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🎃21 designs · Updated for 2026

Preschool Toothy Grin Pumpkin Cutouts

Looking for preschool toothy grin pumpkin cutouts? You're in the right place. Print at 100% scale, tape it to your pumpkin, and poke through the lines with a pin.

Browse 21 designs ↓

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Print, tape it to your pumpkin, trace the lines, and start carving.

21 preschool toothy grin pumpkin cutouts

Beginner or pro, there's something on this page for you.

Easy

Sloping Eyes and Two Teeth

Two steeply sloping eyes scowl above a crooked grin holding two chunky square teeth, one notched into the top lip and one into the bottom. The eyes and mouth are pierced through, with the blocky teeth left as shell inside the mouth opening. Cut the outline of each tooth before clearing the rest of the mouth, and the asymmetry of the design means small wobbles only add to the attitude.

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Easy

Round and Square Eyes

A goofy lopsided face with one big round eye and one square eye, a small triangle nose, and a huge open smile interrupted by two buck teeth hanging from the upper lip. All shapes are cut fully through, and the mismatched eyes do all the comedic work. An easy, forgiving carve for kids and beginners; cut the smile last and leave the two tooth tabs of rind attached so they dangle into the glow.

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Easy

Triangle Eyes and Crescent Grin

A bold traditional design pairing two big triangle eyes with a wide crescent grin crossed by chunky square teeth top and bottom. All openings pierce the wall completely, so the face burns bright on any pumpkin, including green or white varieties. An easy carve with generous shapes; free the tooth gaps first, then cut the long smile curve in sections so the grin keeps its clean sweep.

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Easy

Wide Grin and One Broad Tooth

Made for short, squat pumpkins, this goofy face pairs two upswept triangle eyes with an enormous grin interrupted by a single broad tooth hanging from the top lip. The eyes and mouth are cut through, and the tooth is simply a block of shell left in place inside the smile opening. Cut around the tooth carefully on both sides before removing the mouth pieces so it stays firmly attached.

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Easy

Round Eyes and Two Short Teeth

Round eyes, a small triangle nose, and a broad grin with two stubby square teeth give this jack-o'-lantern a warm, welcoming personality. The eyes, nose, and mouth are cut through, while the two little teeth stay attached along the top of the smile. On this easy carve, cut carefully around each tooth so it remains anchored to the wall; everything else is simple circles and one flowing mouth curve.

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Easy

Leaning Eyes and Square Teeth

The timeless jack-o'-lantern: two leaning triangle eyes, a triangle nose, and a huge crescent grin interrupted by two blocky square teeth, one up and one down. Everything is a straightforward cut-through, which is exactly why this face has been a first-timer favorite for generations. Cut the mouth last and leave the tooth tabs generous; you can always trim a tooth thinner, but you cannot put pumpkin back.

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Easy

Wide Crescent and Short Teeth

The timeless jack-o'-lantern: two triangle eyes, a triangle nose, and a wide crescent grin broken by a few short square teeth left in place. Every shape is a straightforward cut-through, making this an ideal first carve of the season. Cut each triangle in three straight strokes that meet at the corners, and leave the teeth generous so they do not snap off.

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Easy

Happy Arches and Two Teeth

A joyful jack-o'-lantern with two happy crescent arch eyes, curved like eyes squeezed shut in a laugh, above a wide smile interrupted by two square teeth hanging from the upper lip. The eye arches and mouth are cut through while the two teeth remain as attached blocks of pumpkin wall. An easy, forgiving carve: cut the mouth outline first, then carefully saw around each square tooth so its corners stay crisp.

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Easy

Diamond Nose and Three Teeth

This is the timeless jack-o'-lantern: two triangle eyes, a diamond nose, and a wide crescent grin interrupted by three blocky square teeth, one hanging from the top lip and two rising from the bottom. Everything except the teeth is cut through, with the teeth left as standing tabs of shell. It is an easy, forgiving first carve; cut toward each tooth from both sides rather than sawing across it, so the tabs never take sideways pressure.

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Easy

Broad Grin with Five Teeth

Two chunky triangle eyes sit above a broad zigzag grin, where five blocky teeth alternate along the top and bottom of the smile. Everything cuts fully through, and the oversized features make this a great pick for a big pumpkin that needs to be seen from a distance. Carve the mouth as one long opening and leave each tooth attached to the rim, sawing the tooth notches last so they stay sturdy.

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Easy

Classic Grin with Two Teeth

The timeless jack-o'-lantern: two triangle eyes, a triangle nose, and a wide curved grin interrupted by two chunky square teeth, one on top and one on the bottom. Every feature is pierced straight through for maximum glow. This easy pattern is the classic first carve; angle each triangle cut slightly toward the center of the shape so the plugs pop out cleanly, and leave the tooth blocks generous so they do not snap.

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Easy

Wide Grin with Three Teeth

One enormous sweeping grin and nothing else: a wide crescent mouth interrupted by two blocky upper teeth and a single lower tooth, with no eyes at all for a mysterious, cheeky effect. The whole smile is cut through, so it pours light across the porch. An easy carve that goes quickly; remove the mouth in left and right halves around the teeth so the tooth tabs never take any strain.

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