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Sassy Smile Pins

Browse our collection of 970 Sassy Smile Pins . Most designs are also available on T-Shirts, Tank Tops, Racerbacks, Sweatshirts, Hoodies and other items. Designed and printed in the USA. 100% Satisfaction Guaranteed.

Celebrate The Woman In Your Life With These Empowering Gifts

These Positive Gifts Are Sure To Make You Smile

Smile Through The Woes Of Aging With Our Growing Pain Items

Sassy Sassy Pin Funny Memes Animals Cats Sarcasm Feminism Funny Pin Puns Witches Food Retro Occult Parody Sassy Pins Halloween Introvert Jokes Nerds

Don't you just love it when someone gives you the cutest smile? Yeah, Ditto.

Sassy Raccoon Pin

Sassy Raccoon Pin

Show off your fierce, sassy inner trash with this funny, Sassy Raccoon design! Perfect for raccoon humor, being sassy, trashy, and telling people to back off!

Don't Tell Me To Smile Dino Pin

Don't Tell Me To Smile Dino Pin

This sassy feminist dinosaur design reads, Don't Tell Me To Smile and features an angry raptor ready to tear the head off of any misogynist getting in her way! Use this dino design to let everyone know that they better think twice before telling you to smile!

Trashy and Sassy Pin

Trashy and Sassy Pin

Just because you indulge in garbage doesn't mean you can't be glamorous. Inspired by photos of opossums wearing pink hair bows, this adorable pin is perfect for any fans of the strange marsupial!

Wordle Pixel Smile Pin

Wordle Pixel Smile Pin

You guessed it! Show off your smile of satisfaction of guessing the Wordle word of the day with this Wordle pixel smile parody! Perfect for loving puzzle games and word guessing.

Existing Is Hard Rainbow Smile Pin

Existing Is Hard Rainbow Smile Pin

Existing is hard! Show off your honesty about life's challenges and circumstances, it's brutal out here! Perfect for feeling overwhelmed with existential thoughts and trying to find the rainbow in the rain.

Existing Is Hard Rainbow Smile Pin

Existing Is Hard Rainbow Smile Pin

Existing is hard! Show off your honesty about life's challenges and circumstances, it's brutal out here! Perfect for feeling overwhelmed with existential thoughts and trying to find the rainbow in the rain.

Don't Tell Me To Smile Shark Pin

Don't Tell Me To Smile Shark Pin

Show off your love of sharks and your hatred of the patriarchy with this shark lover's, shark week inspired, "Don't Tell Me To Smile" necklace! Now show off those razor sharp teeth and tell those jerks to f*** off!

College Educated Sassy Feminist Mom Pin

College Educated Sassy Feminist Mom Pin

College Educated Sassy Feminist Mom. Show you're a proud mom and a proud feminist with this sassy design.

Don't Tell Me to Smile Shark Pin

Don't Tell Me to Smile Shark Pin

Show off your love of sharks and your hatred of the patriarchy with this shark lover's, shark week inspired, "Don't Tell Me To Smile" necklace! Now show off those razor sharp teeth and tell those jerks to f*** off!

Current Mood Sassy Bernie Sanders Pin

Current Mood Sassy Bernie Sanders Pin

Show off your current mood with this sassy, cozy, Bernie Sanders shirt! Bernie is always a mood why not show it off with this funny and sassy pin of Bernie sitting at the 46th US presidential Inauguration!

Don't Tell Me To Smile (Queen Of Swords Tarot) Pin

Don't Tell Me To Smile (Queen Of Swords Tarot) Pin

Ah, you have drawn the Queen of Swords- aka "Don't tell me to smile". It's not difficult to tell what this card's about! Set some clear boundaries and keep the message direct with this funny parody of the Rider Waite Smith Tarot card, the Queen of Swords!

Why Don't You Give Me a Smile Pin

Why Don't You Give Me a Smile Pin

Next time someone demands you or asks you that question, throw it back at them and give 'em a taste of their own medicine. Make it as awkward and uncomfortable as possible.

Booties Make Me Smile Pin

Booties Make Me Smile Pin

Booties are one of the most innocent yet cheeky (pun intended) things to exist. Almost everyone can appreciate and get a laugh out of it. Plus, we all have one!

My Students Make Me Smile Pin

My Students Make Me Smile Pin

One of the most fulfilling feelings in the world is being a teacher living with a purpose and passion for their students.

I Felt Sad Butt You Made Me Smile Pin

I Felt Sad Butt You Made Me Smile Pin

I felt sad BUTT you made me smile! Show off how happy your booty is with this cute and funny, flirty, smiley face booty design.

Yo Bro Who Got You Smiling Like That Fall & Pumpkin Spice Pin

Yo Bro Who Got You Smiling Like That Fall & Pumpkin Spice Pin

Who got me smiling like this? Pumpkins, spiced lattes, leaves, halloween, apple picking, fall fashion, fall colors- honestly, all of it. Feel the joy of autumn with this cute design!

Don't Be An Asshole Winking Smiley Pin

Don't Be An Asshole Winking Smiley Pin

Hey man, just be kind! Show off your sassy smile for kindness with this, "Don't Be An Asshole" retro, winking, smiley face design!

Medusuck My Dick Pin

Medusuck My Dick Pin

Oh, you want Medusa to smile, well then Medusuck My Dick! This sassy gorgon of greek mythology gets a little NSFW with those "snakes" on her head.

Please Leave Me Alone Smiley Pin

Please Leave Me Alone Smiley Pin

Please leave me alone. :) Thank you! Show that you'd rather be left alone with this sassy smiley face design.

I Don't Want To Look "Approachable" Pin

I Don't Want To Look "Approachable" Pin

Don't tell me to smile, don't tell me what to wear, don't tell me my makeup makes me less "approachable". Wear goth shit and don't give a F*** about how others perceive you with this unamused goth smiley face.

Sugar, Spice, And Under No Obligation To Be Nice. Pin

Sugar, Spice, And Under No Obligation To Be Nice. Pin

Sugar, spice, and under no obligation to be nice - these are the things that girls are made of! Show off your sassy, fierce feminist, girl power attitude with this parody design.

Just Another Day In The Simulation Smiley Pin

Just Another Day In The Simulation Smiley Pin

Is reality actually a simulation? Whatever it is, it's rough! Grin and bear it with this sassy, "Just Another Day In The Simulation" smiley design!

Help Me Smily Face Pin

Help Me Smily Face Pin

Help me. Ask for help with a smile with this somewhat creepy, funny design.

You're Weird I Like You Pin

You're Weird I Like You Pin

Being called out by someone as weird as you is one of the best compliments in the world. It's rare to connect on a derpy level so let that person know with this wholesome melting smile design.

Be Kind Flower Power Smileys Pin

Be Kind Flower Power Smileys Pin

Be kind and bloom! Show off your flower power of care with this fun, retro, groovy, floral smileys design.

Doing My Little Tasks While The World Crumbles Pin

Doing My Little Tasks While The World Crumbles Pin

Everything is fine! I'll just smile through doing my little tasks while the world crumbles further into a capitalist hellscape!

Woke Up And Chose To Be A Menace Pin

Woke Up And Chose To Be A Menace Pin

Give people a warning that today, you chose to be a menace after waking up. It's the most courteous thing you'll be doing for them.

Woke Up And Chose To Be A Menace Pin

Woke Up And Chose To Be A Menace Pin

Give people a warning that today, you chose to be a menace after waking up. It's the most courteous thing you'll be doing for them.

You Can't Live Without Me Pin

You Can't Live Without Me Pin

Let's face it, we all need the sun in order to survive, because who else will provide us all the vitamin D and kisses on our skin?

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