Welcome! This tutorial shows how to draw a winking male face in a cartoon style. It belongs to a series of 30 guides featuring the same character with different expressions. Think of it as an emotional journey, one wink at a time.
Drawing a Winking Male Face
This guide contains 16 illustrated steps that take you from basic construction lines to a completed winking male face. The asymmetry of a wink makes this expression trickier than a standard smile, but that’s exactly what makes it fun to draw. Consider this your crash course in cartoon flirtation, strictly artistic, of course.
Final Result: The Winking Expression
Here’s the finished winking male face you’ll create by the end
A winking face combines two different eye states simultaneously: one open, one closed. This asymmetry challenges your understanding of facial proportions and forces you to think about how the cheek pushes up on the closed side. After completing this winking male face tutorial, explore other expressions in this series, try drawing him shouting, surprised, grumpy, nervous or skeptical next.
Guide Structure: Color-Coded Steps
Every step in this tutorial uses specific colors to communicate what’s happening:
- Grey lines are your underlying sketch framework from initial steps
- Red lines highlight exactly what to add at the current step
- Black lines mark finished elements from previous steps
How to Draw a Winking Male Face: Complete Step-by-Step Guide
Drop a Comment and Show Off Your Drawing!
And that covers how to draw a winking male face from start to finish. Happy with your result? Leave a comment below with your feedback. If you’ve shared your winking guy on Instagram or Twitter, paste the link in the comments — other artists here would love to see your take on this expression, and constructive feedback helps everyone improve.
Don’t stop at winking! This character has 29 other expressions waiting for you. Practice drawing him laughing, annoyed, or confused to build a solid foundation in cartoon facial expressions.