Sep 14, 2026

Winking Square-Eyed Zigzag Pumpkin

One horizontal rectangular eye sits closed in a wink while the other is a tilted square with a preserved-skin pupil inside, and below them a wide zigzag grin bends the mouth into a dozen sharp peaks. The winking square-eye combination gives this jack-o-lantern pumpkin carving idea a playful asymmetry that tricks the eye. When laying out the design, establish the winking eye first as a long narrow slit and the open square eye second; the height difference between the two anchors the expression before you cut the complex zigzag mouth. Score the zigzag mouth points with a craft knife before sawing to prevent the thin peaks from cracking.

This is an AI-generated concept image: a realistic, carvable design idea rather than a photo of a finished carve. AI concepts are always labeled and sit out the leaderboard and the contest.

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Medium Faces Funny Classic Cutout

jack-o-lantern face funny cutout wink square-eye zigzag grin

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Want to try this?

Give this cheeky winking jack-o-lantern a try for a face that looks like it is up to something.

Some experience helps · Cutouts + zigzag scoring

Read our carving tips

Similar stencils

Browse similar funny face stencils to get the wink and grin spacing right.

Tools for this approach

Our suggestions for trying a similar carve. Start with what you already have.

Elmchee Pumpkin Carving Kit
13-piece kit with carrying case
Saws for the larger cutouts, plus a scoop for hollowing. Covers both jobs in one kit.
View on Amazon
Speedball 4131 Lino Cutter Set
Handle + 5 interchangeable cutters
Interchangeable cutters for peeling and shading the face. Useful for the finer details.
View on Amazon

A little extra help

Our tips for carving a similar design

The core trick here is the mismatched eyes: one long narrow slit reads as a closed wink while the other is an open tilted square that anchors the whole expression. The plan is to lay out both eyes first so the height difference feels intentional, then score and saw the zigzag grin carefully so the thin peaks stay strong. Since this is a concept image, treat it as a design you could recreate on a real tall pumpkin.

Written by PumpkinCarvingIdeas.com, inspired by the image above. These are our suggestions, not instructions from the uploader. This approach to the AI concept has not been tested on a real pumpkin.

From pumpkin to porch

Pick and prep a tall pumpkin
Choose a tall, oval pumpkin with a smooth flat area on the front for the face. Have an adult cut a lid from the bottom or the back rather than the top so the pumpkin sits stable on the ground. Scoop the insides and scrape the front wall until it is about one inch thick. A thinner wall makes the zigzag teeth much easier to cut cleanly.
Transfer the face layout
Tape your stencil flat and poke the outlines with a pin, or draw straight onto the skin with a washable marker. Establish the winking eye first as a long, gently curved narrow slit, then place the open tilted square eye lower and larger. That height difference is what sells the expression, so step back and check it before you commit. Mark the zigzag mouth last as a wide band of connected peaks.
Cut the winking slit and square eye
Start with the small, controlled cuts using a fine carving saw. Saw the narrow wink slit in one smooth pass, keeping it thin so it clearly reads as a closed eye. For the square eye, cut the outer shape but leave a small block of skin in the center for the pupil, which you will treat later. Take your time on the corners so the square stays crisp.
Score the zigzag before sawing
Draw the full zigzag, then lightly score along every line with a craft knife before you saw all the way through. Scoring gives the saw a guide and keeps the sharp peaks from cracking under pressure. Cut the mouth from the middle outward, freeing one triangle at a time and supporting each peak with your free hand. Save this large opening for near the end since it removes the most material.
Detail the pupil and eyebrows
For the preserved-skin pupil inside the square eye, use a lino or ribbon tool to peel just the top skin off the surrounding area, leaving the untouched pupil dark. If your design has a brow above the wink, carve it as a short separate slit to add attitude. Clean up all cut edges with the knife tip so the light spills through evenly.
Light it and photograph
Set a battery LED puck or string inside, never a candle, and close up the opening. Test in a dark room and rotate the light until the square eye and grin glow brightest. Set the pumpkin on gravel or a porch step at dusk and shoot slightly below eye level to catch the warm interior glow. Dab cut edges with petroleum jelly to slow drying if you want it to last a few extra days.

Gather your supplies

Check things off as you get ready.

Work on a stable surface, keep your free hand out of the cutting path, and have an adult handle sharp tools.

Three levels of light

Leave intact
The untouched face and the small pupil block inside the square eye stay dark
Peel & shade
The skin-peeled ring around the pupil glows a soft dim orange
Cut through
The wink slit, the open square eye, and the zigzag grin cut all the way through for the brightest light

Learn the carving basics

Before you start cutting

How do I keep the wink from looking like just a crack?

Give the slit a gentle curve and a little width in the middle so it clearly reads as a closed, happy eye. Placing it higher than the open square eye also helps the brain register it as a wink. Step back after cutting and compare the two eyes to confirm the expression lands.

Will the thin zigzag teeth break while I carve?

They can if you rush, which is why you score every line first and cut from the center outward. Support each peak with your free hand as you free the triangle next to it. Keeping the front wall around one inch thick also makes the peaks far less likely to snap.

How do I make the square eye pupil show up?

Leave a small block of skin in the center when you cut the square opening, then peel the thin outer skin from the area right around it. The peeled area glows dim while the untouched pupil stays dark, so the eye looks like it is looking at you. Keep the pupil small so plenty of light still escapes around it.