Ironic Optimism Caps

119 items

Pretend It's OK Baseball Cap

mushroomblue

$20.15

~~$25.19~~ (20% off)

Optimism Pending Dad Hat

OptimismPending

$19.62

~~$23.09~~ (15% off)

Resist Optimism Baseball Cap

DontGiveaShirt

$20.15

~~$25.19~~ (20% off)

I'm Fine Baseball Cap

Not Diome

$20.15

~~$25.19~~ (20% off)

Sorry for party rocking Dad Hat

Not Diome

$21.41

~~$25.19~~ (15% off)

Glass half full or half empty? Dad Hat

dgsein

$23.19

~~$27.29~~ (15% off)

Polite Pessimist Collection Baseball Cap

Schrodinger's Clothing

$18.47

~~$23.09~~ (20% off)

Silver lining: Things could suck more | Ironically optimistic Baseball Cap

ThingsOnTees

$20.15

~~$25.19~~ (20% off)

Silver lining: Things could suck more | Ironically optimistic Dad Hat

ThingsOnTees

$21.41

~~$25.19~~ (15% off)

OPTYMISTIC PRIME Baseball Cap

ViralVisionsCreating

$21.15

~~$26.45~~ (20% off)

Stay Positive Alligator Funny Dark Humor Graphic Baseball Cap

Amazing Graphics

$21.83

~~$27.29~~ (20% off)

Stay Positive Cat Riding a Great White Shark Dad Hat

TeeARTHY

$21.41

~~$25.19~~ (15% off)

This Little Light Of Mine, I'm Gonna Let It Shine Dumpster Fire Sarcasm Humor Dad Hat

HumansStuck12

$32.11

~~$37.78~~ (15% off)

Hidden Existential Dread Typography for When Everything is Fine! Dad Hat

kierkegaard

$21.41

~~$25.19~~ (15% off)

Anti-inspirational Throw Pillow Baseball Cap

kierkegaard

$20.15

~~$25.19~~ (20% off)

Happy Days Are Just A Phase in Lavender Dad Hat

Pink Ribbon

$21.05

~~$24.77~~ (15% off)

Retro Atomic Optimism Sticker – Cozy Apocalypse Survival Humor Dad Hat

JacobKAurumhead

$21.41

~~$25.19~~ (15% off)

Freaking Optimist | Funny Optimism | Ironic Pessimist Dad Hat

MadamBullmoose

$21.41

~~$25.19~~ (15% off)

All too well, Positive word, Optimism, Humor Baseball Cap

cyhdesign

$20.15

~~$25.19~~ (20% off)

All too well, Positive word, Optimism, Humor Dad Hat

cyhdesign

$21.41

~~$25.19~~ (15% off)

All too well, Positive word, Optimism, Humor Baseball Cap

cyhdesign

$20.15

~~$25.19~~ (20% off)

All too well, Positive word, Optimism, Humor Baseball Cap

cyhdesign

$20.15

~~$25.19~~ (20% off)

Hang In There - It Gets Worse | Retro Bomb Cartoon Dad Hat

PrintItStudio

$19.62

~~$23.09~~ (15% off)

Optimism is disappointment, sarcastic, cynical humor, Funnyfits70, retro, vintage, meme, funny, humor Dad Hat

FunnyFits70

$21.32

~~$25.08~~ (15% off)

Anxiety Thumbs Up wh Baseball Cap

pehhappy

$19.31

~~$24.14~~ (20% off)

Good News… Just Kidding Cheerful Skeleton Dark Humor Art Baseball Cap

FlyShop1

$20.15

~~$25.19~~ (20% off)

I'M FINE Dumpster Fire - Ironic Humor Meme Dad Hat

ArtPandax

$19.62

~~$23.09~~ (15% off)

Optimism is a Design Choice Baseball Cap

Grand Illusions

$20.15

~~$25.19~~ (20% off)

Optimism Meets Reality – Tornado Silver Lining Humor Baseball Cap

The Junto Shop

$20.15

~~$25.19~~ (20% off)

Delusionally Optimistic And Thriving Funny Positive Quote Baseball Cap

WakeNBake-Tees

$21.83

~~$27.29~~ (20% off)

POSITIVE, my friend… POSITIVE! Dad Hat

Frédéric G •

$19.62

~~$23.09~~ (15% off)

It's Always Sunny - white Baseball Cap

VasInd

$21.83

~~$27.29~~ (20% off)

Apocalypse, But Make It Cozy Dad Hat

0dirtyrice0

$21.41

~~$25.19~~ (15% off)

It's Always Sunny Baseball Cap

VasInd

$21.83

~~$27.29~~ (20% off)

Retro Atomic Camping Survival Illustration Dad Hat

FireScreen

$19.62

~~$23.09~~ (15% off)

Goat Titanic Selfie Funny Disaster Humor Meme Gift Baseball Cap

Say It With Ink

$20.15

~~$25.19~~ (20% off)

Delulu Is The Solulu Funny Star Eyed Emoji Meme Baseball Cap

lowbatterydept

$20.15

~~$25.19~~ (20% off)

Molten Comfort Baseball Cap

0dirtyrice0

$20.15

~~$25.19~~ (20% off)

Not Praying for Good Things Anymore Just Make the Bad Stuff Stop | Snarky Dystopian Humor Dad Hat

Ignorant-Artist

$21.41

~~$25.19~~ (15% off)

Item preview, Existential Optimism Cat - Funny Dark Humor designed and sold by A-T-H.

Existential Optimism Cat - Funny Dark Humor Baseball Cap

A-T-H

$20.15

~~$25.19~~ (20% off)

Optimistic Approach to Pessimism – Funny Introvert or Overthinker Quote Dad Hat

SnarkSharks

$21.41

~~$25.19~~ (15% off)

Hang in there, Hang in there it gets worse, dumpster fire, funnyfits70, Humor, Funny, retro, vintages, funny quotes, animal humor, Baseball Cap

FunnyFits70

$20.06

~~$25.08~~ (20% off)

Hang in there, Hang in there it gets worse, dumpster fire, funnyfits70, Humor, Funny, retro, vintages, funny quotes, animal humor, Dad Hat

Optimism With Backup Plans Funny Cat Motivation Meme Dad Hat

OptimismPending

$19.62

~~$23.09~~ (15% off)

Hang In There It Gets Worse Dark Humor Sarcasm Skeleton Pessimist Dad Hat

HumansStuck12

$32.11

~~$37.78~~ (15% off)

Retro Atomic Factory Collapse Illustration Dad Hat

FireScreen

$19.62

~~$23.09~~ (15% off)

Ironic Sunny Days Camel - Funny Rain and Sarcastic Weather Humor Baseball Cap

SoulPT

$20.15

~~$25.19~~ (20% off)

Hang On Tight – Failure – Midnight Breakdown Dad Hat

buglevel

$21.41

~~$25.19~~ (15% off)

Vintage Advertising Post Apocalyptic Slogan Dad Hat

Mr-AShop

$26.58

~~$31.28~~ (15% off)

Nothing matters. Let's proceed. Dad Hat

buglevel

$21.41

~~$25.19~~ (15% off)

Hope Was a Mistake – Gothic Skull Dark Humor Nihilism Macabre Horror Occult Design Baseball Cap

Alchemy Forge

$20.15

~~$25.19~~ (20% off)

Motivation Found Baseball Cap

WonderBox

$20.15

~~$25.19~~ (20% off)

Death the gardener and her watering can of hope Dad Hat

Stickers à gogo

$19.62

~~$23.09~~ (15% off)

All Clear Baseball Cap

It's Heritage Hoss

$19.98

~~$24.98~~ (20% off)

Sarcastic Retro Astronaut Follow Your Dreams Irony Dad Hat

RareVisuals

$21.41

~~$25.19~~ (15% off)

Never Better - Thumbs Up Crash Scene Dad Hat

Automotive Art by Greg

$19.62

~~$23.09~~ (15% off)

Hang On Tight – Failure – Toxic Sunshine Baseball Cap

buglevel

$20.15

~~$25.19~~ (20% off)

Everything Is Functioning Baseball Cap

It's Heritage Hoss

$19.98

~~$24.98~~ (20% off)

Ziggy Optimism Cartoon Shirt - Funny Silver Lining Comic Tee 2025 Baseball Cap

"Hopeful Bird in Chaotic Weather" Baseball Cap

Elisant

$20.15

~~$25.19~~ (20% off)

Nothing Bad Can Happen – Trump Tylenol Quote Design Baseball Cap

ChickenFund

$20.15

~~$25.19~~ (20% off)

This Is Fine – Smiling Dumpster Fire Baseball Cap

Full Throttle Alchemist

$20.15

~~$25.19~~ (20% off)

Hang in there it gets worse cheerful sun irony Dad Hat

HumansStuck12

$32.11

~~$37.78~~ (15% off)

2026 Will Be My Year – Sarcastic Optimism Design Dad Hat

Redgiant87x

$21.41

~~$25.19~~ (15% off)

The Future Is So Bright – Kawaii Bear Dark Humor Art Dad Hat

Cheeky Companions

$21.41

~~$25.19~~ (15% off)

Stay Positive House on Fire – Dark Humor Ironic Meme Design Baseball Cap

InkwildStudio

$20.15

~~$25.19~~ (20% off)

Keep Rolling – Funny Volcano Adventure Cartoon Baseball Cap

mostafa gebril ⭐⭐⭐⭐⭐

$19.31

~~$24.14~~ (20% off)

Item preview, Delulu Mindset | Fantasy Over Reality | Viral Slang | Soft Aesthetic | Gen Z Manifestation | Dreamer Energy | Ironic Motivation | Vibe Shift designed and sold by LOWKEY LEGENDARY APPAREL™.

LOWKEY LEGENDARY APPAREL™

$20.15

~~$25.19~~ (20% off)

Item preview, "Stay Pawsitive, We’re All Gonna Die" – Dark Humor Cat Pun Design designed and sold by A-T-H.

"Stay Pawsitive, We’re All Gonna Die" – Dark Humor Cat Pun Design Baseball Cap

A-T-H

$20.15

~~$25.19~~ (20% off)

Nothing Bad Can Happen – Trump Tylenol Quote Design Neon Baseball Cap

ChickenFund

$20.15

~~$25.19~~ (20% off)

Not Fully Aligned Today Funny Mental Health Typography Dad Hat

DuckOddity

$21.77

~~$25.61~~ (15% off)

Delulu Is The Solulu - Cute Pastel Dreamy Smiley Face Gen Z Meme Dad Hat

Arts Paradise

$21.41

~~$25.19~~ (15% off)

Smile Through the Existential Dread – Dark Humor Sunflower Design Baseball Cap

Mandy-Sue

$20.15

~~$25.19~~ (20% off)

Alpine Optimism, Smile, Twirl, Doom, We are all going to die, funnyfits70, Humor, Funny, retro, vintage, funny quotes, animal humor, Baseball Cap

FunnyFits70

$20.06

~~$25.08~~ (20% off)

Alpine Optimism, Smile, Twirl, Doom, We are all going to die, funnyfits70, Humor, Funny, retro, vintage, funny quotes, animal humor, Dad Hat

FunnyFits70

$21.32

~~$25.08~~ (15% off)

Alpine Optimism, Smile, Twirl, Doom, We are all going to die, funnyfits70, Humor, Funny, retro, vintage, funny quotes, animal humor, Dad Hat

FunnyFits70

$21.32

~~$25.08~~ (15% off)

Item preview, "Don't Worry, We're All Gonna Die" – Dark Humor Cat Design designed and sold by A-T-H.

"Don't Worry, We're All Gonna Die" – Dark Humor Cat Design Dad Hat

A-T-H

$21.41

~~$25.19~~ (15% off)

Accident – Maryland – USA Baseball Cap

buglevel

$20.15

~~$25.19~~ (20% off)

Trying.. Baseball Cap

RipeHumor

$20.15

~~$25.19~~ (20% off)

Atomic Science 1950s Ironic Airport Funny Comic Art Dad Hat

Maljonic

$23.19

~~$27.29~~ (15% off)

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Ironic Optimism Caps

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Secure Payments

Free Return

Local Support

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