25 Cool Jack O Lantern Pumpkin Faces

We curated 25 of the very best cool jack o lantern pumpkin faces so you can pick one and start carving in minutes.

1. Sleepy Eyes and Eight Lashes
Two closed crescent eyes with four little lashes apiece rest above a small oval mouth, while round dots on each side form rosy cheeks for a sweetly sleeping face. Every crescent, lash, dot, and the mouth is pierced through, so the tiny lash cuts do the expressive work. Cut the two big crescents first, then add the short lash strokes with a fine saw, keeping each one clear of its neighbor.
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2. Wink and Five Rounded Gaps
One eye is a jaunty upswept crescent wink while the other stays a wide triangle, set over a small diamond nose and a lopsided grin broken into five rounded gaps by chunky teeth. The eyes, nose, and mouth gaps are cut through, leaving the tooth shapes as attached skin between them. A medium carver should cut the five mouth gaps individually rather than one big mouth, which keeps every tooth solidly connected and the crooked smile intact.
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3. Unequal Eyes and Six Slashes
A menacing sneer built from two uneven glaring eyes, a small skull-like nose, a crooked mouth of jagged teeth, and three claw-slash marks raking each side of the face. All shapes pierce through, and the mismatched features do the intimidating. A medium carve; cut the six narrow slashes first with single confident strokes, then work the mouth teeth before opening the larger eye shapes.
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4. Winking Seven-Tooth Grin
A goofy winking jack-o'-lantern with one wide round eye, one squinting wink, a triangle nose, and an enormous grin broken up by a jumble of square and pointed teeth along both lips. Every feature is cut clean through so the mismatched expression beams from the whole face. At medium difficulty the mouth is the main event; cut the grin outline first, then shape each tooth individually, alternating sides so the lip strips stay supported.
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5. Wink and Barred Square Grin
One huge round eye stares while the other squeezes into a curled wink above a giant open grin packed with blocky square teeth, and freckle dots sprinkle each cheek. The eyes, mouth, and freckles all cut through the wall, with skin bridges left in place to form the teeth. Cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block stays anchored.
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6. Angry Eyes and Five Mouth Gaps
A grumpy jack-o'-lantern scowls with slanted, brow-slit eyes, a small triangle nose, angled cheek slashes, and a downturned mouth broken into square gaps. Every element is cut through, with the mouth's rind bridges creating the clenched, gritted-teeth effect. The thin brow and cheek slits earn the medium rating: make each slit with two close parallel cuts and pop the sliver out from inside the pumpkin, since pushing from outside can crack the narrow channel wider.
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7. Oval Eyes and Crescent Cheeks
This delighted face beams with two big oval eyes, a small triangle nose, crescent-shaped cheek accents, and an open grin showing a pair of stubby teeth, all dusted with tiny freckle holes. Every shape is pierced through, with the teeth left attached to the upper lip. Cut the delicate crescent cheeks with the tip of your saw only, since their thin curves are the easiest pieces to crack.
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8. Triangle Eyes and Six Diamonds
This elevated take on the traditional face pairs slanted triangle eyes topped with thin brow slits, a triangle nose, and a deep zigzag grin, then adds three small diamond cutouts on each cheek for extra sparkle. Every element is pierced through the wall. The brow slits and little diamonds are what push it to medium; cut the big shapes first, then handle each diamond with a narrow saw, working point to point so they stay crisp.
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9. Oval Eyes and Eight Cheek Dots
Big oval eyes sit under arched brows above a round button nose and a broad smile showing four blunt square teeth, with four freckle dots sprinkled on each cheek. The eyes, brows, nose, mouth, and dots are pierced through while the tooth bridges stay connected. Poke the eight small cheek dots first, then cut the large features, leaving the tooth bars until the end so they keep support.
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10. Unequal Eyes and Crooked Teeth
This lovably lopsided face pairs one round eye with one droopy crescent eye, a triangle nose, and a huge crooked grin full of uneven square teeth, plus a pair of dot dimples on each cheek. The eyes, nose, mouth, and dots are pierced while the mismatched tooth bars stay attached. It suits odd-shaped pumpkins perfectly; cut the tooth gaps in random sizes and the wonkier it looks, the better.
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11. Almond Eyes and Seven Teeth
A wide, low jack-o'-lantern face with sly almond-shaped eyes, a small triangle nose, and a long jagged mouth packed with alternating square teeth top and bottom. Everything is pierced through, and the horizontal layout suits squat, wide pumpkins. At medium difficulty the tooth row is the main work; cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block keeps support while you work.
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12. Left Wink and Six Cheek Wedges
A playful winking jack-o'-lantern: one big round open eye, one arched wink, a triangle nose, and a smiling mouth with blocky teeth, all framed by three thin whisker-like wedges slashed across each cheek. Every opening is cut through, and the six cheek wedges throw extra slivers of light. At medium difficulty, cut the large features first and finish with the skinny cheek slits, using a fine saw so each wedge tapers to a clean point.
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13. Tall Smile and Six Cheek Dots
A tall pumpkin design with arched happy eyes, an oval nose, three dot freckles on each cheek, and a huge open smile with four little teeth hanging from the top lip. Every shape is cut through, and the six small cheek dots add a sprinkle of glowing freckles around the grin. Punch the freckle dots with an apple corer or drill bit before opening the big mouth.
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14. Sloping Eyes and Unequal Fangs
A classic evil jack-o'-lantern with steeply slanted triangle eyes glaring downward and a wide jagged mouth of uneven fangs, some long and some short for extra menace. All shapes are pierced through for a fiery glow. Rated medium because of the zigzag mouth; cut each fang point with two clean strokes meeting at the tip, and bevel the eye edges outward so more light escapes upward.
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15. Angled Eyes and Seven Fangs
Two sharply slanted triangle eyes glare above a wide jagged mouth lined with seven pointed fangs, giving this face a classic menacing snarl. Every element is cut fully through, and the zigzag mouth does most of the work, so accuracy there pays off. Cut each tooth as two separate straight strokes meeting at the point instead of dragging the saw around the corner, and the grin stays razor sharp.
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16. Six-Slot Grin and Cheek Slits
Two arched, angry eyes glower above a huge crescent grin broken into a row of glowing tooth slots, with small slits flaring at each cheek. All the features are pierced through the wall, and the strips of rind left between the tooth openings become the dark teeth of the smile. Cut the mouth slots from the center outward and leave the narrow rind bridges at full thickness so the grin holds its shape.
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17. Angular Seven-Tooth Grin
A sharp-edged jack-o'-lantern face with slanted triangle eyes, an angular nose, and a wide jagged mouth broken into seven pointed teeth. Every shape is cut straight through the pumpkin wall, making a bright, high-contrast face that reads perfectly from the porch steps. It is a medium pattern because of the many small tooth points, so saw into each corner from both directions instead of twisting the blade to keep the tips sharp.
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18. Brows and Six Cheek Dots
A classic jack-o'-lantern face with slanted triangle eyes topped by separate angled brow cuts, a diamond nose, and a wide grin broken by six blocky teeth, plus three small round holes dotting each cheek. Every element is cut fully through so the whole face blazes at night. A solid medium project; drill or punch the cheek dots first while the wall is strongest, then saw the eyes, brows, and mouth.
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19. Arched Eyes and Seven Slots
This cheerful face pairs tall arched eyes, each with a round pupil left attached at the top, with a triangle nose and a huge grin broken by seven tooth slots. The eyes, nose, and mouth are pierced while the pupils and tooth bars remain as connected shell. The attached pupils are the trickiest part, so cut around each one carefully and leave a generous bridge so they stay anchored.
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20. Skeleton Face With Bone Teeth
This clever skull face swaps ordinary teeth for a row of four upright dog-bone shapes beneath two big oval eyes and a small triangle nose. Eyes, nose, and each bone tooth are pierced fully through so the whole skeletal grin glows. The rounded bone ends are the trickiest part of this medium carve; drill or poke a starter hole in the center of each bone, then saw outward so the knobby tips keep their shape.
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21. Swept Eyes and Melting Grin
A wicked jack-o'-lantern with two swept, flame-like eyes, a small notched nose, and an enormous melting grin whose edges drip and ripple across the lower half of the pumpkin. All features are pierced through, and the wavy mouth throws dramatic, uneven light. This is medium work with one long tricky opening, so carve the mouth in sections from the center out and leave the drippy lower points attached until the very end for support.
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22. Notched Brows and Jagged Grin
A characterful jack-o'-lantern with heavy notched brows sitting over sly almond eyes, and a huge open mouth whose top edge is a row of jagged zigzag teeth above a broad curling lower lip. Eyes, brow slits, and the mouth are all pierced through for a bright, expressive glow. At medium difficulty, the key move is cutting each zigzag tooth point cleanly; slice into every corner from both directions instead of turning the blade.
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23. One Eye and Two Upper Teeth
A goofy one-eyed jack-o'-lantern with a huge round eye topped by a dark pupil circle, a small triangle nose, and a wide smile broken by two chunky upper teeth. The big eye, nose, and mouth are cut through, while the pupil area keeps a disc of skin attached at the top for contrast. Support the teeth by cutting away from their narrow roots, since those two tabs carry the whole grin.
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24. Anxious Round-Pupil Frown
A hilariously worried pumpkin face with two big round eyes topped by drooping eyebrow arcs and a deep upside-down frown. Each feature is a pierced opening, and the round pupils stay attached as tabs inside the glowing eyes to give it that anxious stare. At medium difficulty the pupil bridges are the key detail; cut toward each tab rather than away so you do not snap them off.
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25. Round Pupils and Five Teeth
A big-eyed, grinning jack-o'-lantern face with round pupil tabs left inside each eye and five square teeth breaking up a wide smile. The eyes and mouth are cut clean through while the pupils and teeth remain attached to the rind as solid bridges. Those round pupils make this a medium carve, so pierce a relief hole beside each one first and saw toward it rather than levering the blade, which can snap the connecting tab.
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