16 Jack and Sally Painted Pumpkin Ideas That Look Straight Out of Halloween Town

Decorating pumpkins is one of those Halloween traditions that never gets old—especially when you add a little pop culture magic.

With Jack and Sally as your muse, even the simplest pumpkins can turn into mini masterpieces that feel like they’ve wandered out of Halloween Town.

Close-up of one or two hand-painted pumpkins featuring Jack and Sally kissing, placed on a tabletop.

This post rounds up playful, spooky, and downright charming painted pumpkin ideas inspired by The Nightmare Before Christmas. Whether you’re crafting with kids or decking out your porch, you’ll find plenty of inspiration to spark your spooky side.

Vintage-Inspired Couple

A pumpkin decorated with a black-and-white drawing of Jack Skellington and Sally from "The Nightmare Before Christmas," holding hands.

Black-and-white silhouettes bring Jack and Sally to life with charming simplicity. This classic design is perfect if you’re after something spooky-sweet with an old-school twist.

Patchwork Perfection

One to two pumpkins painted with colorful patchwork designs inspired by a dress, displayed on a tabletop with soft natural light.

Mimicking Sally’s iconic dress, these stitched-together color blocks turn a simple pumpkin into a bold, eye-catching centerpiece. They’re a playful mix of Halloween fun and crafty flair!

Vibrant Sally Style

Close-up photo of one or two pumpkins painted with red hair and green skin designs, placed on a tabletop with soft daylight.

Painted in rich teals and fiery red hair, this Sally-inspired pumpkin oozes Halloween magic. Her wide-eyed look and stitched smile bring personality to your fall décor instantly.

Romantic Silhouette

Close-up of one to two hand-painted pumpkins on a tabletop featuring Jack and Sally silhouette designs.

Captured in a tender gaze, Jack and Sally shine in this minimal yet expressive pumpkin art. It’s the perfect nod to gothic romance with a modern pop twist.

Playful Skeleton Pair

Two pumpkins are painted with cartoonish skeleton faces and colorful clothing inspired by "The Nightmare Before Christmas." One has long pink hair and a patchwork dress; the other wears a suit. Cream flowers and petals are nearby.

With bold outlines and soft florals nearby, this Jack and Sally duo blends spooky with sweet. Their cartoonish charm makes these pumpkins a standout for any Halloween table.

Butterfly Sally

Close-up of one to two pumpkins painted with colorful designs and butterfly accents on a tabletop.

Surrounded by fluttering butterflies, this dreamy Sally pumpkin feels like a soft, spooky fairytale. Her pastel palette and wide-eyed wonder make her the star of any Halloween setup.

Elegant Skeleton Pair

A pumpkin decorated with painted cartoon skeletons: a woman with long hair, a flower, and colorful dress, and a man in a tuxedo and top hat, reminiscent of Day of the Dead art.

Brimming with personality, this couple features sugar skull faces and charming vintage outfits. It’s a sweet nod to Día de los Muertos with bold color and personality!

Patchwork Smiles

Two pumpkins are painted with colorful patchwork patterns and feature big, cartoonish eyes, a stitched smile, and a small nose, inspired by Sally from "The Nightmare Before Christmas.

Covered in candy-colored panels, these stitched pumpkins bring playful Halloween cheer. Their wide eyes and happy grins are impossible not to love!

Spooky Sweethearts

Sealed with a nose boop, this Jack and Sally design captures their quirky love story. Soft colors and warm expressions make this a heart-melting Halloween highlight.

Patchwork Pumpkins

Close-up image of one to two pumpkins painted with colorful patchwork patterns inspired by Jack and Sally, placed on a tabletop with soft natural light.

Bright and playful, these pumpkins are painted in Sally’s iconic patchwork style with bold stitches. They instantly capture that quirky, handmade Halloween charm.

Striped Pumpkins

Close-up of one or two pumpkins painted with black and white stripes, placed on a simple tabletop under soft daylight.

Dramatic black-and-white stripes give these pumpkins a Jack Skellington vibe. They’re simple, striking, and perfect if you love spooky style without extra fuss.

Jack’s Grin

Close-up of one to two hand-painted pumpkins on a tabletop, featuring designs inspired by Jack Skellington and Sally with vibrant colors and a clean background.

Painted with bold black lines, this pumpkin shows Jack’s mischievous stitched smile. It’s a fun way to bring his spooky personality to your fall decor.

Jack and Sally

A blue pumpkin painted with characters Sally and Jack Skellington from "The Nightmare Before Christmas," sitting on a white surface with a green plant in the background.

Side by side, Jack and Sally stand out beautifully on this painted pumpkin. Their vivid colors and sweet expressions make it a centerpiece-worthy Halloween design.

Jack & Sally Love

A close-up of a hand-painted pumpkin featuring colorful silhouettes of Jack and Sally, sitting on a clean tabletop under soft daylight.

Full of color and charm, this pumpkin shows Jack and Sally together in vivid detail. Their expressions capture the sweet, spooky romance fans adore.

Patchwork Style

One to two brightly painted pumpkins with colorful patterns on a tabletop under soft daylight.

Painted in Sally’s stitched patchwork pattern, these pumpkins bring a playful handmade look. They’re perfect if you want something colorful yet unmistakably Nightmare Before Christmas.

Spooky Couple

A close-up of a hand-painted pumpkin featuring Jack Skellington and Sally designs, placed on a clean tabletop with soft daylight.

Side by side, Jack’s skeletal grin and Sally’s stitched smile pop against the orange pumpkin. Bold lines and bright colors make this design truly stand out.