We’ve all been there. You’re trying to doodle a quick note or decorate a card, and you decide to add a little flair. You go for the classic wink. But then, halfway through, something goes wrong. Instead of a charming, playful expression, your drawing looks like a pirate having a stroke or a yellow circle with a very concerning eye twitch. Honestly, it’s frustrating. Drawing a winky face seems like the easiest thing in the world until you actually put pen to paper and realize that the line between "cute" and "terrifying" is thinner than a 0.5mm felt-tip nib.
The wink is a universal symbol of shared secrets, inside jokes, and flirtation. It dates back decades in pop culture, long before Harvey Ball designed the iconic yellow smiley face in 1963 for the State Mutual Life Assurance Company. While Ball’s original design didn't feature a wink, the evolution of the "smiley" into the digital emoji era made the winking face a staple of human communication. Today, whether you call it a winkie, a smirk, or just a winking emoji, getting the proportions right matters if you want to convey the right mood.
The Secret Geometry of How to Draw a Winky Face
The biggest mistake people make is symmetry. Or rather, a forced lack of it. When you’re learning how to draw a winky face, you have to understand that the closed eye isn't just a flat line. If you draw one perfect circle for the open eye and a dead-straight horizontal line for the wink, the face looks "broken."
Think about what a human face actually does when it winks. The cheek pushes up. The eyebrow might dip slightly. The "closed" eye actually forms a gentle curve. Usually, this curve mimics the shape of a smile—an upward arc. If you draw the arc downward, the character looks like they’re sleeping on one side of their face or, worse, like they’re in pain. Keep that arc shallow. A deep semi-circle makes the face look like it’s squinting too hard.
The placement of the pupil in the open eye is the next dealbreaker. If the pupil is dead center, the face looks shocked. To make a winky face look actually engaged or mischievous, offset the pupil slightly toward the center of the face or toward the wink itself. It creates a sense of direction. It makes the drawing feel like it’s actually looking at someone.
Mastering the "The Smile-Eye" Technique
Most professional illustrators use what they call the "squinch." It’s a term popularized by portrait photographer Peter Hurley, but it applies perfectly to cartooning. When you draw the winking eye, you aren't just drawing a closed lid; you're drawing the tension of the muscles around it.
Try this: draw your circle first. Now, instead of placing the eyes in the dead center, move them up just a hair. This leaves room for a larger, more expressive mouth. For the winking eye, draw a "U" shape that is very wide and very flat. It should look like a bird flying in the far distance of a landscape painting.
Why Your Winky Face Looks Weird
Perspective is a liar. When we look at a 2D circle, we forget that it's supposed to represent a 3D head. If you place the wink and the open eye too far apart, the "face" loses its structural integrity. They should be level with each other. If one is higher than the other, the face looks tilted, which is fine if that’s what you’re going for, but usually, it just looks like an accident.
Another issue is the mouth. A winky face almost always needs a lopsided smile to work. If you use a perfectly symmetrical "U" for the mouth, it clashes with the asymmetrical eyes. Try pulling the corner of the mouth up slightly higher on the side where the eye is winking. This mimics real human facial anatomy. When we wink, the muscles in our cheek pull the corner of our mouth upward.
Don't forget the eyebrows! Eyebrows are the unsung heroes of expression. For a classic winky face, keep the eyebrow over the open eye neutral, but drop the eyebrow over the winking eye just a little bit. It sells the "scrunch" of the wink. Without the eyebrow movement, the wink feels static and fake.
Essential Tools for a Clean Sketch
You don't need a $2,000 Wacom tablet to do this. A simple No. 2 pencil and a decent eraser are better for practicing because they allow for "ghosting"—drawing very light lines that you can easily rub out once you’ve found the right shape.
- Pencils: Use an H grade for the initial circle so the lines are light.
- Liners: Once you're happy, go over it with a black felt tip or a Sharpie.
- Paper: Something with a bit of "tooth" or texture helps control the pen.
Step-by-Step Breakdown for Beginners
Start with the circle. Don't worry about making it perfect; a slightly wobbly circle actually has more character. Use a light touch. If you’re struggling with circles, trace a coin or a jar lid. It’s not cheating; it’s a shortcut used by pros.
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Next, find your centerline. Draw a very faint vertical line down the middle and a horizontal line across the center. Your eyes will sit on that horizontal line. This ensures you don’t end up with one eye on the forehead and the other on the chin.
Now, for the eyes. On the left side, draw a simple oval or a circle. On the right side, draw your "wink." This is that shallow upward arc we talked about. Make sure the width of the arc is roughly the same as the width of the open eye. If the wink is too short, it looks like a scar. If it's too long, it wraps around the side of the head.
The mouth comes next. Start the mouth line slightly below the center. Curve it up. If you want that "cheeky" look, add a tiny little "tick" or dimple line at the end of the smile. It’s a small detail, but it adds a massive amount of personality.
Advanced Variations: Beyond the Standard Emoji
Once you’ve mastered the basic how to draw a winky face method, you can start playing with style. The "Anime Wink" is a popular variation. In Japanese manga styles, the winking eye is often represented by a sharp, stylized ">" shape or a very thick, curved lash line. The open eye is usually massive, with multiple highlights to indicate light reflecting off the iris.
Then there's the "Grinch Wink." This involves a much more exaggerated facial scrunch. The mouth is usually pulled way to one side, and the winking eye is surrounded by "crows feet" or wrinkle lines. This is great for more complex characters or editorial cartoons where you want to show a bit of mischief or even villainy.
Adding Color and Depth
Coloring your winky face is where it really starts to pop. If you're going for the classic emoji look, you aren't just using one shade of yellow. Use a slightly darker orange or tan around the edges of the circle to create a "sphere" effect. This is called radial shading.
For the eyes, if you're using color, a tiny white dot in the corner of the open eye (a "catchlight") makes the character look alive. Without that white dot, the eyes can look flat or "dead." For the winking eye, you can add a very faint shadow just below the arc to represent the eyelid's thickness. It's subtle, but people notice it subconsciously.
Common Pitfalls and How to Fix Them
- The "Sad Wink": This happens when the arc of the wink points down like a frowny face. Flip it over!
- The "Staring" Eye: If the open eye is a perfect circle with a tiny dot in the middle, it looks creepy. Make the pupil larger or add a slight lid line at the top of the eye.
- The Floating Face: Sometimes the features are too small for the head. Ensure your eyes and mouth take up about 50-60% of the interior space of the circle.
Drawing is mostly about observation. Look in the mirror and wink at yourself. Seriously. Notice how your skin moves. Notice how your eye doesn't actually disappear; it just changes shape. The more you understand the "why" of a face, the easier the "how" becomes.
Putting it Into Practice
If you're doing this digitally, use layers. Draw your circle on Layer 1, your guide lines on Layer 2, and your final face on Layer 3. This allows you to delete the messy parts without ruining the whole drawing. If you're working on paper, keep a "test sheet" next to you to practice the curve of the wink before committing it to your main drawing.
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Art is subjective, but the "logic" of a face is pretty consistent. A winky face is a shorthand for a complex human emotion. It’s a bridge between words and feelings. Whether you’re drawing on a whiteboard during a meeting or sketching in a notebook, those three or four lines carry a lot of weight.
Actionable Next Steps:
- Grab a post-it note and draw five winky faces in a row, changing only the mouth shape on each one to see how it alters the mood.
- Experiment with "line weight." Try drawing the wink with a much thicker line than the open eye; see how it emphasizes the action of the wink.
- Study the "Emoji 15.1" standards or look at the Apple vs. Google versions of the winking emoji to see how professional designers handle the spacing of the features differently.
- Try the "Reverse Wink" by drawing the face from a side profile (three-quarters view). This requires "foreshortening," where the eye further away from the viewer is narrower than the eye closer to the viewer.