Sad Smiley Face Hats

Description: Sad Face is the new happy face

Description: DELIVERY SMILEY

Description: Smile Smile Smile Smile

Description: DELIVERY SMILEY

Description: The original teary eyed tongue waver from the Pink Man universe!

Description: The original teary eyed tongue waver

Description: HAPPY N SAD

Description: Mikey's knee pads

Description: A monochrome composition featuring the large white text "YOU" at the top, followed by two contrasting facial expressions: a happy face on the left and a sad face on the right. Below these are the large white letters "DECIDE".

Description: A yellow smiley face with black eyes and a black curved smile. A red blood splatter with a central bullet hole is depicted on the left eye area, with drips extending downwards.

Description: A smile can hide a lot. This distressed broken smiley face design blends dark humor with minimalist grunge aesthetics, creating the perfect statement piece for anyone who laughs through chaos and keeps going anyway. With its cracked vintage texture and emotionally charged vibe, this design fits perfectly into alt fashion, edgy streetwear, and dark aesthetic collections. Ideal for fans of grunge culture, ironic positivity, and expressive minimalist art.

Description: This eye-catching design features a cracked vintage smiley face that represents the powerful message: laughing on the outside, broken on the inside. Perfect for those who connect with deep emotions, dark humor, or mental health awareness. With a retro distressed style and bold typography, this design stands out on any apparel. Great for everyday wear, streetwear lovers, or anyone who appreciates meaningful and expressive art.

Description: Happy and sad faces Venn diagram you are here print

Description: A bright yellow circular sphere resembling a classic smiley face. The face has two black oval eyes and a curved black smile. A vibrant red splatter graphic is positioned across the left eye, with smaller red droplets radiating outwards. The background is black.

Description: Are you or someone you know and care about a victim of a Blue Control Player? Maybe you are that Blue Bully and just want to rub it in? Either way this "Smiley/Emoji" says it all without needing to say anything! If you LOVE Magic the Gathering, please check out my other Magic Themed designs by clicking on the ChristophZombie link above!

Description: A circular yellow smiley face with black eyes and a black smile is displayed centrally. Above the face, the text 'I CRY' is arching in yellow letters. Below the face, the text 'A LOT' is also in yellow, arching outwards. The background is black.

Description: This eye-catching design features a cracked vintage smiley face that represents the powerful message: laughing on the outside, broken on the inside. Perfect for those who connect with deep emotions, dark humor, or mental health awareness. With a retro distressed style and bold typography, this design stands out on any apparel. Great for everyday wear, streetwear lovers, or anyone who appreciates meaningful and expressive art.

Description: Hippy sad print inspired by a bad trip in the 90’s

Description: Now you can have the Not So Smiley Face for those rough days.

Description: A circular yellow emblem split vertically down the middle. The left side features a smiley face with blush marks and the text ':)', while the right side depicts a sad face with the text '('. The text 'SCHRÖDINGER'S' is curved above the circle in yellow.

Description: Groovy Melting Smile Face with lettering quote in 70s style. Stay groovy. Drippy Smiley Face.

Description: a design that represents the expression of a bipolar that is sad and happy at the same time

Description: too bad so sad - Smiley\sad face

Description: If you're happy and you know it clap...... Oh, wait. Never mind.....

Description: Who needs a weighted blanket when you’ve got...

Description: Graffiti Style Meh Face

Description: A retro-style graphic features a large yellow smiley face with black eyes and a black smile, superimposed on a sunset with horizontal stripes of red, orange, yellow, and teal. The text "ENJOY TODAY" is at the top, and "TOMORROW WILL BE WORSE" is at the bottom, both in white capital letters.

Description: A 'BE UNIQUE BY SHANIQUE' ORIGINAL! THANKS FOR STOPPING BY! :)

Description: my life is falling apart BUT i got cool sunglasses so it's fine

Description: a design that represents the expression of a bipolar that is sad and happy at the same time

Description: A retro-style cracked smiley face badge featuring the relatable quote "Laughing Outside Broken Inside." Perfect for fans of dark humor, grunge aesthetics, and emotional streetwear.

Description: This hand-drawn yellow smiley face with a single blue tear captures the perfect mix of dark humor, emotional realism, and simple expressive design. Created by MeltyShirts, this artwork blends a classic happy emoticon with a subtle, relatable twist—because sometimes you’re smiling on the outside and crying on the inside. Perfect for anyone who loves minimalist emotional art, relatable humor, alternative aesthetics, and soft irony. Great on t-shirts, hoodies, stickers, phone cases, mugs, notebooks, and more. Cute, honest, and instantly recognizable—wear your feelings without saying a word.

Description: Playful Abstract Emoji sad

Description: A centrally divided oval shape shows two distinct faces. The left side displays a happy emoticon with eyes represented by colons and a smile. The right side shows a sad emoticon with downturned eyes, a sorrowful mouth, and a " :((()" below it. The word "YOU" is above the oval, and "DECIDE" is below, both in bold, white capital letters.

Description: 1601

Description: This Bold-style Sad Clown illustration perfectly captures the feeling of using humor as a shield. Featuring a weeping clown holding a smiling mask, this design is ideal for fans of dark humor, sarcastic quotes, and Modern aesthetic streetwear. A relatable piece for anyone who says, "I make jokes so I don't cry."