Let’s be honest. Most people who try to learn how to draw a Cheshire Cat end up with a weird, lumpy feline that looks more like a taxidermy accident than a whimsical Lewis Carroll creation. It’s frustrating. You want that iconic, mischievous glow, but you get a sourdough loaf with teeth.
The problem isn't your lack of talent. It’s that most tutorials treat the Cheshire Cat like a standard tabby, which he absolutely is not. He’s a metaphysical entity. He’s a cloud of sarcasm with whiskers. If you approach the page trying to draw "a cat," you’ve already lost the battle. You have to draw the vibe first.
I’ve spent years sketching characters from the public domain versions of Alice's Adventures in Wonderland, and if there is one thing I’ve learned, it’s that the smile is the foundation, not the finishing touch. Most artists leave the mouth for last. That is a massive mistake. You have to build the entire skeletal structure around that crescent moon grin.
The Anatomy of a Disappearing Act
Standard feline anatomy suggests a triangular muzzle. Forget that. The Cheshire Cat’s face is basically a circle bisected by a massive, oversized horizontal curve. Think of it like a lemon wedge.
When you start your initial sketch, don't worry about the fur. Use light, gestural lines. You want to establish the "C" curve of the spine. Whether he’s lounging on a branch or floating in mid-air, that spine is usually arched. It conveys a sense of lazy superiority.
Sir John Tenniel, the original illustrator for Carroll’s 1865 masterpiece, gave the cat a very human-like face. It’s creepy. It’s unsettling. And it’s exactly why the character works. If you look at Tenniel's original woodblock engravings, you’ll notice the eyes are spaced incredibly far apart. This wide set gives him that "all-seeing" look. If you put the eyes too close together, he just looks like a hungry housecat.
Why the Grin is Technically Difficult
The grin isn't just a line. It’s a volume. To get the how to draw a Cheshire Cat process right, you need to understand the "cheek pinch." When a person—or a magical cat—smiles that wide, the cheeks push upward, partially squinting the lower eyelids.
Draw two large circles for the cheeks first.
Then, wrap the mouth line around those spheres. This creates a 3D effect. If you just draw a flat line across a circle, he’ll look like a cardboard cutout. You want him to look like he’s about to tell you a riddle that makes your brain hurt.
Mastering the Stripes and Texture
Coloring or shading this beast is where most people get bored and messy. Whether you’re going for the classic 1951 Disney pink-and-purple palette or the more muted, Tim Burton-inspired grey and teal, the stripes must follow the contour of the body.
Stripes are not flat ribbons. They are "wrap-around" indicators.
If the cat’s belly is round, those stripes should curve like the lines of latitude on a globe. If they are straight, the cat will look flat. I always recommend using a "broken line" technique for the stripes. Don't draw solid blocks of color. Instead, use short, flicking strokes that mimic the texture of fur. It takes longer. It’s tedious. But the result is a creature that looks like you could actually pet it (even if it might bite your hand off).
The Eyes: Windows to Nowhere
The pupils are key.
Most versions of the Cheshire Cat feature large, yellowish or green irises with vertical slit pupils. However, if you want him to look truly maniacal, try making the pupils slightly different sizes. It’s a subtle trick used in character design to indicate instability or "madness."
Keep the highlights consistent. If your light source is coming from the top right, both eyes need a tiny white dot in the top right corner. It sounds basic, but you'd be surprised how many people forget this and end up with a cross-eyed cat.
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Common Pitfalls When Learning How to Draw a Cheshire Cat
I see the same three mistakes over and over.
First, people make the ears too small. The Cheshire Cat needs large, expressive ears to balance out that massive jaw. Think of them like satellite dishes catching the gossip of Wonderland.
Second, the teeth. Please, for the love of art, do not draw every individual tooth with a hard black outline. It makes him look like he has a mouth full of chiclets. Instead, draw the general shape of the tooth row and use very light shading to suggest the gaps between the teeth. The focus should be on the shape of the mouth, not the dental work.
Third, the tail. The tail should be an afterthought in terms of placement but a priority in terms of "fluff." It should be thick—thicker than you think. A thin tail makes him look scrawny and weak. A thick, bushy tail makes him look powerful and mysterious.
The Secret of the "Fade Out" Effect
Since this cat is famous for disappearing, your drawing should reflect that fluid nature. If you’re working with pencils, use a blending stump (or your finger, honestly) to smudge the edges of the lower body.
If you're digital, use a soft eraser or a "cloud" brush at 20% opacity.
The goal is to make it unclear where the cat ends and the air begins. This is why the Cheshire Cat is such a great subject for practicing soft edges versus hard edges. The teeth and eyes should be sharp and high-contrast. The rest of the body can be soft and hazy. This visual hierarchy guides the viewer's eye exactly where you want it: the face.
Equipment Check
You don't need a $3,000 Wacom tablet for this. Honestly, a 2B pencil and a decent piece of sketchbook paper are better for learning the fundamentals of the curves. If you are going digital, use layers. Put your "sketch" layer in light blue, your "ink" layer in black, and your "glow" layer on top of everything using a "Linear Dodge" or "Screen" blend mode.
Bringing the Character to Life
Don't just draw him sitting there. Give him a personality.
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Is he mocking Alice? Is he bored?
Tilt the head. An angled head immediately adds character. A perfectly vertical head is boring. By tilting the head 15 degrees to the left, you imply he’s questioning the viewer's sanity. That is the essence of Wonderland.
The Cheshire Cat isn't a pet; he’s a philosopher who happens to have fur. If your drawing feels too "cute," sharpen the claws or make the eyebrows more arched.
Actionable Next Steps for Your Sketchbook
You aren't going to master this in one sitting. Art is a muscle. Here is how you actually get better at this specific character over the next week:
- The Smile Sprint: Spend ten minutes just drawing mouths. Don't draw heads. Don't draw eyes. Just draw various widths of crescent-shaped grins with suggested teeth.
- Contour Study: Take a photo of a real cat and draw stripes over it, making sure they follow the "3D" wrap of the body. This trains your brain to see volume instead of flat shapes.
- The "Tenniel" Challenge: Look up the original 1865 illustrations. Try to copy one exactly. It will feel stiff and weird, but it will teach you how to handle the intricate cross-hatching that gives the cat his Victorian "creepy" factor.
- Negative Space Practice: Try drawing the cat by only drawing the stripes and the features, leaving the rest of the body as the white of the paper. It’s a fantastic exercise in "less is more."
Go grab a pencil. Start with the widest, dumbest-looking curve you can manage in the middle of your page. That’s your anchor. Everything else—the fur, the ears, the madness—will follow that one single line. Success in how to draw a Cheshire Cat comes down to embracing the absurdity of the shape before you worry about the details of the fur. Just keep your lines light until you're sure of the placement, and don't be afraid to erase. Even the cat disappears sometimes, so your lines can too.
Focus on the contrast between those sharp, predatory teeth and the soft, rounded cheeks. If you can nail that juxtaposition, you've captured the character. Now, stop reading and start sketching. The page isn't going to fill itself, and that cat isn't going to wait around forever before he vanishes entirely.