Pessimist Caps

712 items

I already fucked up. 2025 will be my year. Baseball Cap

UnCoverDesign

$21.83

~~$27.29~~ (20% off)

Pessimist definition Baseball Cap

Amine-Creation

$19.14

~~$23.93~~ (20% off)

Pessimist Band Merch Dad Hat

xDumpTruckx

$21.41

~~$25.19~~ (15% off)

George Orwell - I told you so Baseball Cap

ValentinaHramov

$22.67

~~$28.34~~ (20% off)

Pessimist Baseball Cap

YasminSanderson

$20.15

~~$25.19~~ (20% off)

DON'T PESSIMIST BE FEMINIST Baseball Cap

PGAart

$19.31

~~$24.14~~ (20% off)

pessimist or optimist realist Dad Hat

Periush

$19.62

~~$23.09~~ (15% off)

Optimist... pessimist... SCIENTIST! Baseball Cap

Kellieenny

$20.15

~~$25.19~~ (20% off)

Optimist... Pessimist... Scientist Dad Hat

lauvjdxks

$21.41

~~$25.19~~ (15% off)

Pessimist Baseball Cap

twHistory

$20.15

~~$25.19~~ (20% off)

Pessimist Baseball Cap

twofruits2

$20.15

~~$25.19~~ (20% off)

Hang In There It Gets Worse Sarcastic Humor Cynical Pessimist Quote Dad Hat

Pessimist Baseball Cap

VOKED

$18.97

~~$23.72~~ (20% off)

Ok. Not Good. Probably Bad. Sarcastic Humor Pessimist Mood Baseball Cap

RetroMini2026

$25.19

~~$31.49~~ (20% off)

Pessimist Baseball Cap

AUTOPSY666

$20.15

~~$25.19~~ (20% off)

Pessimist Baseball Cap

Dj Gavric998

$20.15

~~$25.19~~ (20% off)

Swing both ways joke Baseball Cap

T&C Finesse

$20.15

~~$25.19~~ (20% off)

A "Realist" is just a Pessimist in Denial - Cheerful 70's Version Dad Hat

PHNDZMND

$21.41

~~$25.19~~ (15% off)

A "Realist" is just a Pessimist in Denial Dad Hat

PHNDZMND

$21.41

~~$25.19~~ (15% off)

Pessimist Baseball Cap

Optimist... Pessimist... Scientist (1) Dad Hat

lauvjdxks

$21.41

~~$25.19~~ (15% off)

Pessimist Baseball Cap

foreverfictionl

$20.15

~~$25.19~~ (20% off)

Pessimist Baseball Cap

A "Realist" is just a Pessimist in Denial - Fancy Version Dad Hat

PHNDZMND

$21.41

~~$25.19~~ (15% off)

Aquarium Optimist Pessimist Aquarist Fish Dad Hat

CruzJane

$21.41

~~$25.19~~ (15% off)

George Orwell - I told you so Baseball Cap

ValentinaHramov

$22.67

~~$28.34~~ (20% off)

Borrow Money From Pessimist Baseball Cap

LoboTomica

$20.15

~~$25.19~~ (20% off)

Doughnut Philosophy Funny Quote Dad Hat

Horningamere

$19.62

~~$23.09~~ (15% off)

The Pessimist’s cookbook Dad Hat

BertHall

$21.41

~~$25.19~~ (15% off)

The Poet of Pessimism Baseball Cap

Art School Dropout

$18.47

~~$23.09~~ (20% off)

chronic pessimist Baseball Cap

JustAnotherBee

$20.15

~~$25.19~~ (20% off)

Optimist Pessimist Engineer Funny Tee Dad Hat

MilasKloser

$23.19

~~$27.29~~ (15% off)

Bald Head Island NC Vintage 70s Retro Throwback Design T-Shirt Baseball Cap

CruzJane

$20.15

~~$25.19~~ (20% off)

Why does there have to be a day every day? Can't we get one day off? Baseball Cap

ThatIsSomething

$20.15

~~$25.19~~ (20% off)

George Bernard Shaw Quote Baseball Cap

PatSeg Photos

$20.15

~~$25.19~~ (20% off)

Ok. Not Good. Probably Bad. Funny Sarcastic Relatable Mood Quote Baseball Cap

HumansStuck12

$25.19

~~$31.49~~ (20% off)

Misanthropic Humanist - Sticker Dad Hat

GnomeEnthusiast

$19.62

~~$23.09~~ (15% off)

optimist pessimist realist - fagottist Baseball Cap

kobyakov

$20.15

~~$25.19~~ (20% off)

Freaking Optimist | Funny Optimism | Ironic Pessimist Baseball Cap

MadamBullmoose

$20.15

~~$25.19~~ (20% off)

i'm done t shirt Dad Hat

I had my patience tested, I'm negative Baseball Cap

Compusmurf Design

$20.15

~~$25.19~~ (20% off)

Professional Pessimist. Dad Hat

Witch Queen Clothing

$21.41

~~$25.19~~ (15% off)

Sunny Pessimist Dad Hat

foreverfictionl

$21.41

~~$25.19~~ (15% off)

Eternal Pessimist Dad Hat

livelaughhell

$21.41

~~$25.19~~ (15% off)

optimist pessimist realist - bassoonist Dad Hat

kobyakov

$21.41

~~$25.19~~ (15% off)

Funny Pessimist Dad Hat

HappyHavenStu

$21.41

~~$25.19~~ (15% off)

the pessimist Baseball Cap

TOOTIFROOTI merch

$20.15

~~$25.19~~ (20% off)

Optimist, Pessimist & Realist Dad Hat

UrTshirt

$19.62

~~$23.09~~ (15% off)

If There Was An Award For Pessimism, I Probably Wouldn't Even Be Nominated Baseball Cap

Good-Looking Corpse

$21.83

~~$27.29~~ (20% off)

Sunny Pessimist Baseball Cap

foreverfictionl

$20.15

~~$25.19~~ (20% off)

Have you heard the bad news? Baseball Cap

Domain of the Public

$20.15

~~$25.19~~ (20% off)

Pessimist. | A design that says Pessimist. Dad Hat

chestify

$23.19

~~$27.29~~ (15% off)

Emotional prostate exam Dad Hat

PinkDuckTees

$21.41

~~$25.19~~ (15% off)

My rose-colored glasses have thorns Baseball Cap

RickPostCo

$20.15

~~$25.19~~ (20% off)

Noah Fence - Everything Sucks! Dad Hat

chicksdoings

$21.41

~~$25.19~~ (15% off)

Everything Sucks Baseball Cap

AMangoTees

$20.15

~~$25.19~~ (20% off)

Everything Sucks Baseball Cap

AMangoTees

$20.15

~~$25.19~~ (20% off)

Oblivion Baseball Cap

Life sucks and then you die Baseball Cap

MrDaddyTs

$18.47

~~$23.09~~ (20% off)

Clearly overthinking is not a problem for you Dad Hat

EdifiedExpressions

$19.62

~~$23.09~~ (15% off)

People Suck Baseball Cap

RMH23

$18.47

~~$23.09~~ (20% off)

No Karen Baseball Cap

Peter Stawicki

$18.47

~~$23.09~~ (20% off)

Programmer Logic Baseball Cap

Regin Productions

$20.15

~~$25.19~~ (20% off)

work really hard and this could be you Dad Hat

caddystar

$21.41

~~$25.19~~ (15% off)

Whatever Fuck It Dad Hat

HiddenStar02

$21.41

~~$25.19~~ (15% off)

What's The Point? Baseball Cap

artpirate

$20.15

~~$25.19~~ (20% off)

There's Always Something And It Never Ends Dad Hat

Good-Looking Corpse

$23.19

~~$27.29~~ (15% off)

Team Introvert Dad Hat

NO FUTURE Baseball Cap

FREE T-Shirts

$20.15

~~$25.19~~ (20% off)

Illustration of Arthur Schopenhauer - a German philosopher, representative of pessimism Dad Hat

billky

$21.41

~~$25.19~~ (15% off)

Warning: Pessimist Ahead! Dad Hat

VaniTee Fair

$19.62

~~$23.09~~ (15% off)

Polite Pessimist Collection Dad Hat

Schrodinger's Clothing

$19.62

~~$23.09~~ (15% off)

Rimworld Pessimist Trait Dad Hat

gilbertgraham

$23.19

~~$27.29~~ (15% off)

Optimist Pessimist Engineer Dad Hat

TeesYouWant

$35.68

~~$41.98~~ (15% off)

pessimist in black Dad Hat

sofilustra

$23.19

~~$27.29~~ (15% off)

Professional Pessimist Collection Baseball Cap

Schrodinger's Clothing

$18.47

~~$23.09~~ (20% off)

Vintage Political Insult for Media and Pessimists Baseball Cap

MadamBullmoose

$20.15

~~$25.19~~ (20% off)

If You Just Give Me A Minute I Think I Can Make It Worse Sarcasm Humor Quote Pessimist Baseball Cap

SofenArt

$20.15

~~$25.19~~ (20% off)

Murphy More Insightful Than Credited Funny Design Baseball Cap

FuddalanDesigns

$23.51

~~$29.39~~ (20% off)

your local pessimist Dad Hat

ksdc90

$23.19

~~$27.29~~ (15% off)

The classic Grump/Sunshine combo Dad Hat

marginaliapod

$23.19

~~$27.29~~ (15% off)

George Orwell - I told you so Dad Hat

ValentinaHramov

$24.08

~~$28.34~~ (15% off)

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Pessimist Caps

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