Pessimistic Caps

984 items

Sad Eeyore Quote Baseball Cap

Unhinged Heather

$20.99

~~$26.24~~ (20% off)

Black Is My Favorite Color Dad Hat

kjanedesigns

$21.41

~~$25.19~~ (15% off)

It's going to get worse Dad Hat

Rosefurn

$24.09

~~$28.34~~ (15% off)

Burn It Down, Flowers Don't Care Dad Hat

ShadowCatArtCo

$23.19

~~$27.29~~ (15% off)

hang in there, worse, office humor, attitude, funnyfits70, Humor, Funny, retro, vintages, funny quotes, animal humor, Dad Hat

FunnyFits70

$21.32

~~$25.08~~ (15% off)

Eeyore Quote About Kindness Baseball Cap

Unhinged Heather

$20.99

~~$26.24~~ (20% off)

Sad Eeyore Quote Dad Hat

Unhinged Heather

$22.30

~~$26.24~~ (15% off)

Item preview, funny influence sarcastic offended saying bad but damn fun gift Birthday Meme Girlfriend boyfriend designed and sold by joygift369.

funny influence sarcastic offended saying bad but damn fun gift Birthday Meme Girlfriend boyfriend Dad Hat

joygift369

$21.94

~~$25.82~~ (15% off)

Pessimist definition Baseball Cap

Amine-Creation

$19.14

~~$23.93~~ (20% off)

HAPPY RAY OF FUCKING SUNSHINE Dad Hat

artbySC

$21.94

~~$25.82~~ (15% off)

Bad vibes only Baseball Cap

NemiMakeit

$20.15

~~$25.19~~ (20% off)

optimist pessimist empathy Dad Hat

Pessimistic Baseball Cap

Dj Gavric998

$20.15

~~$25.19~~ (20% off)

Life is pointless Dad Hat

ReAnnaMation

$21.41

~~$25.19~~ (15% off)

Pessimistic people tshirt Dad Hat

Things are bad - plastic bag design Dad Hat

Lauren Cuppy

$26.76

~~$31.49~~ (15% off)

Just no. Baseball Cap

StickyGoddess

$20.15

~~$25.19~~ (20% off)

You’re Doing Amazing Printable Quote – Funny Mental Health | Sarcastic Encouragement Gift Baseball Cap

Squish The Bug

$19.31

~~$24.14~~ (20% off)

Pessimistic Classic Baseball Cap

Anavzla

$23.17

~~$28.97~~ (20% off)

Pessimistic Meowmy Baseball Cap

BeeHappyShop

$21.66

~~$27.08~~ (20% off)

Pessimistic pacifist Dad Hat

bonkn beeps

$23.19

~~$27.29~~ (15% off)

Pessimistic Optimism Quote Baseball Cap

AuraDesignz

$22.67

~~$28.34~~ (20% off)

Pessimistic Calli Dad Hat

Everything Sucks Dad Hat

AMangoTees

$21.41

~~$25.19~~ (15% off)

Bojack Horseman's Mother | Beatrice Horseman | Dirt for Inside (Variant) Dad Hat

DemonicSalt

$21.41

~~$25.19~~ (15% off)

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

Good-Looking Corpse

$23.19

~~$27.29~~ (15% off)

Dark thoughts Dad Hat

eri-morie

$23.37

~~$27.50~~ (15% off)

Could be worse. I could be stupid. Baseball Cap

Double-Dome

$20.15

~~$25.19~~ (20% off)

Everything Sucks Baseball Cap

Life is Hard Quote Dad Hat

RowiKiwi

$21.41

~~$25.19~~ (15% off)

It’ll get worse Dad Hat

comrademittens

$21.41

~~$25.19~~ (15% off)

Science is Optimistic Dad Hat

nextneveldesign

$25.87

~~$30.44~~ (15% off)

Science is Optimistic Baseball Cap

nextneveldesign

$24.35

~~$30.44~~ (20% off)

Life Is Soup and I Am a Fork Baseball Cap

Trexyca Artworks Store

$20.15

~~$25.19~~ (20% off)

YES I CAN('T) Dad Hat

NadyaCC

$20.20

~~$23.77~~ (15% off)

Thinking Positive Dad Hat

Trendi-Design

$23.19

~~$27.29~~ (15% off)

trying my best Dad Hat

Science is Optimistic Baseball Cap

nextneveldesign

$24.35

~~$30.44~~ (20% off)

I'm not pessimistic, I'm just well informed. Saying in German - funny Dad Hat

Pflugart

$19.27

~~$22.67~~ (15% off)

Science is Optimistic Dad Hat

nextneveldesign

$25.87

~~$30.44~~ (15% off)

Science is Optimistic Baseball Cap

nextneveldesign

$24.35

~~$30.44~~ (20% off)

Science is Optimistic Dad Hat

nextneveldesign

$25.87

~~$30.44~~ (15% off)

OK. Not Good. Probably Bad. Sarcastic Humor Relatable Mood Quote Dad Hat

HumansStuck12

$26.76

~~$31.49~~ (15% off)

Science is Optimistic Dad Hat

nextneveldesign

$25.87

~~$30.44~~ (15% off)

Science is Optimistic Baseball Cap

nextneveldesign

$24.35

~~$30.44~~ (20% off)

Capricorn Baseball Cap

OpusDay

$18.47

~~$23.09~~ (20% off)

Funny 8bit Pixel Text Quote Baseball Cap

BoggsNicolasArt

$20.15

~~$25.19~~ (20% off)

Science is Optimistic Dad Hat

nextneveldesign

$25.87

~~$30.44~~ (15% off)

. Wim Avril stoss. Darkness and Hope. (The Edited) Baseball Cap

Wim Avril Stoss

$20.15

~~$25.19~~ (20% off)

Depressed Santa Claus Dad Hat

masterchef-fr

$19.62

~~$23.09~~ (15% off)

Hang In There It Gets Worse Funny Relatable Sarcastic Quote Dad Hat

RetroMini2026

$26.76

~~$31.49~~ (15% off)

Science is Optimistic Baseball Cap

nextneveldesign

$24.35

~~$30.44~~ (20% off)

Wittgenstein Rabbit Duck Illusion Baseball Cap

PAULABIG

$20.15

~~$25.19~~ (20% off)

I am pessimistic emotion and mood Baseball Cap

Therapy by Sen

$25.19

~~$31.49~~ (20% off)

Unredeemable Monster Dad Hat

Steve Yao

$21.41

~~$25.19~~ (15% off)

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

JonesFlora2025

$25.19

~~$31.49~~ (20% off)

There's Always Something And It Never Ends Dad Hat

Good-Looking Corpse

$23.19

~~$27.29~~ (15% off)

I am not pessimistic. I am just well informed. Baseball Cap

Pflugart

$18.13

~~$22.67~~ (20% off)

Emotional pack Baseball Cap

chuckletuckle

$19.98

~~$24.98~~ (20% off)

Height Classic Baseball Cap

Gloriacleopat

$20.15

~~$25.19~~ (20% off)

I am pessimistic emotion and mood Dad Hat

Therapy by Sen

$26.76

~~$31.49~~ (15% off)

How Much Worse Dad Hat

HandsOffMyDinosaur

$21.41

~~$25.19~~ (15% off)

Those who doubt my ability. Baseball Cap

unspired

$20.15

~~$25.19~~ (20% off)

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

RetroMini2026

$25.19

~~$31.49~~ (20% off)

I Want To Go Home. I Hate Camping Dad Hat

Shauntoleary

$25.33

~~$29.81~~ (15% off)

Anyone notice anything strange about the weather reports from hell Baseball Cap

mntimg

$20.15

~~$25.19~~ (20% off)

Eat healthy, stay fit, die anyway. Dad Hat

It will probably get worse. Dad Hat

I'm not pessimistic, I'm just well informed. Saying in German - funny Dad Hat

Pflugart

$19.27

~~$22.67~~ (15% off)

You can always be replaced. Baseball Cap

unspired

$20.15

~~$25.19~~ (20% off)

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

HumansStuck12

$25.19

~~$31.49~~ (20% off)

Feeling Bearish Dad Hat

sheprint

$21.41

~~$25.19~~ (15% off)

Crystal Ball Fortune: It Gets Worse Dad Hat

RowiKiwi

$21.41

~~$25.19~~ (15% off)

Reach for the stars, follow your dreams Baseball Cap

When in doubt, chicken out. Baseball Cap

unspired

$20.15

~~$25.19~~ (20% off)

Not in the Mood Grumpy Face Emoji Illustration Dad Hat

jingenuity

$20.52

~~$24.14~~ (15% off)

It's all downhill from here. Baseball Cap

unspired

$20.15

~~$25.19~~ (20% off)

If you never believe in yourself, you'll never let yourself down. Dad Hat

unspired

$21.41

~~$25.19~~ (15% off)

Others can't use you if you're useless. Baseball Cap

unspired

$20.15

~~$25.19~~ (20% off)

Pessimism Killer Baseball Cap

Bloom and Doom Baseball Cap

LatonaGoods

$20.15

~~$25.19~~ (20% off)

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Pessimistic Caps

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