Funny Scarecrow Hats
Description: Copyright of all these designs belongs to the artist (Meghan Wallace or Doodle by Meg LLC) and may not be reproduced by anyone other than the artist for sale or any other commercial use. In accordance with Intellectual Property Policies my designs have been created using my own process and personal references. With that said if you like my style, are interested in commission design work, or interested in licensing my work feel free to email or DM me!
Description: A feathered straw hat hovers above a pink dress on a post while a startled boy in blue overalls sits on the grass. Another child watches beside a curious puppy, with leafy vines curling over a wooden fence. Premium quality pieces from Dashery powered by Teepublic carry this mischievous vintage comic scene onto soft cotton T-Shirts and glossy ceramic Mugs. Crisp black brushwork, sunny greens and oversized teal lettering sharpen the punchline, Not the Way It Looked.
Description: A vintage Halloween illustration featuring a creepy pumpkin-headed scarecrow surrounded by crows, pumpkins, autumn leaves, corn stalks, an antique lantern, and a weathered wooden fence. The distressed engraving style gives the artwork a rustic haunted farm atmosphere, perfect for Halloween lovers, spooky season fans, scarecrow enthusiasts, and vintage horror collectors.
Description: Looking rough but still making an effort. Depressed But Well Dressed combines a vintage scarecrow illustration with dry humor, turning an ordinary autumn icon into a clever statement about keeping up appearances even when life feels a little messy. Featuring a classic scarecrow in formal attire with a crow perched overhead, this design blends vintage illustration, rustic autumn charm, and minimalist typography into a bold graphic that's equal parts witty and timeless. The contrast between the polished outfit and the humorous phrase creates a design that instantly catches attention. Perfect for fans of sarcastic humor, dark comedy, vintage-inspired graphics, and clever wordplay.
Depressed but Well Dressed Funny Scarecrow Vintage Graphic Tee Hat
by arrivesatten
$12 $19
Description: Meet the ultimate company man. This funny scarecrow has been holding down the patch, rain or shine, making him the undisputed, long-standing Employee of the Month. He never complains, never takes a lunch break, and is absolute expert-level at scaring away the office drama (and the crows). Perfect for anyone who loves a clever work pun, autumn humor, or corporate sarcasm, this design makes a hilarious gift for hard workers, outstanding coworkers, or anyone who feels like they’ve been standing in the same spot at their job for way too long. Whether you are celebrating the fall season, Halloween, a workplace milestone, or just love a good dad joke, this tee is guaranteed to harvest some laughs!
Description: Celebrate the magic of fall with this cute Halloween scarecrow design! Featuring a charming scarecrow with a patchwork outfit, a straw hat, sunflowers, pumpkins, autumn leaves, a spooky jack-o'-lantern, black ravens, and a glowing harvest moon, this artwork blends rustic country charm with classic Halloween vibes. Perfect for autumn lovers, scarecrow fans, pumpkin enthusiasts, and anyone who enjoys cozy farmhouse style with a spooky seasonal twist. A festive design for fall season fans, harvest celebrations, and Halloween lovers who appreciate colorful rustic artwork.
Description: A detailed Halloween illustration featuring a stitched rag-doll scarecrow character carrying a glowing lantern and pumpkin lollipop, surrounded by jack-o'-lanterns, autumn leaves, a full moon, bats, and a spooky haunted house. The dramatic orange, red, and black palette gives the artwork a richly detailed creepy Halloween atmosphere.
Description: Get ready for the spooky season with this hilarious Halloween design! Featuring two quirky, dancing skeletons with glowing Jack-o'-lantern pumpkin heads, surrounded by playful hand-drawn stars. The artwork highlights the funny, distressed quote "TIS' THE SEASON TO BE PUMPKY", putting a spooky autumn twist on a classic holiday carol. Illustrated in a gritty, vintage sketch style, this design is perfect for Halloween parties, trick-or-treating, or anyone who loves autumn vibes and skeleton humor.
Tis-The-Season-To-Be-Pumpky-Funny-Dancing-Pumpkin-Skeletons-Halloween Hat
by trevor.323
$12 $19
Description: Protecting the best pumpkin in the patch, my original character Jack Straws worriedly sits astride it in the moonlight. This was one of my yearly Halloween pictures, and this character keeps popping up for things. I've even begun a story of his own. Let him be a part of your story and bring spooky Halloween fun any time of the year!
Description: Who needs real party guests when you have scarecrows? This hilarious vintage-style illustration features a dapper retro gentleman enjoying a cozy autumn tea party with a room full of scarecrows, complete with bold typography reading "SOLO PARTY". Crafted in iconic 1930s rubber-hose cartoon aesthetic, it makes a perfect witty gift for introverts, tea lovers, socially awkward humor fans, fall season, and retro streetwear lovers.
Solo Party Funny Introvert Scarecrow Tea Retro 1930s Cartoon Hat
by Yaymertch
$12 $19
