Jailbird Philosopher T-Shirts

Express your philosophical side with t-shirts that mix clever humor and deep thoughts. Ideal for jailbird philosophers who wear their ideas proudly and love making a statement.

All Products Prints T-Shirts Mugs Pillows

'Thinking outside the box eventually lead me to thinking outside the legal system.'

'Thinking outside the box eventually lead me to thinking outside the legal system.' mockup

'Thinking outside the box eventually lead me to thinking outside the legal system.'

from $19.00

"White Collar Prison"

from $19.00

Shakespeare in the clink

from $19.00

"Regards from the kids, grandma, mom and pop, uncle Fred , Aunt Theresa and cousins Harvey, Flo and Niki. They all want to know where you hid the loot."

"Regards from the kids, grandma, mom and pop, uncle Fred , Aunt Theresa and cousins Harvey, Flo and Niki. They all want to know where you hid the loot." mockup

"Regards from the kids, grandma, mom and pop, uncle Fred , Aunt Theresa and cousins Harvey, Flo and Niki. They all want to know where you hid the loot."

from $19.00

Exhibition for Prisoners

from $19.00

'My biggest mistake was to make a 'death-bed confession'... then I made a full recovery!'

'My biggest mistake was to make a 'death-bed confession'... then I made a full recovery!' mockup

'My biggest mistake was to make a 'death-bed confession'... then I made a full recovery!'

from $19.00

'Smooth move -- Now we're in REAL trouble!'

'Smooth move -- Now we're in REAL trouble!' mockup

'Smooth move -- Now we're in REAL trouble!'

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"I'm the first one in my family to do time."

"I'm the first one in my family to do time." mockup

"I'm the first one in my family to do time."

from $19.00

'Sure I do bad things, but I do them in moderation.'

'Sure I do bad things, but I do them in moderation.' mockup

'Sure I do bad things, but I do them in moderation.'

from $19.00

''Where do you see yourself in five years'? That's a stupid question! You know darn well I'll be finishing 5-years of a 25-year sentence!'

''Where do you see yourself in five years'? That's a stupid question! You know darn well I'll be finishing 5-years of a 25-year sentence!' mockup

''Where do you see yourself in five years'? That's a stupid question! You know darn well I'll be finishing 5-years of a 25-year sentence!'

from $19.00

'You're not really into this, are you Mahoney?'

'You're not really into this, are you Mahoney?' mockup

'You're not really into this, are you Mahoney?'

from $19.00

'Sweetheart, your calls are slowing my early release.'

'Sweetheart, your calls are slowing my early release.' mockup

'Sweetheart, your calls are slowing my early release.'

from $19.00

"The reason I never get any visitors is because all my family and friends are in here!"

"The reason I never get any visitors is because all my family and friends are in here!" mockup

"The reason I never get any visitors is because all my family and friends are in here!"

from $19.00

"Miss Robins, get me a ladder and a hacksaw, if you will, please."

"Miss Robins, get me a ladder and a hacksaw, if you will, please." mockup

"Miss Robins, get me a ladder and a hacksaw, if you will, please."

from $19.00

'Hey kid, what are you in for?'

from $19.00

'I made good money - until they added colour to the twenty dollar bills.'

'I made good money - until they added colour to the twenty dollar bills.' mockup

'I made good money - until they added colour to the twenty dollar bills.'

from $19.00

'MY doctor says I don't get out enough!'

'MY doctor says I don't get out enough!' mockup

'MY doctor says I don't get out enough!'

from $19.00

'Something is bothering you Roger. A wife can tell.'

'Something is bothering you Roger. A wife can tell.' mockup

'Something is bothering you Roger. A wife can tell.'

from $19.00

'It was sort of like a penalty for early withdrawal. The bank hadn't opened yet.'

'It was sort of like a penalty for early withdrawal. The bank hadn't opened yet.' mockup

'It was sort of like a penalty for early withdrawal. The bank hadn't opened yet.'

from $19.00

"The bad news is Lady Sybil has died in childbirth. On the other hand, Bates is back home and Tom's sticking around to help run the estate."

"The bad news is Lady Sybil has died in childbirth. On the other hand, Bates is back home and Tom's sticking around to help run the estate." mockup

"The bad news is Lady Sybil has died in childbirth. On the other hand, Bates is back home and Tom's sticking around to help run the estate."

from $19.00

'It's best if you take it one day at a time.'

'It's best if you take it one day at a time.' mockup

'It's best if you take it one day at a time.'

from $19.00

Love in prison.

from $19.00

'Forty-eight felony counts have taught me not to try to do everything myself.'

'Forty-eight felony counts have taught me not to try to do everything myself.' mockup

'Forty-eight felony counts have taught me not to try to do everything myself.'

from $19.00

'Look on the bright side -- we could still be in the MARKET.'

'Look on the bright side -- we could still be in the MARKET.' mockup

'Look on the bright side -- we could still be in the MARKET.'

from $19.00

'Your mother reckons you look like your baby photos now without your dandruff, dear.'

'Your mother reckons you look like your baby photos now without your dandruff, dear.' mockup

'Your mother reckons you look like your baby photos now without your dandruff, dear.'

from $19.00

'Forget about it, we all try it when we arrive here, but it's a concrete floor...'

'Forget about it, we all try it when we arrive here, but it's a concrete floor...' mockup

'Forget about it, we all try it when we arrive here, but it's a concrete floor...'

from $19.00

"It's no good you hiding, Whacker. Your release date's today and that's final!"

"It's no good you hiding, Whacker. Your release date's today and that's final!" mockup

"It's no good you hiding, Whacker. Your release date's today and that's final!"

from $19.00

'So what's your recommendation? I suggest a tunnel.'

'So what's your recommendation? I suggest a tunnel.' mockup

'So what's your recommendation? I suggest a tunnel.'

from $19.00

"I believe thr guv'nor used to own a boarding house in Blackpool."

"I believe thr guv'nor used to own a boarding house in Blackpool." mockup

"I believe thr guv'nor used to own a boarding house in Blackpool."

from $19.00

'There. Now you have the job security you've always wanted.'

'There. Now you have the job security you've always wanted.' mockup

'There. Now you have the job security you've always wanted.'

from $19.00

'For once in my life I told the truth. For this they gave me twenty years.'

'For once in my life I told the truth. For this they gave me twenty years.' mockup

'For once in my life I told the truth. For this they gave me twenty years.'

from $19.00

Con Artist.

from $19.00

Probation Officer

from $19.00

Jailbird Philosopher T-Shirts Collection

Jailbird Philosopher Mugs

Explore our collection of mugs that celebrate jailbird philosophers—witty, rebellious, and thought-provoking designs perfect for every coffee lover.

Jailbird Philosopher Pillows

Check out our pillows featuring witty and philosophical designs—great for adding a playful touch to any cozy space.

Jailbird Philosopher Prints

Browse our prints that showcase the quirky, thoughtful side of jailbird philosophers—ideal for inspiring conversations and decorating with personality.