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Smiling Pumpkin Hats

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Pink Glowing Jack-O-Lantern Smiling Pumpkin Hat
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Description: This feminine girly pink jack-o-lantern pumpkin is so happy that she is glowing with excitement for the upcoming Fall Autumn Halloween season ready to go trick or treating and eat lots of candy corn, chocolate and other spooky treats! The mask zooms in to show your pumpkin smile to celebrate Halloween and makes the perfect accessory for your costume. Instagram@ Artbydebcamp Facebook@ Art by Deborah Camp

Tags: carved pumpkin, halloween, halloween costume gift, halloween gifts, jack o lantern

Pink Glowing Jack-O-Lantern Smiling Pumpkin Hat

by Art by Deborah Camp

$12 $19

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Smile and skull Hat
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Description: Smiling Skull

Tags: cute, funny, happy, smile, smile face

Smile and skull Hat

by gggraphicdesignnn

$12 $19

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Halloween Pumpkin, Smiling Pumpkin, Trick Or Treat Hat
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Description: Cute, fun and adorable design with orange pumpkin. Modern and trendy gift, perfect for Halloween.

Tags: boo, carved pumpkin, cute pumpkin, happy halloween, hocus pocus

Halloween Pumpkin, Smiling Pumpkin, Trick Or Treat Hat

by Strawberry and Hearts

$12 $19

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Smiling Pumpkin Spooky Halloween Hat

Description: Smiling Pumpkin Spooky Halloween

Tags: black cat, cute halloween, funny halloween, funny pumpkin, ghost

Smiling Pumpkin Spooky Halloween Hat

by DasuTee

$12 $19

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Smiling Pumpkin Spooky Halloween Hat

Description: Smiling Pumpkin Spooky Halloween design featuring smiling-pumpkin-spooky-halloween, black cat, cute halloween, funny halloween, funny pumpkin. Perfect gift for fans.

Tags: black cat, cute halloween, funny halloween, funny pumpkin, ghost

Smiling Pumpkin Spooky Halloween Hat

by Forest_Deer

$12 $19

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Creepy Smiling Pumpkin Hat
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Description: halloween style t shirt design flat goth metal rock band style halloween pumpkin smiling

Tags: creepy, halloween, hardcore, horror, metal

Creepy Smiling Pumpkin Hat

by crissbahari

$12 $19

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Stay Spooky Smiling Halloween Pumpkin For the Spooky Season of all Time and For Trick or Treat Game Hat
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Description: Stay Spooky Smiling Halloween Pumpkin For the Spooky Season of all Time and For Trick or Treat Game design for your apparel and other goods, please enjoy and make sure to visit my store for some anime and hip hop related designs, thank you :)

Tags: ghost, halloween, halloween costume gift, halloween gifts, horror
Retro Fall Vibes, Coquette Bow Pumpkin, Fall Smiling Ghost Hat
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Description: Vintage Pumpkin Ghost Fall Season Gifts

Tags: autumn, coquette bow pumpkin, fall, fall vibes, ghost pumpkin

Retro Fall Vibes, Coquette Bow Pumpkin, Fall Smiling Ghost Hat

by TuyrCanvas

$12 $19

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Antique framed portrait of a smiling pumpkin monster Hat

Description: He looks so proud of himself, like he just learned how to be scary but still wants a candy reward.

Tags: antique gold frame, children fall apparel, cozy autumn drawing, cute spooky illustration, hand drawn doodle

Antique framed portrait of a smiling pumpkin monster Hat

by Childish By Design

$12 $19

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Thanksgiving Pie Season Cute Smiling Pumpkin Slice Hat
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Description: A smiling slice of pumpkin pie sits above “Thanksgiving Pie Season” in warm autumn colors. A sweet choice for bakers, dessert lovers, and family feast celebrations.

Tags: baker, baking, cartoon, cute, dessert

Thanksgiving Pie Season Cute Smiling Pumpkin Slice Hat

by Dugong Japos

$12 $19

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Smiling Pumpkin Classic Pumpkin Eater Rhyme Hat
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Description: A cheerful orange jack o lantern sits above a short pumpkin themed nursery rhyme phrase. For pumpkin lovers and fans of playful nursery rhyme wordplay in autumn artwork.

Tags: autumn, autumn pumpkin illustration, carved pumpkin, fall harvest, folklore

Smiling Pumpkin Classic Pumpkin Eater Rhyme Hat

by Nooseeke

$12 $19

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COZY Season Cute Smiling Pumpkin Fall Autumn Women Hat
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Description: COZY Season Cute Smiling Pumpkin Fall Autumn Women

Tags: autumn, autumn vibes, cozy fall, cozy season, cute fall

COZY Season Cute Smiling Pumpkin Fall Autumn Women Hat

by Caliamo Lab

$12 $19

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Pumpkin Pancake Smiling Cartoon Fall Season Hat
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Description: This pumpkin pancake design captures the ultimate cozy autumn comfort with a delightful, smiling cartoon pumpkin lounging in a stack of golden pancakes. Surrounded by cinnamon, star anise, and maple syrup, this artwork is a sweet treat for any spice lover or gourmet foodie. It embodies the warm fall aesthetic and harvest season, perfect for Thanksgiving celebrations or simply enjoying a cozy breakfast. Celebrate your love for fall and delicious delights with this charming illustration.

Tags: autumn, autumn comfort, breakfast treat, cinnamon, cozy foodie

Pumpkin Pancake Smiling Cartoon Fall Season Hat

by Anaksingkong

$12 $19

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Cute Halloween Pumpkin Smiling Face Trick Or Treat Design Hat
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Description: Celebrate the spooky season with this adorable smiling halloween pumpkin. Perfect for kids and adults who love cute autumn vibes, this charming carved pumpkin design is a must-have for your next trick or treat adventure.

Tags: autumn, boo, carved pumpkin, cute, cute halloween

Cute Halloween Pumpkin Smiling Face Trick Or Treat Design Hat

by EmilyHargr

$12 $19

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Smiling Pumpkin Witch Hat Glasses Cute Halloween Character Hat

Description: A fun design built around smiling pumpkin witch perfect for fans of pumpkin witch hat witch hat glasses

Tags: cute halloween character, funny design, gift idea, glasses cute halloween, hat glasses cute

Smiling Pumpkin Witch Hat Glasses Cute Halloween Character Hat

by Neon Wings

$12 $19

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Halloween Pumpkin Smiling Hat
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Description: Spooky Halloween design for fans of creepy, scary and dark artwork. Perfect for Halloween, horror lovers, haunted nights, spooky parties, trick or treat and anyone who loves creepy Halloween vibes.

Tags: afraid, demon pumpkin, evil pumpkin, fear, halloween monster

Halloween Pumpkin Smiling Hat

by Instant Printing

$12 $19

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Happy Halloween Smiling Pumpkin With Sunglasses Hat
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Description: Celebrate Halloween in style with a smiling pumpkin wearing cool sunglasses and bold “Happy Halloween” text. Perfect for spooky season, horror fans, ghost and skeleton lovers, and pumpkin enthusiasts. Brings fun and festive autumn vibes to your fall celebrations.

Tags: funny, happy halloween, horror, retro, spooky

Happy Halloween Smiling Pumpkin With Sunglasses Hat

by Adam.myaw

$12 $19

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Cute Smiling Pumpkin Face Illustration Hat
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Description: Celebrate the autumn season with this cute and happy pumpkin face. Featuring a friendly smile, this simple design is perfect for Halloween decorations, seasonal gifts, and fall-themed apparel.

Tags: autumn, cute pumpkin, fall season, fall vibes, festive design

Cute Smiling Pumpkin Face Illustration Hat

by uborn

$12 $19

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Happy Halloween Cute Ghost Witch Black Cat Smiling Pumpkin Hat
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Description: Heartwarming storybook illustration of a friendly sheet ghost holding a glowing lantern beside a black kitten and an orange carved pumpkin under a crescent moon. A sweet holiday graphic made for elementary school teachers, children, and cozy autumn enthusiasts.

Tags: boys halloween, halloween, halloween cat, halloween costume, halloween for girls

Happy Halloween Cute Ghost Witch Black Cat Smiling Pumpkin Hat

by Blossom Bouquet Gallery

$12 $19

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Smiling Pumpkin ''Chillin' in my pumpkin'' Hat
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Description: A classic, smiling halloween pumpkin wearing a witch's hat and surrounded by autumn leaves and sparkles. The phrase ''CHILLLIN' IN MY PUMPKIN'' adds a playful touch. Perfect for fans of autumn traditions

Tags: autumn, autumn leaves, cute, kawaii, orange

Smiling Pumpkin ''Chillin' in my pumpkin'' Hat

by PechiStudio

$12 $19

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Teach Love Watch Grow Pumpkin Hat
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Description: This charming design features smiling pumpkins surrounded by colorful autumn leaves and the encouraging phrases "teach them," "love them," and "watch them grow." Perfect for celebrating the fall season, this design is ideal for families and teachers who cherish growth and love, complemented by the warm themes of harvest and thanksgiving.

Tags: autumn, cute, cute pumpkins, fall, family

Teach Love Watch Grow Pumpkin Hat

by luckybunnie268

$12 $19

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Pumpkin With Dental Braces Hat

Description: A cheerful cartoon pumpkin wearing dental braces surrounded by dental tools and autumn leaves. This fun vector illustration is perfect for orthodontists and dental professionals during the fall season.

Tags: autumn dental office, braces wearer apparel, bright orange gourd, cheerful facial expression, cute tooth graphic

Pumpkin With Dental Braces Hat

by Seasonal Whisper

$12 $19

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Happy Ghosts and Smiling Pumpkin Halloween Hat
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Description: Three cheerful ghosts float above a smiling pumpkin with bats, stars and curling vines. A cream Halloween Shirt design for fans of friendly ghosts and cute autumn artwork.

Tags: autumn, bats, fall season, friendly ghost, halloween party

Happy Ghosts and Smiling Pumpkin Halloween Hat

by Cosmic Void Collective

$12 $19

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Smiling Pumpkin Stack Halloween Social Club Humor Hat
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Description: Smiling Pumpkin Stack Halloween Social Club Humor

Tags: autumn, bat, candy, celebration, comedy

Smiling Pumpkin Stack Halloween Social Club Humor Hat

by Mistycoon

$12 $19

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Vintage Halloween Pumpkin Parade Three Marching Jack O Lanterns Hat
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Description: Three happy jack-o-lantern characters march together with rubber-hose cartoon limbs and a Halloween flag. A nostalgic vintage-style pumpkin parade design.

Tags: halloween, jack o lantern, marching, retro, retro cartoon
Cute Smiling Pumpkin Floral Bow Patchwork Fall Women Hat
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Description: Cute Smiling Pumpkin Floral Bow Patchwork Fall Women

Tags: autumn, autumn flowers, cottagecore, cozy fall, cute fall

Cute Smiling Pumpkin Floral Bow Patchwork Fall Women Hat

by Caliamo Lab

$12 $19

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You Wanna Piece Of Me Cute Pumpkin Pie Thanksgiving Hat

Description: Bring sweet autumnal humor to your holiday table with this cute pie layout. Featuring a smiling slice of spiced pumpkin pie topped with whipped cream, surrounded by falling autumn leaves and floating hearts, framed by the witty pun "You wanna piece of me?". A delightful selection for pastry chefs, bakers, and Thanksgiving dinner hosts.

Tags: autumn dessert layout, autumn pie layout, baking enthusiast piece, cozy autumn pastry, cute thanksgiving pastry

You Wanna Piece Of Me Cute Pumpkin Pie Thanksgiving Hat

by TYPE_STUDENT

$12 $19

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Witch Hat Black Cat over a Smiling Pumpkin Hat
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Description: A black cat in a witch hat crouches above a smiling pumpkin, combining familiar Halloween symbols in a playful feline scene. A thoughtful choice for cat lovers with an affection for witch hats and magical familiars.

Tags: black cat, black witch cat, cat, cat lover, cute feline familiar

Witch Hat Black Cat over a Smiling Pumpkin Hat

by Rooted Show

$12 $19

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Cute Halloween Ghost Witch Holding a Smiling Pumpkin Hat
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Description: Cute Halloween Ghost Witch Holding a Smiling Pumpkin

Tags: carloj1956, geek, horror, nerd, parody

Cute Halloween Ghost Witch Holding a Smiling Pumpkin Hat

by QuirkSketch

$12 $19

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Cute Halloween Ghost Wearing Beanie With Iced Coffee Art Hat
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Description: Stay cozy and spooky with this adorable autumn ghost design! Features a sweet white sheet ghost rocking an orange pom-pom knit beanie, holding an iced cold brew cup, and clutching a smiling carved pumpkin amidst fluttering bats. The cutest gift for iced coffee lovers and fall enthusiasts.

Tags: autumn coffee run, barista halloween top, cozy spooky season, cute beanie ghost, fall aesthetic spooky
Smiling Outside Empty Inside - Demotivational Pumpkin Hat
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Description: Meet the “Smiling on the Outside, Empty on the Inside” pumpkin—a brutally honest design that speaks to every introvert who’s just done. This pumpkin might look cheerful, but it’s flipping the bird and wearing that hollow smile for a reason. Perfect for anyone with a dark sense of humor, this design captures the feeling of masking the blahs with a grin. Let it be your go-to symbol for those days when the outside says "fine," but the inside is just... meh.

Tags: antisocial, dark humour, demotivational quote, empty inside, flipping the bird

Smiling Outside Empty Inside - Demotivational Pumpkin Hat

by Nemons

$12 $19

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Cute Pastel Patterned Ghosts Stars Halloween Hat

Description: Four adorable pastel ghosts decorated with bright polka dots, animal print, pumpkins, and daisies surrounded by colorful stars. A fantastic option for nail artists, hair stylists, and creative makers.

Tags: creative studio maker apparel, cute neon ghost lineup, floral pattern halloween ghost, hair stylist autumn style, halloween ghost boo

Cute Pastel Patterned Ghosts Stars Halloween Hat

by ArtMichalShop

$12 $19

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Smiling Jack O Lantern Man - Black Outlined Version Hat
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Description: This design features a spooky, smiling Jack o Lantern man! One additional version of this design, and many more original art designs, can be found in my TeePublic Shop :)

Tags: autumn, creepy, face, fall, halloween

Smiling Jack O Lantern Man - Black Outlined Version Hat

by CreatorNatTees

$12 $19

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Smiling Pumpkin Duo – Halloween Jack O’ Lanterns Hat
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Description: Two cheerful orange jack o’ lanterns with playful grins, bringing classic Halloween charm to spooky season.

Tags: cute halloween, f, halloween, jack o lantern, pumpkin duo

Smiling Pumpkin Duo – Halloween Jack O’ Lanterns Hat

by Sandy Pixel

$12 $19

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Hocus Pocus I Need Coffee To Focus Funny Fall Pumpkin Art Hat
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Description: Brew up some magical energy with this fun "Hocus Pocus I Need Coffee To Focus" design! Features iced pumpkin spice cups, hot whipped lattes with cinnamon sticks, autumn leaves, and smiling jack-o'-lanterns. A hilarious, relatable gift for coffee lovers, witches, and autumn enthusiasts.

Tags: autumn maple acorns, autumn morning coffee run, barista halloween gift, fall coffee addict, funny pumpkin spice latte
Cute Thanksgiving School Supplies Fall Harvest Friends Hat

Description: A cheerful Thanksgiving illustration featuring adorable cartoon school supplies celebrating the fall harvest season. Smiling crayons, colorful pencils, a festive pumpkin pie, and a charming autumn-themed character create a playful classroom-inspired scene. Decorated with pilgrim hats, cute turkey details, falling autumn leaves, and warm orange, yellow, and brown tones, the artwork captures a cozy Thanksgiving atmosphere. The kawaii cartoon style, expressive faces, and whimsical seasonal accents blend school spirit with autumn festivities, celebrating Thanksgiving traditions, classroom creativity, and the joyful charm of fall.

Tags: autumn leaves, autumn school supplies, cartoon school supplies, cute crayons, cute thanksgiving

Cute Thanksgiving School Supplies Fall Harvest Friends Hat

by Designs Of Doom

$12 $19

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