Oliver Sin: 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!

Meet Your New Instructor, Oliver Sin!

Oliver Sin is an alumnus of Academy of Art University in San Francisco, California, where he earned his BFA in Illustration. 

After graduating in 1996, he began his career as a concept artist in the computer game industry at LucasArts. 

In 2001, Oliver returned to his alma mater, where he has since served as an instructor in the School of Fine Arts and 2D Animation.

His artistic achievements have earned him significant recognition in the portrait art world. 

In 2021, Oliver’s vine charcoal portrait of his father won First Place in Drawing at the Portrait Society of America’s International Art Competition. 

In recognition of his consistent achievements in fine art portraiture, he was awarded Signature status by the Portrait Society of America in 2022.

Oliver is also the author of two instructional art books, Drawing the Head for Artists and Facial Expressions for Artists, both published by Rockport Publishers. 

His first step-by-step educational DVD, Portrait Drawing Simplified, was released by Streamline Publishing in April 2022.

Since 2011, Oliver has had the privilege of studying under several renowned contemporary artists — Zhaoming Wu, Henry Yan, and Huihan Liu — whose mentorship has deeply influenced his artistic journey. 

Their guidance inspired him to pursue a more refined understanding of human expression and to approach portraiture with a heightened sensitivity to form, structure, and composition.

Oliver’s teaching philosophy is rooted in the belief that true understanding must precede rendering. 

As he often reminds his students, “What is not understood cannot be faithfully portrayed.” And “True draughtsmanship begins with knowledge; without it, the image remains but a shadow.”

This philosophy has shaped his approach to portrait drawing, which emphasizes analyzing before drawing and understanding the underlying structure before rendering details.

Oliver has been a professional art educator at Academy of Art University in San Francisco since 2001. 

Over the course of his 24 years of teaching, he has studied under master artists and continuously refined his own approach to portrait drawing.

The method he shares today is the result of decades of experience — distilled into a clear, accessible process designed to help students learn with ease and confidence. 

His goal is to demystify the art of portraiture, offering a pathway that is both efficient and deeply rooted in classical principles.

Students and followers consistently describe Oliver’s teaching approach as “easy to understand” and his results as looking “effortless.” 

His ability to “simplify what you see” and his deep knowledge make his instruction accessible and effective for artists at all levels.

 What You’ll Discover Inside:

• 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…
• 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…
• 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
• 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...
• 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…
• 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...
• 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…
• 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…
• 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...
• 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...
• 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)...
• 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...
• 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…
• 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...
• 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...
• 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...
• 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...
• 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…
•  …and so much more!

Chapter Breakdown 

Introduction & Materials

Initial Sketch

Accuracy of Shape

Modify the Sketch: Shapes

Drawing the Planes

Accuracy of Planes

Modify the Sketch: Planes

Anatomy Review

Start with the Darks

The Midtones

Take it to Finish

Extra Bonuses:

• Shadow Review:Review differences between form and cast shadows as you apply a range of five values to create a 3D sphere; practice as needed before applying to your portrait.
• High Speed View for your painting convenience
• Exhibit of Oliver Sin’s works for your creative inspiration
• Interview with Oliver Sin by Eric Rhoads for insights and motivation