31 Funny Vintage Christmas Family Pics, Ads & Pinups

Awkward Vintage Christmas Family Photos, Vintage Christmas Ads, Pinup Girl Posters, Christmas Cards

Flashback to a Funny Vintage Christmas & New Year’s

Have you been a good boy or girl this year? Well, Santa will be the judge of that. Doesn’t matter. You can enjoy this hilarious dump of vintage Christmas photos and classic vintage ads. There are also a vast, funny array of awkward family photos and some creepy Santas, and rare vintage pinup girl posters. As strange as the Christmas pinup girl photos may seem now, I’m sure they went a long way to lift the holiday spirits of our WWII troops. And heck, they might inspire you to create your own sexy Christmas cards this year. So step back into the mid-century and enjoy this fun and awkward batch of Christmas madness.

 

Vintage Christmas ad, Santa drinking, it's the most wonderful time for a beer.

 

While you have to admire this girl’s new mod 1960s outfit, we just want to know how happy mom was with her handy present under three…  Look closely… it’s a Dustbuster!

Vintage awkward Christmas family phots, 1960s pre-teen in mod outfit next to tree. dustbuster present

 

Vintage Christmas, 1960s, The Beach Boys decorating tree

 

This girl sitting on creepy Santa’s lap may not be totally freaked-out by Santa’s man boob beard, but I’ll never sleep soundly ever again!

Awkward family Christmas, giirl sitting on creepy Santa's lp. Santa has man boobs on beard.

 

Ya think the free parking for Santa is inside her warm garage?

Vintage 1940s Christmas pin-up. Free parking for Santa.

 

WHen they were young, Bill Murray posing in Christmas wreath.

 

Vintage Christmas ads, fake spray-on Christmas tree snow

 

Funny gif from Charlie Brown Christmas special, characters dancing

 

Good ol’ Anna Nicole Smith with her sugar daddy husband, just not sure if it was before or after his death.

Creepy awkward Christmas photo. Ana Nicole Smith posing with old husband in fron of tree.

 

Does Santa make you horny, baby?

Vintage Christmas illustration sexy Santa

 

Awkward family Christmas photos, family Christmas cards, Goth daughter

 

Someone hide the carving knife from O.J.

Vintage Christmas ad with O.J. Simpson Christmas Card, Happy Holidays

 

Vintage illustration Harley Toy Ru, Santa biker

 

Never quite understood why Tom & Jerry appeared on so many pinup posters.

Vintage Christmas pin-up. with Tom & Jerry 1940s

 

Vintage cards, awkward family photos, soldier, air force taking pics

 

Vintage Christmas adult comics, pin-up

 

Expmais where the Yule log came from.

Funny Christmas pics, Santa pooping down chimney

 

The damaging effects that exposure to too much Mariah Carey and George Michaels has on the brain.

funny Christmas pics violent hallucinations caused by Christmas music.

 

Vintage christmas gif, vintage TV commercial Santa Camel cigarettes

 

Vintage christmas ads, Santa smoking cigarette

 

“Oh, look. There’s a bulb that’s burned out. Don’t get up. I’ll get it.”

Vintage awkward family Christmas photos, glamorous mom posing in front of tree.

 

Just way too much going on here to unpack.

Vintage Family Christmas photos, ads, 1944

 

Christmas Christmas ad. Mick Jagger Santa.

 

Vintage Christmas movie poster. Santa Claus Conquers the Martians.

 

What’s up with Santa’s severed head on her lap?

Vintage Christmas pin-up, sexists ads, adult comics

 

Funny gif of abominable snowman from classic Rudolph the red nosed reigndeer TV special

 

Grandpa finally got the little son that mother could never give him.

Christmas awkward family photos, Vintage grandpa and grandma posing with blow-up Santa doll.

 

vintage Christmas pin-up ad 1940s. Woman in Santa hat sitting on ice pblick feeding dog ice cream.

 

vintage awkward family Christmas photo. 1970s fashions mon posing in front of tree.

 

Vintage 1970s Christmas catalogue ad. Family sitting beneath tree with dad getting tools as gifts.

 

Happy New Year’s everyone!

vintage Christmas and new year's pin-up from 1953. Woman sitting on a star

Visited 9181 times, 1 visit(s) today

Show Comments

No Responses Yet

What'cha got to say for yourself?

This site uses Akismet to reduce spam. Learn how your comment data is processed.