Portrait Drawing Simplified
In Portrait Drawing Simplified, Oliver Sin freely shares what he has learned in his many years of study through school, college, the movie industry, and in his professional teaching career to help you advance your skill at an incredibly quick rate.
Oliver will show you how to overcome your struggles with portraits and he’ll demonstrate exactly how to avoid common mistakes. He’ll lead you to remember why you wanted to try portrait work in the first place by bringing you back to the fun of it all.
Among many achievements and awards, Oliver has had his beautiful, captivating portraits featured on the cover of Time Magazine,twice! He also worked for George Lucas as a concept artist before moving on to an incredibly successful teaching career that spanned 20 years.
If you’ve ever had any desire at all to create breathtaking portraits, don’t pass up this rare opportunity to learn from Oliver Sin.
If you’ve tried portraits and you’re unhappy with the results, you’ll find Oliver to be a great encouragement. He openly admits his own failures and what he’s done to rectify them. This alone will slice years off of your own learning and practice curve.
Trust us when we say that Oliver Sin has many things to teach you and you don’t want to pass up an opportunity to learn from him. You’re sure to see amazing results when you incorporate Oliver’s techniques into your own portrait drawings.
Chapter Outline
- Introduction
- Materials & Tools–brief review of vine charcoal and other drawing tools
- Head Drawing vs. Portrait Drawing:
Demonstration 1: Head in Profile
- Head in Profile: Proportions
- Brief review of how to see and capture the accurate proportions of the head and face using a photo of a woman in profile for reference.
- FOR BEGINNERS– Oliver recommends starting with a profile drawing before tackling any other view of the head.
- Learn how to hold and use vine charcoal and WHY PROFESSIONAL ARTISTS use this as a tool when laying in the construction of the head
- TIP to use contour lines to draw so your portrait is MORE ORGANIC, LESS CARTOONY
- How to see and draw ACCURATE ANGLES
- How to hold your “measuring tool” (Oliver uses a brush handle) for best results
- TIPS on Standard proportional guidelines (using Andrew Loomis’ guidelines)
- Head in Profile: Initial Shapes
- Discuss what a shape is–a closed contour, and the importance of seeing shape
- Organic vs Geometric shapes, and how the face has many geometric shapes
- Discuss the importance of accuracy of “shape” in order to get the likeness of models
- Oliver Demonstrates how to draw a very basic profile of a woman from a photo using “shapes” drawn onto the proportional guidelines he drew in previous chapter
- The more sketching lines you use here at this shape-making stage of a head drawing, the better–will help you get accurate
- Head in Profile: Accurate Shapes
- Continue the profile drawing along with Oliver and learn step by step TIPS for drawing with accuracy
- Why it's OK TO TRACE–Oliver encourages his students to learn by tracing
- Think of it as a Stepping Stone to better drawing
- Use your tracing to then look at your sketch and see where your Initial Shape drawing needs improvement
- Turn the reference and your drawing UPSIDE DOWN – the second pass at finding accurate shapes
- By the end of this chapter you will have a BLUEPRINT for the rest of your drawing
- Head in Profile: Planes of the Head
- Using a John Asaro model of the head, Oliver explains and draws the plane changes on his profile shape drawing
- ACCURACY of Shape and PLANE CHANGE are most important part for new portrait artists
- Plane changes are smaller shapes of the head / face that will give even more accuracy to your portrait drawings
- Learn The ONE PLANE CHANGE BEGINNERS MISS and how to make sure you don’t
Demonstration 2: Head in ¾-View
- Head in ¾-View: Proportions
- Once you draw a profile view, you are ready for this MORE COMPLICATED pose
- Oliver reminds us to OBSERVE THE MODEL FIRST before drawing
- He reviews this pose and the IDEAL LIGHTING to use to give most contrast to the features
- Oliver reviews the GESTURE of this pose–the tilts and angles that you need to observe so you can capture them accurately
- Learn what PAPER is best to use to capture the the texture of the hair
- Head in ¾-View: Initial Shapes
- Oliver Demonstrates how to draw a the initial shapes onto the proportional guidelines of the ¾ view of the man he drew in previous chapter
- Reminders to focus on shape of HAIR versus lines and individual hair
- Accuracy of shapes will make or break your drawing
- How to AVOID a FLOATING HEAD portrait
- Head in ¾-View: Accurate Shapes
- Continue the ¾-view head drawing along with Oliver and Learn step by step TIPS for drawing with accuracy using the tracing paper technique we first tried in the profile demo
- Learn WHICH SHAPE is Key to a good drawing
- Learn how to see shapes ABSTRACTLY
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“Details of a face are just a Spot on an Apple” – aka, details are not important
- Head in ¾-View: Planes of the Head
- Using the John Asaro model we were introduced to in the previous demonstration of the profile, Oliver explains and draws the plane changes on his ¾-view head shape drawing
- Head in ¾-View: The Final Blueprint
- The 5th pass to make sure your shapes and drawing are as accurate as can be
- Head in ¾-View: Render the Values
- How to hold the charcoal as you add value shape by shape
- Why it is IMPERATIVE to use the same stick of charcoal for the entire value rendering stage (oliver recommends finding a nice long piece and breaking into 1-inch smaller pieces so ALL your values come from the same stick
- Learn How to render the head with the 5-VALUE SYSTEM” using vine charcoal
- Tips on what to watch out for such as “the side plane of the nose is very narrow,” and “don't worry about the highlights yet,” learn how to make corrections if needed, etc.
- How to achieve the darkest darks, easily remove charcoal, and when it’s okay to blend and when you should not
- Head in ¾-View:Develop the Values of the Face
- Deepen shadows–how to AVOID CHALKY BRUSHSTROKE (oliver refers to his vine charcoal application as a brushstroke even though he is using charcoal without a brush)
- It’s never too dark
- The ONLY time its ok to use a contour LINE, versus laying down value as shape
- Your FINGER as an eraser
- Kneaded eraser to remove highlight shapes
- Rendering is all about the RELATIONSHIP of the values
- SQUINT
- PATIENCE, PATIENCE, PATIENCE
- STEP BACK
- Head in ¾-View: Develop the Values of the Facial Hair
- When it's OK to EXAGGERATE
- TIPS for drawing realistic Facial hair
- AN UNEXPECTED TOOL you need to draw facial hair
- When to add WRINKLES and how
- Head in ¾-View: Push the Darks & Lights
- Remember to use CROSS HATCHING to avoid chalky darks
- Develop the ear
- Tips to Create the ROUNDNESS of the eye
- Start highlighting the hair
- Head in ¾-View: Redefine the Face
- Adjust value relationships: Redefine darks and bring up lights
- Pay attention to plane changes
- Head in ¾-View: Final Adjustments
- Loose, soft impression of facial hair
- Learn how to keep hair EXPRESSIVE versus drawing every strand
- TRICKS to give the beard realistic volume
- Why only 15% of your edges should be hard–where those need to go and why
- When to add FIXATIF and why/how/where
- Head in ¾-View: Add Dark Accents
- WHEN and Where to put these and WHY
- What you need to do BEFORE you add Dark Accents
- How to AVOID a LONELY ACCENT
From the artist:
“As a passionate art educator, I’d like to dedicate this video to the many students whom I have taught, but also have learned from. I have tried to teach students what I know, but students have opened my eyes to what I wouldn’t have otherwise seen.
Classical Portrait Drawing Simplified
Discover Oliver Sin’s SIMPLIFIED Classical Portrait Approach and Start Drawing Like the Renaissance Masters!
Transform your portrait drawing with Oliver Sin’s “Analyze-First Approach.”
This brilliant approach helps artists create classical portraits with depth and dimension in hours instead of days.
In this comprehensive course, award-winning artist Oliver Sin shares his unique method for portrait drawing that emphasizes understanding before rendering.
You'll learn how to analyze shapes, planes, and structure before putting pencil to paper — the crucial first step that separates master portrait artists from everyone else.
Oliver guides you through a structured, step-by-step approach rooted in classical techniques, making this traditional medium accessible to artists of all levels.
You’ll also discover:
- How to apply Renaissance techniques of sfumato and chiaroscuro to create portraits with soft, natural edges and powerful light and shadow…
- A thorough study of head anatomy, beginning with the structure of the skull, the underlying musculature, and the simplified planes of the head
- How to analyze your subject’s features like a surgeon to guarantee your portrait’s success…
- Techniques for rendering challenging areas like hair and creating soft edges that bring your portraits to life…
- …and so many more incredible insights!
A First Place winner in Drawing at the Portrait Society of America’s International Art Competition, Oliver Sin brings 24 years of teaching experience to this course, distilled into a clear, accessible process.
This is your chance to learn from a true master of his craft!
What You’ll Discover Inside:
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The counterintuitive “Analyze-First” approach that transforms portrait drawing from a frustrating guessing game into a clear, structured process producing remarkable results in a fraction of the time...
- The Renaissance secret of sfumato (Italian for “smoke-like”) that creates soft, blurred edges without hard outlines — the same technique Leonardo da Vinci used to create portraits with natural, dimensional qualities…
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Why focusing on features instead of shapes keeps most artists trapped in a cycle of disappointment — and the simple shift in perception that instantly improves your portraits’ dimension and character…
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The surprising role of toned paper as an active participant in your portrait that unifies your drawing while saving significant time and effort… and how to use sepia and white pencils for masterly effects
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The often-overlooked preparation step that creates precision and control that transform your drawing experience; most art courses ignore this, but Oliver considers it essential...
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The exact three-step “Shape-Planes-Structure” method that builds portraits from fundamental forms to finished details — creating a solid foundation that eliminates guesswork and produces consistent results…
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A precise technique for rendering hair that solves one of the biggest challenges for portrait artists — capturing the organic flow and dimensional quality without creating flat, lifeless strands...
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The specific “Look five times, draw once” methodology that dramatically reduces mistakes and corrections — saving you hours of frustration while creating more accurate, confident portraits…
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A step-by-step approach to analyzing faces before drawing that identifies the essential shapes, planes, and structures most artists miss — creating portraits with professional-level dimension and character…
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The detailed process for creating soft edges for lips without the hard outlines that instantly mark a portrait as amateurish — a subtle technique that significantly elevates the quality of your work...
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Why turning your reference and drawing upside down reveals shape errors you’d never notice right side up — and how this simple technique can transform the accuracy of your portraits almost immediately...
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What Oliver discovered after 24 years of teaching thousands of students that separates those who create dimensional, lifelike portraits from those who struggle with flat, lifeless results (hint: it happens before pencil touches paper)...
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The counterintuitive truth about the white of the eye in portrait drawing that surprises even experienced artists — and how understanding this principle transforms the realism of your portraits...
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The one plane most students forget when drawing faces that’s absolutely crucial for accuracy — once you know it, you’ll never make this common mistake again…
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Why Oliver recommends modifying your sketch three to five times before proceeding to the next stage — and how this seemingly time-consuming step actually saves hours while dramatically improving results...
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Master the classical techniques of sfumato and chiaroscuro to create portraits with soft, smoke-like edges and powerful light and shadow — the same approaches used by Renaissance masters...
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Learn to see and draw accurate shapes and planes rather than just features — developing the fundamental skill that separates master portrait artists from everyone else...
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Develop the ability to analyze poses before drawing — Oliver’s No. 1 recommendation for portrait drawing success and a skill most art instruction completely overlooks...
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PLUS: Discover how to use lost and found edges to create visual interest and dimensional quality — allowing some edges to disappear into shadow while others remain defined…
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…and so much more!
