If You Can Draw, You Can Create Portraits with the Timeless Beauty of Renaissance Masters

Discover the Step-By-Step “Analyze-First Approach” That Helps Artists Create Portraits with Dimension, Character, and Classical Beauty

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Award-winning artist Oliver Sin discovered one fundamental truth from 24 years of teaching thousands of students at Academy of Art University. 


As he watched student after student struggle with the same issues, a pattern emerged…


There’s a clear difference between artists who struggle…


…and those who can create award-winning portraits in less time.


It makes sense once you understand the mistakes most artists are making:


They approach portrait drawing backwards!


You see, they focus intensely on rendering features — the eyes, nose, mouth — hoping that somehow, if each part is drawn well enough, the whole will come together into a dimensional, lifelike portrait.


But it rarely does!


They’re left with flat, lifeless results that lack the dimension and character they envisioned — despite hours or even days of careful work.


Why?


It’s because they’re missing one crucial step:


Those who learn to see and analyze shapes, planes, and structure before putting pencil to paper create dramatically better portraits.


Not only that…


They do so in a fraction of the time!


This is why the “Analyze-First Approach” is such an important step in portrait painting.


It’s an approach that combines anatomical understanding, face shape analysis, and Renaissance techniques into a step-by-step system anyone can follow.


The difference is remarkable. 


Instead of spending days on portraits that never quite satisfy…


…Oliver’s students learn to create classical portraits with depth and character in hours instead of days!


How is this possible? 


Here’s the fundamental truth:


When you understand the underlying structure and learn to see shapes instead of features, you work with knowledge and purpose rather than trial and error.


And when you apply the Renaissance techniques of sfumato (for soft, smoke-like edges) and chiaroscuro (for powerful light and shadow) that Oliver will demonstrate using sepia and white pencil...


…you’ll be able to create portraits with the timeless beauty of classical masters.


And when you follow a clear, proven approach, you develop confidence.


That’s when painting becomes truly fulfilling and satisfying.


In Classical Portrait Drawing Simplified, Oliver shares this complete approach.


From properly sharpening your pastel pencils to creating portraits with dimension, character, and classical beauty. 


Whether you’re just beginning your artistic journey or looking to enhance your existing skills, this step-by-step course will transform how you see and draw portraits!

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 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.

Available in both Streaming and DVD Formats

Introducing Oliver Sin’s Brand NEW Pastel Course:

Classical Portrait Drawing Simplified

In this course, award-winning artist Oliver Sin shares his unique approach to portrait drawing — a method he has refined through 24 years of teaching experience.


You’ll discover how to create dimensional, classical portraits, applying Renaissance techniques to achieve results with depth, character, and timeless beauty.


Oliver guides you through every stage of the portrait drawing process, from properly sharpening your pastel pencils (a crucial first step many artists overlook) to creating finished portraits with professional quality.


At the heart of this course are two classical techniques popularized by Renaissance masters like Leonardo da Vinci:


Sfumato: Create soft, blurred edges without hard outlines, resulting in portraits with a natural, dimensional quality. Oliver shows you exactly how to achieve this effect with sepia pencils, creating the subtle gradations that bring a face to life.


Chiaroscuro: Master the powerful contrast that gives portraits their three-dimensional form. Oliver’s step-by-step guidance helps you understand not just how to render light and shadow, but why they work the way they do.


This course is perfect for:

  • Beginners — you’ll gain a solid foundation in portrait drawing fundamentals
  • Intermediate artists — you’ll learn to refine your skills and overcome common challenges
  • Advanced artists — you’ll deepen your understanding of classical techniques

Unlike other portrait drawing courses that focus solely on technique, Oliver’s approach emphasizes understanding before execution. 


You’ll discover:

  • How to analyze poses before drawing — Oliver’s No. 1 tip for success…
  • How to see shapes and planes rather than just features…
  • How to make your portrait drawings look truly three-dimensional…
  • How to simplify what you see for greater clarity and impact…
  • How to properly prepare your tools — especially sharpening pencils correctly…

As you build a solid foundation in anatomy and structure, you’ll develop the confidence that comes from true understanding. 


You’ll know when to follow the reference and when to make artistic changes.


To put it simply, Oliver’s gift is transforming struggling artists into confident creators.


And once you’ve accepted his gift, your transformation will begin…


“True growth in art comes through repetition, perseverance, and the willingness to try again — each attempt bringing them closer to mastery.” 

— Oliver Sin

Available in both Streaming and DVD Formats

INCREDIBLE TEACHER

Oliver’s a brilliant artist and so humble. It’s shocking to hear somebody at his level be so down to earth. Speaking as a student of his, I can say Oliver is an incredible teacher. His demos are life-changing to watch. He’s just amazing.

  • - @theRealDanHouse
    (Art community comment on Oliver Sin)

Your Lesson Plan!

Video length: Over 7 Hours

Introduction & Materials

In the introduction, Oliver Sin guides you through the essential materials needed for classical portrait drawing. You’ll learn about sepia pastel pencils, alternative sanguine conte crayon options, and proper sharpening techniques for optimal precision. Oliver demonstrates which paper colors and textures work best depending on your skill level, setting you up for success before you begin drawing. These foundational preparations are crucial for achieving the professional results you’ll see throughout the course.

Initial Sketch

This chapter covers the fundamental first steps of portrait drawing. Oliver demonstrates how to properly hold your pencil, prepare your paper, and sketch the boundaries of your portrait for proper composition. You’ll learn to identify positive and negative shapes for accurate drawing and apply the Andrew Loomis guidelines as a starting point. Oliver shows how to find the center of the face, place features accurately in a three-quarter-view portrait, and measure angles for lifelike accuracy. You’ll also discover when it’s appropriate to change what you see — creating rhythm with hair or adjusting earring shapes for viewer clarity.

Accurate Shapes

In this crucial chapter, Oliver reveals how to create an accurate blueprint for your portrait. You’ll learn to trace shapes from your reference and use that guide to refine your initial sketch. Oliver emphasizes his philosophy of “Look five times, draw once” and demonstrates why accurate tracing at this stage is essential for modifications to come. You’ll discover why accuracy of shape is the most important foundation, with Oliver reminding us that “every shape has room for improvement.” This methodical approach ensures your portrait has the correct proportions before you move to more detailed work.

Modify the Sketch: Shapes

This chapter takes accuracy to the next level as Oliver demonstrates how to turn both your sketch and your reference upside down to better see and draw accurate shapes. This counterintuitive technique helps you perceive shapes more objectively, without your brain’s preconceptions interfering. Oliver recommends modifying your sketch three to five times before proceeding further, showing how this iterative process leads to significantly improved accuracy. By the end of this chapter, you’ll have a refined blueprint that serves as the perfect foundation for adding dimensional form.

Drawing the Planes

In this chapter, Oliver teaches how to create form by identifying and drawing the different planes of the head and face. Before adding features, you’ll establish accurate proportions of head and face shapes — as Oliver explains, “Features are like the spot on an apple — you have to draw the apple with correct proportions first before drawing the spot.” You’ll learn to use dot and line techniques for enhanced accuracy and discover how to avoid creating “cartoon eyes.” By understanding the planes that define the form of the head, you’ll create a three-dimensional foundation that brings your portrait to life.

Accurate Planes

This chapter ensures your drawing of planes and features achieves professional-level accuracy. Oliver guides you through tracing planes from your reference as a comparative tool to refine your drawing. He reveals the one critical plane that most students forget — a common oversight that can undermine an otherwise strong portrait. Through this methodical verification process, you’ll develop a more sophisticated understanding of the face’s three-dimensional structure, creating a solid foundation for the dimensional quality that distinguishes master-level portrait drawings.

Modify the Sketch: Planes

This chapter is all about advanced refinement. Here, Oliver shows how to use your traced planes as a guide to bring greater accuracy to your drawing. He reminds you that as an artist, you can take creative liberties with your reference — demonstrating how he subtly changes angles and proportions to give drawings a more “classical” pose and feel. You’ll learn to emphasize turns of shape by darkening or lightening contour lines in key areas, making parts of the face come forward or recede. Oliver also addresses common tangents you might encounter and demonstrates professional solutions for a successful composition.

Anatomy Review 

This essential chapter covers the basic bones and muscles of the face and neck that underlie every portrait. Oliver demonstrates how understanding this anatomical structure helps you better comprehend the planes and lines you’re drawing. You’ll gain insights into how the skull, muscles, and skin work together to create the unique features of each face. This knowledge transforms your approach from simply copying what you see to truly understanding what you’re drawing — the foundation of Oliver’s “Analyze-First” philosophy.

Start with the Darks

With your perfect blueprint established, this chapter begins the exciting development of your portrait. Oliver demonstrates how to build shadow on your portrait while letting the toned paper serve as the light, creating chiaroscuro (the balance of light and dark that achieves a sense of volume). You’ll learn various ways to hold and use your pencil for different effects — from darkest darks to broad areas of consistent color to looser applications. Oliver reveals counterintuitive insights, like seeing the white of the eye as actually a dark, and demonstrates how to use sfumato to build volume with soft, smoke-like edges applied to 85%-90% of the portrait.

The Midtones

In this chapter, Oliver reveals the subtle art of midtone development — the crucial bridge between light and shadow in dimensional portraits. You’ll learn how midtones function as the “shadow of the lights” and why delicate handling is essential, particularly for female portraits, where overly dark midtones can age the subject. Through Oliver’s “Pencil Dancing” technique, you’ll master applying delicate pigment while visualizing simplified forms: the skull as an egg, the neck as a cylinder, and the head as a box with distinct light and shadow sides. Oliver demonstrates how he creates gentle turns of form through lost and found edges, and shows when to employ smudging for optimal softness in hair edges and cheek transitions — ensuring your portraits possess the harmonious, dimensional quality of classical drawing.

Take It to Finish

In this finishing chapter, Oliver guides you through the final stages that transform a well-structured drawing into a refined, dimensional portrait. You’ll discover precisely where to place the brightest highlights and why these strategic accents create the illusion of living skin. Oliver demonstrates his nuanced approach to rendering subtle highlights on lips (with insights on how this differs between male and female portraits) and reveals how to create delicate skin highlights using just the tone of the paper. You’ll learn where to add dark accents for maximum impact and how to incorporate “surprise elements” like earrings that enhance the portrait’s presence. These finishing techniques bring your drawing to life with classical depth and dimension.

Bonus Chapter: Shadow Review

This bonus chapter provides essential practice in understanding and rendering the shadows that create three-dimensional form. Oliver demonstrates the crucial differences between form shadows (which reveal the object’s inherent shape) and cast shadows (created when light is blocked). Through a practical exercise applying five distinct values to create a dimensional sphere, you’ll develop the foundational skills needed for convincing portrait drawing. This shadow review serves as valuable preparation or reinforcement for the techniques applied throughout the portrait drawing process, ensuring you can confidently create the light and shadow relationships that bring portraits to life.

Available in both Streaming and DVD Formats

What Oliver Sin Will Share Inside 

Classical Portrait Drawing Simplified

The “Analyze-First Approach” That Creates Dimensional Portraits

Discover the revolutionary method that Oliver developed through 24 years of teaching thousands of students at Academy of Art University — a technique so fundamental yet so often overlooked that it instantly separates master portrait artists from everyone else.


You’ll learn to see and analyze shapes, planes, and structure before putting pencil to paper, creating a solid foundation that eliminates guesswork. 


This approach transforms portrait drawing from a frustrating process of trial and error into a clear, structured journey that produces remarkable results

The Renaissance Techniques That Give Portraits Timeless Beauty

Oliver reveals the classical techniques of sfumato and chiaroscuro — the same approaches used by Leonardo da Vinci and other Renaissance masters — presented in clear, accessible steps that anyone can follow using modern materials.


You’ll discover how to create soft, smoke-like edges (sfumato) that give your portraits a natural, dimensional quality, and how to use light and shadow (chiaroscuro) to create powerful contrast and form. These techniques transform flat drawings into portraits with depth, character, and classical beauty.


The confidence this brings is immediate. Instead of hoping your portraits will have dimension, you’ll know they will. As Oliver says, “True draughtsmanship begins with knowledge; without it, the image remains but a shadow.”

The Toned Paper Trick That Saves Time While Enhancing Results

Learn the surprising approach to toned paper that Oliver teaches his students — using it not just as a background, but as an active participant in your portrait that serves as the mid-tone value, unifying your entire drawing while saving significant time and effort.


This principle works with any portrait subject and any skill level. Once you understand it, you’ll create portraits with greater harmony and richness in a fraction of the time traditional methods require — potentially completing well-structured portraits in hours rather than days.


Oliver’s students consistently report that after learning this principle, their portrait drawing process becomes not only more efficient but more enjoyable. Many have gone from avoiding portraits due to frustration to making them a central focus of their artistic practice, simply by applying this one insight.

GREAT TEACHER

Oliver is a wonderful artist to study. He is a great teacher as well.

  • — @blueeaselclub4689
    (Art community comment on Oliver Sin)

Here’s a small taste of what’s 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 transforms 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…


…including tons more tips and tricks you won’t get anywhere else

Available in both Streaming and DVD Formats

Discover Oliver Sin’s Pastel Painting Secrets in 

Classical Portrait Drawing Simplified!

If you’re someone who refuses to settle for flat, lifeless portraits that lack dimension and character…


And if you’re someone who knows there’s a real artist inside you waiting to create work with classical beauty and depth…


And if you’re someone who’s ready to finally create portraits that capture not just likeness but life and spirit…


Then you’ve already made the decision, otherwise you wouldn’t have read this far.


You’re not just considering another art course.


You’re choosing to become the artist you’ve always known you could be.


With Oliver Sin's instruction, you’re not just learning techniques — you’re stepping into your true artistic identity.

The artist who sees shapes and planes instead of just features.


The artist who creates portraits with dimension and classical beauty.


The artist whose drawings reveal both technical skill and deep understanding.


This is who you’re becoming.


And honestly?


Very few instructors have the level of mastery Oliver Sin brings to this teaching...


As a First Place winner in Drawing at the Portrait Society of America’s International Art Competition and recipient of the society’s prestigious Signature status, Oliver’s expertise is recognized at the highest levels.


Furthermore, if you live far away from San Francisco and can’t attend Oliver’s classes at Academy of Art University, this video is the next best thing.


It’s like having him as your “personal, in-house” instructor you can learn from over and over again — and it won’t cost you an extra penny.


Plus, you’ll see exactly which materials to use and how to prepare them properly so you won’t waste money on the wrong supplies or struggle with improper preparation.


So let’s take everything we’ve just discussed about how you’ll draw with newfound confidence...


…and how you’ll create portraits that truly capture dimension and character...


…and how you’ll finally become the artist who creates work with classical beauty and depth...


And let’s make it a reality for you.


The journey from frustration to fulfillment begins with a single step — understanding before drawing, analyzing before rendering, seeing before creating.


Oliver Sin’s Classical Portrait Drawing Simplified provides that understanding, that analytical approach, that way of seeing that transforms not just your portraits, but your entire artistic experience.

30-Day 100% Money-Back Satisfaction Guarantee!


After you go through this course, we want you to be completely satisfied and feel confident that you’ve improved your painting skills.


However, if after watching the video, you decide it’s just not for you, let us know within 30 days of purchase and we’ll refund 100% of your money.



Disclaimer

Results require practice and dedication. The techniques taught in this video need to be studied and implemented consistently to achieve improvement in your paintings. Individual results will vary based on experience level and amount of practice.

CHOOSE YOUR FORMAT!

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Though you can observe the techniques of any artist instantly by watching them demonstrate and by watching the videos repeatedly, please know that, though many artists offer insights that can help people overcome a lot of learning time, every artist learns at their own speed based on their own level of understanding. Painting and drawing bring great joy, though the joy may come from practicing various techniques over and over until you master them. We do not wish to indicate that you, or anyone, can skip the joy of practice and the challenges of getting better. Painting is a lifetime endeavor, and getting good does not typically happen rapidly, or instantly. Your results may vary. And please know that if at any time within 30 days you feel this video has not lived up to your expectations or its promise, we will happily refund your money.

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