Mid-life Milestone Pillows

Our pillows bring comfort and humor to mid-life milestones, offering cozy reminders of this unforgettable time and making everyday moments special.

All Products Prints T-Shirts Mugs Pillows

Getting old...

from $19.00

'I refuse to relinquish the title, 'Top Young Exec'.'

'I refuse to relinquish the title, 'Top Young Exec'.' mockup

'I refuse to relinquish the title, 'Top Young Exec'.'

from $19.00

'An old-looking guy held the door for me today, and called me 'sir'.'

'An old-looking guy held the door for me today, and called me 'sir'.' mockup

'An old-looking guy held the door for me today, and called me 'sir'.'

from $19.00

"Hot flashes?"

from $19.00

'He's been like this ever since he had his laser eye treatment.'

'He's been like this ever since he had his laser eye treatment.' mockup

'He's been like this ever since he had his laser eye treatment.'

from $19.00

Cardiac Recovery.

from $19.00

"I’ve settled comfortably into middle-age while Barry has settled comfortably into Middle Earth."

"I’ve settled comfortably into middle-age while Barry has settled comfortably into Middle Earth." mockup

"I’ve settled comfortably into middle-age while Barry has settled comfortably into Middle Earth."

from $19.00

'See? You call my look 'a midlife crisis' but for these guys it's a major TV series.'

'See? You call my look 'a midlife crisis' but for these guys it's a major TV series.' mockup

'See? You call my look 'a midlife crisis' but for these guys it's a major TV series.'

from $19.00

Church Basement Foodie

from $19.00

'I used to spring forward. Now all I can do is fall back.'

'I used to spring forward. Now all I can do is fall back.' mockup

'I used to spring forward. Now all I can do is fall back.'

from $19.00

"Faster! Middle age is gaining on you!" mockup

"Faster! Middle age is gaining on you!"

from $19.00

"The third little pig is now a menopausal porker. I hate these hairs on my chinny chin chin."

"The third little pig is now a menopausal porker. I hate these hairs on my chinny chin chin." mockup

"The third little pig is now a menopausal porker. I hate these hairs on my chinny chin chin."

from $19.00

"You're crappin' in the closet again, Claude."

"You're crappin' in the closet again, Claude." mockup

"You're crappin' in the closet again, Claude."

from $19.00

Middle Age: When you finally get your head together, and your body starts to fall apart!

Middle Age: When you finally get your head together, and your body starts to fall apart! mockup

Middle Age: When you finally get your head together, and your body starts to fall apart!

from $19.00

"Enjoy yourself while you can because before you know it, you've surpassed your 'Best Used By' date."

"Enjoy yourself while you can because before you know it, you've surpassed your 'Best Used By' date." mockup

"Enjoy yourself while you can because before you know it, you've surpassed your 'Best Used By' date."

from $19.00

Rock and Roll

from $19.00

"I'm here for the hair."

from $19.00

An old man exercising with hourglasses mockup

An old man exercising with hourglasses

from $19.00

"Good news, honey - seventy is the new fifty."

"Good news, honey - seventy is the new fifty." mockup

"Good news, honey - seventy is the new fifty."

from $19.00

"I'm 59 and they say I'm middle aged. Just how many people do you know who are 118?"

"I'm 59 and they say I'm middle aged. Just how many people do you know who are 118?" mockup

"I'm 59 and they say I'm middle aged. Just how many people do you know who are 118?"

from $19.00

The best way to prevent sagging is to keep eating until the wrinkles fall out.

The best way to prevent sagging is to keep eating until the wrinkles fall out. mockup

The best way to prevent sagging is to keep eating until the wrinkles fall out.

from $19.00

"This old bike of mine has sure lost some if its speed over the years."

"This old bike of mine has sure lost some if its speed over the years." mockup

"This old bike of mine has sure lost some if its speed over the years."

from $19.00

We micro-grafted all the hairs from the back of your head to the top and now we've completely covered your bald spot.'

We micro-grafted all the hairs from the back of your head to the top and now we've completely covered your bald spot.' mockup

We micro-grafted all the hairs from the back of your head to the top and now we've completely covered your bald spot.'

from $19.00

'Here's your chance to become a legend.'

'Here's your chance to become a legend.' mockup

'Here's your chance to become a legend.'

from $19.00

"You're right, they are statins." mockup

"You're right, they are statins."

from $19.00

"The nest may be empty, but our drinks are full."

"The nest may be empty, but our drinks are full." mockup

"The nest may be empty, but our drinks are full."

from $19.00

You know you're getting older: when your back goes out more often than you do!

You know you're getting older: when your back goes out more often than you do! mockup

You know you're getting older: when your back goes out more often than you do!

from $19.00

"Put it under your pillow, and maybe you'll get a visit from the hair fairy."

"Put it under your pillow, and maybe you'll get a visit from the hair fairy." mockup

"Put it under your pillow, and maybe you'll get a visit from the hair fairy."

from $19.00

Medication for the elderly

from $19.00

Male Pattern Baldness

from $19.00

"Day 19,918: Once again, Gary cannot believe he's still alive."

"Day 19,918: Once again, Gary cannot believe he's still alive." mockup

"Day 19,918: Once again, Gary cannot believe he's still alive."

from $19.00

"My once perky chicken breasts hang like flapjacks, I don't lay eggs anymore, I'm burning up with hot flashes, I'm...."

"My once perky chicken breasts hang like flapjacks, I don't lay eggs anymore, I'm burning up with hot flashes, I'm...." mockup

"My once perky chicken breasts hang like flapjacks, I don't lay eggs anymore, I'm burning up with hot flashes, I'm...."

from $19.00

Middle Age: When rolling out of bed is easy, but getting up off the floor isn't!

Middle Age: When rolling out of bed is easy, but getting up off the floor isn't! mockup

Middle Age: When rolling out of bed is easy, but getting up off the floor isn't!

from $19.00

"You've come to a fork in the road – age-defying or age-appropriate?"

"You've come to a fork in the road – age-defying or age-appropriate?" mockup

"You've come to a fork in the road – age-defying or age-appropriate?"

from $19.00

"From Zero To Sixty In What Seems Like Eight Seconds Flat."

"From Zero To Sixty In What Seems Like Eight Seconds Flat." mockup

"From Zero To Sixty In What Seems Like Eight Seconds Flat."

from $19.00

Mid-life Milestone Pillows Collection

Mid-life Milestone Mugs

Find the perfect mug to celebrate a mid-life milestone, combining humor and sentiment for memorable mornings.

Mid-life Milestone Prints

Decorate with prints that commemorate mid-life milestones, blending personality and style for meaningful home decor.

Mid-life Milestone T-Shirts

Browse our collection of t-shirts that mark mid-life achievements with wit and style, making great gifts for this special time.