Jail Caps

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1000+ items

Chibi Girl Trapped Baseball Cap

BambinoBunnyyy

$23.09

Chibi Girl Trapped Dad Hat

BambinoBunnyyy

$23.09

Eastern State Penitentiary Starry Night Historical Landscape Dad Hat

Bad-Decisions-Designs

$23.09

Got Too Silly_ Caged Pigeon Doodle Baseball Cap

pmjv-csv

$28.34

Con Air Classic Movie 1 Baseball Cap

Briancreek-A

$30.44

Shawshank Penitentiary Starry Night Landscape Baseball Cap

Bad-Decisions-Designs

$23.09

Item preview, Funny Trump Behind Bars - Satirical Political Caricature Make America Great Again Parody designed and sold by Christopher McGuire.

Funny Trump Behind Bars - Satirical Political Caricature Make America Great Again Parody Baseball Cap

Christopher McGuire

$25.19

Correctional Nurse American Flag Dad Hat

anapldv

$23.09

Dark Comic Book Skeleton Jail Guitar Staying Home Slogan Baseball Cap

StephanieKluge

$25.19

Madness Jail Cell Skeleton Hands Dad Hat

BodybagCrypt

$23.09

a goose behind "GOT TOO SILLY". Dad Hat

Designart68

$24.77

Got Too Silly Funny Goose Jail Meme Dad Hat

will freed18

$24.14

Got Too Silly Duck in Jail Funny Meme Baseball Cap

will freed18

$24.14

Repeat Offender Dad Hat

MohammedBoueyK

$25.19

Rikers Island Baseball Cap

UNK-Fatigues

$27.29

Old Castlemaine Gaol Baseball Cap

D-GaP

$25.19

Talloween: Why We Can’t Have Nice Things Dad Hat

Karate Octopus

$23.09

Talloween: For Those Banned from Mardi Gras for Bad Behavior Dad Hat

Karate Octopus

$23.09

Thou Shall Not Go To Jail For Tacos Dad Hat

We All Shine Ynw Melly Free Jail Mugshot Amelie Lens Dad Hat

ThatByMattz

$25.19

Be Nice To Your Dice They're Trying Their Best Baseball Cap

KristiTaylorArt

$25.19

Talloween Baseball Cap

Karate Octopus

$23.09

Talloween: Don’t Eat the Blue Candy Corn Baseball Cap

Karate Octopus

$23.09

I Wonder How Much Jail Time I'd Get If I Really Did Unto Others As They've Done Unto Me Baseball Cap

ismaelgeme

$25.19

Prison Cell Illustration with Bars and Locked Door Design Dad Hat

coldhorizon

$32.74

Rikers Island Dad Hat

UNK-Fatigues

$27.29

Corrections Officer – Thin Silver Line Correctional Officer Pride Dad Hat

artistwill

$25.19

I CAN FIX STUPID BUT I MAY GO TO JAIL AND FOR SURE WILL GET FIRED Baseball Cap

CRINGEWORTHY TEES

$24.73

Talloween Arrestometer Baseball Cap

Karate Octopus

$23.09

Funny Cartoon Characters in a Jail Scene Baseball Cap

elijbclaude

$23.09

Just Did My Own Taxes...... Dad Hat

Batzdavie

$23.09

Just Did My Own Taxes...... Dad Hat

FrogPaintLab

$23.09

Rikers Island Dad Hat

UNK-Fatigues

$27.29

Mitch totally not a corpse puppet Baseball Cap

reallypathetic

$25.19

Talloween 2026: Free Police Car Rides Baseball Cap

Karate Octopus

$23.09

Pledgeescobar Penn State White Out Dad Hat

DestiniHill

$25.19

Pablo Pledgeescobar Graphic Baseball Cap

DestiniHill

$25.19

Talloween 2026: Dad, I Need Bail Money Dad Hat

Karate Octopus

$23.09

Isnt It Past Your Jail Time Baseball Cap

Talloween Mug Shot Dad Hat

Karate Octopus

$23.09

The Judge Ruled I Was at Talloween 2026 Dad Hat

Karate Octopus

$23.09

Talloween 2026: Paroled Dad Hat

Karate Octopus

$23.09

Talloween 2026: Come for the Party, Stay for the Sentencing Baseball Cap

Karate Octopus

$23.09

Got Too Silly Prison Goose Dad Hat

ClarissaDoodles

$23.09

Talloween 2026: Spend the Night in the Leon County Jail Dressed As a Sexy Cat Dad Hat

Karate Octopus

$23.09

Talloween Taxi Co. Baseball Cap

Karate Octopus

$23.09

Got Too Silly - Silly Goose Meme Baseball Cap

Ibrahimott

$25.19

VOTE - Because He Won't Impeach Himself Baseball Cap

HumanKindMedia

$23.09

VOTE - Democracy Won't Defend Itself. Baseball Cap

HumanKindMedia

$23.09

VOTE - Because Trump won't prosecute himself Dad Hat

HumanKindMedia

$23.09

VOTE - Because Trump won't prosecute himself Dad Hat

HumanKindMedia

$23.09

Dozy Don can't talk without passing out Dad Hat

reallypathetic

$25.19

Lock Him Up Chance Card Go To Jail Dad Hat

ZahiraFi-reston

$25.19

Trump In Jail 2024 (Trump The Criminal) Dad Hat

Bayle-ighHu

$25.19

Suburban Prisoners History Thriller Cinema Movie Clan Baseball Cap

Cine8

$23.09

wolf special black and white Baseball Cap

CosmicHollow

$25.40

Sadist - Something to Pierce album 2025 Baseball Cap

CosmicHollow

$25.40

Lock Him Up - Jail Trump Dad Hat

Anja Gillette

$25.19

Jail To The Thief Send Trump To Jail Lock Him Up Dad Hat

Anja Gillette

$25.19

Rikers Island Baseball Cap

UNK-Fatigues

$27.29

Black Raven Bird Prison Thriller Cinema Movie Poster Dad Hat

Cine8

$23.09

Funny Prisgeon Prisoner Pigeon Pun Bird Joke Baseball Cap

Hilal-Studio

$23.09

Talk Your Way Into Jail Baseball Cap

Atlantapig

$25.19

Grumpy Got Too Silly Raccoon Behind Bars Dad Hat

Lozarux

$26.24

The Shawshank Redemption (Comic book version) Dad Hat

tigrootiger

$25.19

On Day Release Dad Hat

CSupernova

$23.51

Play the guitar, play it again, my Johnny (B Edition) Dad Hat

PrivateVices

$25.19

Vienna vs. Emma Small Dad Hat

PrivateVices

$25.19

Play the guitar, play it again, my Johnny (Version 2026) Dad Hat

PrivateVices

$25.19

Rikers Island Dad Hat

UNK-Fatigues

$27.29

Kurapika Hunter x Hunter Scarlet Eyes Baseball Cap

SirLivy

$25.19

Skeleton Jail Cage Dad Hat

Blems

$25.19

Got Too Silly Goose Going To Jail Meme Baseball Cap

Sartoris Art

$25.19

Poster Freedom - The Shawshank Redemption Andy Dufresne Painting Dad Hat

Nicole-gibson

$30.65

Straight Out Of Prison, Funny Inamte, Out Of Jail Quotes Dad Hat

Colorfulman

$26.24

Man In Sunglasses Smoking Behind Bars Dad Hat

West Barn ⭐⭐⭐⭐⭐

$23.09

My Bag of Holding Is a Crime Scene — TTRPG Humor Design Dad Hat

Wanderquill Studio

$24.14

Too Many Kerfuffles Frog in Jail Baseball Cap

Szpaku desart

$25.19

Juice Aint Free Baseball Cap

Daviscoatings

$25.19

Juice Aint Free Dad Hat

Daviscoatings

$25.19

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Jail Caps

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