Crying Hats
Description: A humorous and slightly melancholy holiday design featuring two raccoons wearing festive Santa hats. The larger raccoon is in the foreground, crying with visible tears. Above them, text reads 'MERRIER CHRISTMAS TO SOME, SADNESS FOR THE REST.' The raccoons have striped tails and are colored in shades of grey and black with white accents.
Merrier Christmas To Some, Sadness For The Rest Crying Raccoons Hat
by STUDIO DESIGN PESSO
$12 $19
Description: A distressed woman crouches under a messy desk, covering her face with her hands. Papers are scattered around, and a bottle labeled "FIZZY POP" lies on its side. The computer monitor displays "ERROR... SYSTEM FAIL". The scene is bordered by orange and yellow stripes.
Woman Crying Under Desk "ERROR... SYSTEM FAIL" with "FIZZY POP" Hat
by GRAPHIC CHARCOAL DARK
$12 $19
Crying Stickman Ow Ow - Funny Pain Stick Man Meme Humor Hat
by eighty three
$12 $19
Description: A crying pink love letter envelope with wings flying on a colorful splash background. A funny and dramatic kawaii illustration for anime lovers and romantic humor fans.
Notice Me Please Cute Crying Pink Love Letter Mascot Hat
by angsabiru design
$12 $19
Description: I Don't Care How Many Girls Make Him Laugh Funny Quote I Don't Care How Many Girls Make Him Laugh Joke It's entertaining to wear this design every day. Are you looking for a matching design? Then you should buy this outstanding design! Ideal for those who love being wild, cool, and amusing, this eye-catching design makes a wonderful gift for your mother, aunt, grandmother, sister, or anybody else you care about.
Description: Tears of Inflation: The Crying Hundred-Dollar Founding Father Tears of Inflation by Puff Sumo. Benjamin Franklin, the face on the hundred dollar bill, finally breaks down: a single dollar-sign tear rolls down his cheek in this hand-engraved style portrait. It's the perfect satire for anyone feeling the squeeze of rising prices, grocery bills, rent hikes, and a paycheck that stretches less every month. Cost of living crisis humor, economic anxiety, and finance memes all collide in one weeping founding father. Bold black linework on cream tones, inspired by classic banknote engraving and vintage woodcut portraits. A conversation starter for savers, realists, and anyone who has said prices are insane.
Tears of Inflation: The Crying Hundred-Dollar Founding Father Hat
by Puff Sumo
$12 $19
Employees Must Stop Crying Before Work, Funny Retro Design Hat
by Contrast Gallery
$12 $19
Description: Crown the family pun master with this hilarious "Dad Joke Champion" vintage graphic. Featuring a highly detailed, hand-drawn crying laughing emoji, bold retro block lettering, and a weathered "CHAMPION" ribbon banner, it’s the perfect witty apparel choice for Father's Day, family gatherings, or his birthday.