Current offer expires in
-- H
-- M
-- S
Up to 35% Off Sitewide
Shop Now

Preppy Pumpkin Hats

Filter

Safe Search on hides explicit content. Safe Search off shows all results, including explicit content.
Preppy Pumpkin Patchwork Pumpkin Fall Coquette Shirt Hat
Main Tag:  

Description: Trendy patchwork pumpkin design with a bow, floral details, gingham accents, and cozy autumn style for fall lovers, pumpkin patch outfits, Thanksgiving looks, and preppy seasonal wardrobes.

Tags: autumn, bow pumpkin, coquette pumpkin, cozy autumn, cute fall

Preppy Pumpkin Patchwork Pumpkin Fall Coquette Shirt Hat

by trinitydreams

$12 $19

for
--
:
--
:
--

Preppy Jack O'Lantern Hat
Main Tag:  

Description: A trendy preppy Halloween design featuring a stylish jack-o'-lantern for spooky season lovers.

Tags: autumn, coquette, cute, fall, festive

Preppy Jack O'Lantern Hat

by la_ka_mo

$12 $19

for
--
:
--
:
--

Preppy Grandmillennial Pumpkin Halloween Hat

Description: Preppy Grandmillennial Pumpkin Halloween

Tags: prep

Preppy Grandmillennial Pumpkin Halloween Hat

by jenni nexus

$12 $19

for
--
:
--
:
--

Preppy Halloween Pumpkin Ghost Hat

Description: Preppy Halloween Pumpkin Ghost

Tags: funny halloween, girly halloween, halloween pumpkin, happy halloween, preppy halloween

Preppy Halloween Pumpkin Ghost Hat

by Haunted halow

$12 $19

for
--
:
--
:
--

Preppy Goose Pumpkin Coquette Halloween Hat
Main Tag:  

Description: Celebrate the cozy fall season with this adorable watercolor goose surrounded by pumpkins, blooming flowers, and soft pink stripes. Featuring a charming coquette aesthetic with elegant autumn details

Tags: coquette halloween, cute fall goose, floral pumpkin, goose pumpkin, pink halloween

Preppy Goose Pumpkin Coquette Halloween Hat

by jollydoomworld

$12 $19

for
--
:
--
:
--

Preppy Spooky Pumpkin Hat
Main Tag:  

Description: Preppy Spooky Pumpkin

Tags: aesthetic, autumn, autumn vibes, jack o lantern, pastel goth

Preppy Spooky Pumpkin Hat

by Sour Lemon

$12 $19

for
--
:
--
:
--

Preppy Floral Fall Pumpkin Halloween Hat

Description: Preppy Floral Fall Pumpkin Halloween

Tags: autumn, fall, floral, halloween, preppy

Preppy Floral Fall Pumpkin Halloween Hat

by Pretty glamor

$12 $19

for
--
:
--
:
--

Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween,Retro Pumpkin Patch Hat

Description: Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween,Retro Pumpkin Patch , Vintage Fall, Farm Fresh Pumpkin

Tags: cute halloween, farm fresh, funny halloween, girly halloween, halloween
Pumpkin Pie and Family Drama, Funny Thanksgiving Dinner Quote, Cute Preppy Turkey Day Humor, Sarcastic Family Gathering, Retro Fall Holiday Aesthetic Hat
Main Tag:  

Description: Pumpkin Pie and Family Drama, Funny Thanksgiving Dinner Quote, Cute Preppy Turkey Day Humor, Sarcastic Family Gathering, Retro Fall Holiday Aesthetic

Tags: pumpkin pie and family drama, funny thanksgiving, thanksgiving humor, family drama, happy thanksgiving
Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween,Retro Pumpkin Patch Hat

Description: Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween,Retro Pumpkin Patch , Vintage Fall, Farm Fresh Pumpkin

Tags: cute halloween, farm fresh, funny halloween, girly halloween, halloween
Preppy Patchwork Thankful Pumpkin Turkey Bow Thanksgiving Family Matching Hat

Description: Preppy Patchwork Thankful Pumpkin Turkey Bow Thanksgiving Family Matching

Tags: bow, pumpkin, thankful, thanksgiving, turkey
Pumpkin Teacher Preppy Fall In Love With Learning Cozy Autumn Hat
Main Tag:  

Description: Pumpkin teacher design with a cute retro autumn cartoon and learning text.

Tags: autumn cartoon, back to school, education, fall season, pumpkin art

Pumpkin Teacher Preppy Fall In Love With Learning Cozy Autumn Hat

by lucidglitch

$12 $19

for
-- days
--
:
--
:
--

Boho Fall Shirt Preppy Grandmillennial Pumpkin Coquette Bow Floral Hat

Description: A chic fall design blending boho florals with grandmillennial charm. Perfect for autumn lovers, cozy vibes, and quirky fashion fans.

Tags: autumn floral bow, boho fall, boho pumpkin, coquette bow, coquette pumpkin
Preppy Coquette Camo Pumpkin, Fall Bow, Cute Autumn Pumpkin, Retro Fall Gift Hat
Main Tag:  

Description: Preppy Coquette Camo Pumpkin, Fall Bow, Cute Autumn Pumpkin, Retro Fall Gift

Tags: aesthetic, autumn, camo pumpkin, camouflage pumpkin, coquette pumpkin
Boho Pumpkin Preppy Fall Cute Coquette Autumn Thanksgiving Hat

Description: Boho Pumpkin Preppy Fall Cute Coquette Autumn Thanksgiving

Tags: autumn colors, autumn fall, autumn nature, boho floral, coquette aesthetic

Boho Pumpkin Preppy Fall Cute Coquette Autumn Thanksgiving Hat

by catador design

$12 $19

for
--
:
--
:
--

Retro Raccoon Fall , Sassy Autumn Tee, Funny Trash Panda Pumpkin Latte , Preppy Fall Graphic , Leaves Fall I Don't Hat
Main Tag:  

Description: Retro Raccoon Fall , Sassy Autumn Tee, Funny Trash Panda Pumpkin Latte , Preppy Fall Graphic , Leaves Fall I Don't

Tags: autumn, caffeine, coffee, coffee drinks, cup of coffee
Preppy Thankful Pumpkin Hat

Description: Preppy Thankful Pumpkin, Retro Christian Fall, Coquette Thanksgiving, Pumpkin Bible, Religious Fall Doodle, Leopard

Tags: animal, cat, cat dad, cat lover, coquette thanksgiving

Preppy Thankful Pumpkin Hat

by platypeach.studios

$12 $19

for
--
:
--
:
--

Preppy Thankful Pumpkin Hat

Description: Preppy Thankful Pumpkin, Retro Christian Fall, Coquette Thanksgiving, Pumpkin Bible, Religious Fall Doodle, Leopard

Tags: animal, animals, coquette thanksgiving, cute, funny

Preppy Thankful Pumpkin Hat

by platypeach.studios

$12 $19

for
--
:
--
:
--

Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween Hat
Main Tag:  

Description: Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween

Tags: cute halloween, funny halloween, girly halloween, halloween, halloween for girls

Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween Hat

by Devils Duo Podcast

$12 $19

for
--
:
--
:
--

Retro Pumpkin Patch Hat
Main Tag:  

Description: Retro Pumpkin Patch, Preppy Autumn, Trendy Fall, Vintage Autumn, Distressed Fall, Farm Fresh, Funny Pumpkin

Tags: animal, cat, cat christmas, cat dad, cat lover

Retro Pumpkin Patch Hat

by Bravo Tattoo Team

$12 $19

for
--
:
--
:
--

Leopard Checkered Bow Pumpkin Trio Preppy Fall Hat

Description: A trio of textured, hand-painted-style pumpkins — checkered, leopard print, and polka dot, each tied with a bow — a preppy coquette take on classic fall imagery.

Tags: autumn preppy design, checkered pumpkin art, coquette autumn design, coquette fall design, fall bow pumpkin art

Leopard Checkered Bow Pumpkin Trio Preppy Fall Hat

by Jim fako

$12 $19

for
--
:
--
:
--

Cute Preppy Floral Patchwork Ghost Halloween Boo Pumpkin Hat

Description: Cute Preppy Floral Patchwork Ghost Halloween Boo Pumpkin

Tags: ghost, halloween, patchwork, pumpkin
Striped Preppy Fall Pumpkin Bow Hat
Main Tag:  

Description: Welcome the cozy season with this Striped Preppy Fall Pumpkin Bow design. Featuring a charming pumpkin decorated with classic stripes and a trendy bow, this artwork combines preppy style, coquette aesthetics, and autumn charm. Perfect for pumpkin patch visits, fall festivals, Thanksgiving gatherings, and anyone who loves cute seasonal fashion. Looks great on t-shirts, hoodies, stickers, mugs, tote bags, and makes a thoughtful gift for fall lovers.

Tags: coquette pumpkin, preppy pumpkin, pumpkin bow, striped preppy fall pumpkin bow, striped pumpkin

Striped Preppy Fall Pumpkin Bow Hat

by Dtiys

$12 $19

for
--
:
--
:
--

Boho Pumpkin Preppy Fall Autumn Vibes Thanksgiving Hat

Description: Boho Pumpkin Preppy Fall Autumn Vibes Thanksgiving

Tags: autumn, fall, pumpkin, thanksgiving

Boho Pumpkin Preppy Fall Autumn Vibes Thanksgiving Hat

by Super Kens

$12 $19

for
--
:
--
:
--

Preppy Fall Polka Dots, Coquette Floral Autumn, Retro Fall Pumpkin, Thanksgiving, Pumpkin Spice, Leopard, Pumpkin Bow Hat
Main Tag:  

Description: Preppy Fall Polka Dots, Coquette Floral Autumn, Retro Fall Pumpkin, Thanksgiving, Pumpkin Spice, Leopard, Pumpkin Bow

Tags: aesthetic, autumn, bow, coquette, cozy vibes
Fall Coffee Pumpkin Spice Autumn Drinks Preppy Halloween Cute Caffeinated Hat
Main Tag:  

Description: Celebrate cozy season with Fall Coffee, Pumpkin Spice & Autumn Drinks! This festive design features whipped coffee drinks, pumpkins, autumn leaves, cinnamon, coffee beans, and cute Sweater Weather and Autumn Leaves, Coffee Please lettering. Perfect for coffee lovers and preppy Halloween fans.

Tags: autumn coffee, autumn leaves, autumn leaves and coffee please, autumn season, coffee please
Spooky It's Vibes Cute Ghost Pumpkin Cauldron Preppy Halloween Hat
Main Tag:  

Description: Get into the ultimate autumn spirit with this vibrant "Spooky It's Vibes" Halloween design! Perfect for fans of preppy, colorful holiday aesthetics, this graphic features a cute little ghost wearing a cozy orange knit beanie. The ghost is holding a classic jack-o'-lantern candy bucket filled with sweet treats in one hand and a skull-topped magic staff in the other. Set against a distressed vertical striped background, the scene is complete with carved pumpkins, flying bats, dangling spiders, and a bubbling green potion cauldron on an open fire. With its bold orange, green, and purple typography, this design delivers the perfect blend of cozy fall vibes and spooky fun. Ideal for trick-or-treating, autumn pumpkin patch visits, or everyday wea

Tags: autumn pumpkin, candy bucket, colorful spooky, cozy fall, cute ghost halloween
Preppy Pumpkin Leopard Hat
Main Tag:  

Description: Preppy Pumpkin Leopard, Girly Pumpkin, Trendy Autumn, Fall Pumpkin, Funny Girly, Trendy Thanksgiving

Tags: autumn, dad, fall, fall pumpkin, father

Preppy Pumpkin Leopard Hat

by BRAND ZMLAWI

$12 $19

for
--
:
--
:
--

Just Here For The Pie And Family Drama Hat
Main Tag:  

Description: Just Here For The Pie And Family Drama, Funny Preppy, Humor Turkey, Thanksgiving Family, Pumpkin Pie, Family Drama, Thanksgiving Dinner

Tags: back to school, family drama, halloween, horror, humor turkey

Just Here For The Pie And Family Drama Hat

by Von Carpe

$12 $19

for
--
:
--
:
--

No Kings October 2026 Protest Vote Preppy Pumpkin Pink Hat
Main Tag:  

Description: No Kings October 2026 Protest Vote Preppy Pumpkin Pink

Tags: 2026, funny, halloween, kings, october

No Kings October 2026 Protest Vote Preppy Pumpkin Pink Hat

by Curves and Curls

$12 $19

for
--
:
--
:
--

Trendy Black Cat Preppy Floral Halloween Spooky Season Design Hat
Main Tag:  

Description: Celebrate spooky season with this adorable black cat design featuring preppy floral details and cozy autumn charm. Perfect for cat lovers, Halloween fans, and anyone who enjoys cute fall aesthetics with a feminine touch. Great for pumpkin patch visits, Halloween parties, fall festivals, and all your favorite autumn adventures.

Tags: autumn aesthetic, cat lover, coquette fall, cozy autumn, cute black cat
Preppy Spooky Checkered Haunted House Pink Pumpkin Spooky Hat

Description: Preppy Spooky Checkered Haunted House Pink Pumpkin Spooky

Tags: fall, halloween, humor, pumpkin, retro
Pretty in Pumpkin Latte Hat

Description: Satisfy your need for caffeine AND your addiction to Autumn with this bright beverage-inspired graphic!

Tags: barista coffee lover gift idea, basic bitch witch preppy, coffee is always a good idea, drink beverage coffee sip, every day is halloween

Pretty in Pumpkin Latte Hat

by Jan Grackle

$12 $19

for
--
:
--
:
--

Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween,Retro Pumpkin Patch Hat
Main Tag:  

Description: Pumpkin Patch , Preppy Fall Pumpkin, Girly Halloween,Retro Pumpkin Patch , Vintage Fall, Farm Fresh Pumpkin

Tags: boys halloween, cute halloween, farm fresh, funny halloween, girly halloween
Preppy Fall Pumpkin Football Game Day Leopard Checkered Bow Hat

Description: Celebrate football season with a stylish fall design featuring footballs, leopard print, buffalo plaid, a bold bow and autumn-inspired details. A fun coquette-style graphic for game day and football fans.

Tags: autumn, bow, checkered, fall, festive

Preppy Fall Pumpkin Football Game Day Leopard Checkered Bow Hat

by Okay Odd Studio

$12 $19

for
--
:
--
:
--

Preppy Pumpkin Trio Leopard Checkered Boho Fall Autumn Hat
Main Tag:  

Description: A trendy fall design featuring a trio of pumpkins decorated with leopard, checkered, and boho-inspired patterns. Perfect for pumpkin lovers, autumn enthusiasts, and anyone who enjoys preppy seasonal aesthetics. A playful mix of cozy fall charm and stylish patterns for pumpkin season.

Tags: autumn pumpkin, autumn vibes, boho autumn, boho pumpkin, checkered fall

Similar Designs

Cart Preview (0)

Adult Apparel

Kids Apparel

Home Goods