you can draw a nose well, you're on your way to very good portrait drawing!

Never outline the nose; instead, use blended tones to give the illusion of form. In general, the nose is a triangular, wedge-shaped block that is narrow and depressed under the brow and broad and prominent at its base. The nose is composed of soft edges where it gently curves and hard edges where the planes overlap. The tip of the nose is similar to a sphere. A common mistake is to make the nostrils too dark, shaped, and noticeable; instead, treat this area lightly. Drawn inaccurately, the nose affects the total outcome of the portrait and ruins the likeness.


The ear comprises many interlocking shapes. Because it is curved, with rounded surfaces, there are many shadow edges and lots of reflected light and highlights to watch for. The ear projects from the head, so there are also cast shadows. The ear is shell-shaped, and the outer contour looks like a top-heavy letter C, wider at the top and narrower at the base. In the center is a bowl- like depression.

Approach each ear as though you have never drawn one before. The same ear can be a new challenge each time you draw it, because the angle and shadows change with each new pose.


The mouth, much like the nose, must be viewed as shapes and developed with various values and shading to define it. Because the mouth doesn't project from the face as much as the nose does, the cast shadow is not as dark; the darkest dark is in the corner of the mouth, which is called the pit.

The mouth is very important in conveying the mood or feeling of the individual. Though the expression of the eyes may be subtle, the mouth expresses emotion more obviously.


The eyes are often referred to as the "windows to the soul" because they convey so much emotion and personality. This is one of the most important aspects of a good portrait, and I begin all my portraits by rendering the eyes first. In this way, I capture the spirit of the person right away, and I always know early on whether I have missed the personality of the subject in my work.

Profile Pose

In this pose, the head is viewed from one side. A masterful profile portrait is always appealing and can be mysterious. Profiles are a good choice for beginning artists because you only draw one half of the face. With practice, you'll internalize the knowledge and be able to visualize without having to draw all the construction lines.


1 | The shape of the nose in profile is triangular; pay attention to the height and width of the nose, and mark the shape with straight lines.

2 | Shape the bottom plane of the nose and the wing.

3 | Building on your guidelines, define the contours more precisely to form the planes of the nose and the nostril wing. Use just a few strokes to divide the tip of the nose and the nostril into separate shapes. Add the shape of the nose's cast shadow.

4 | Begin to block in tone with broad strokes, using the flat side of the vine charcoal. The light is coming from the top, so the top plane of the nose is in the light, while the side and bottom planes are in shadow.

5 | Strengthen the dark tones to form clear distinctions between light, midtone, and shadow on the side and underside of the nose.


Excerpted from "Drawing The Head for Artists"
by .
Copyright © 2019 Quarto Publishing Group USA Inc..
Excerpted by permission of The Quarto Group.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents

Preface: Creating a Portrait with Spirit, 8,
Key Mediums & Tools, 16,
Sketchbooks, 22,
Basic Drawing Techniques, 26,
The Elements of Art, 30,
Basic Proportions, 44,
Planes of the Head, 45,
Posing the Subject, 46,
Developing a Portrait from Start to Finish, 68,
Drawing Hair & Facial Hair, 74,
Exploring the Use of Light, 80,
Using Edges to Convey Form, 96,
Atmospheric Perspective, 98,
Beyond Basic Poses: Contrapposto of the Head & Neck, 102,
Hats, Scarves & Collars, 108,
Expressing Mood with the Hands, 114,
Drawing Children, 118,
Drawing Elderly People, 124,
Starting with a Creative Background, 132,
Working with Toned Papers, 138,
Resources, 155,
Acknowledgments, 156,
About the Author, 157,
Index, 158,

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Drawing the Head for Artists: Techniques for Mastering Expressive Portraiture 5 out of 5 based on 0 ratings. 4 reviews.
Anonymous 4 months ago
I love this book! The pictures are gorgeous and diverse. The explanations are clear and the author walks through the process in detail beginning with a discussion of tools. I read an ARC copy. Thank you to the publisher and NetGalley! #DrawingTheHeadForArtists
ErikaSarutobi 4 months ago
The artstyle is completely stunning! However, this book is not for beginners. You got to have some basic knowledge on how to draw heads before picking this up but once you do, you won't regret it! This book also teaches you how to draw elderly and children. There are some tutorial on drawing certain facial parts too. If your artstyle is closer to anime-ish, I'm not sure if it'll be very helpful for you since this artstyle is closer to realistic art. But if it is realistic, I definitely will recommend this! The shading is extremely beautiful, I loved every page when I went through it. Thank you Netgalley for providing me with the digital copy for an honest review.
Anonymous 6 months ago
This book is full of both inspiring charcoal portraits and detailed explanations on everything from charcoal, paper, mark making, hard/soft edges, poses, lighting, facial features, hair, colored papers, male vs female profiles, children vs adults vs elderly, etc. There are 11 progression drawings with more than 2 steps each, and several more showing a basic drawing and then a finished drawing with explanations on how the results were achieved. I counted 108 individual portraits, but perhaps it’s safer to just say there are over 100 gorgeous portraits that should inspire and encourage the inner artist in everyone to break out the charcoal and start practicing. This is a book that will be handy to keep accessible as a reference during the journey to becoming a better portrait artist as there is simply too much information and too many tips to absorb everything in one go.
DoveArt 6 months ago
This is an excellent book on portraiture. The author/artist is incredibly talented and his portraits are awe-inspiring. In addition, he goes into great detail explaining his process step by step, including variations in stylistic choices, materials, poses, everything I could think of and more. If you can already draw relatively well, but want to grow, this book gives great insight. If you see the drawings on the cover, and it seems unreachable, I think this book will still be a fascinating look into a talented artist's process allowing a fresh perspective for your growth whatever stage you're in. Thanks to NetGalley for providing an ARC in exchange for an honest review.