vintage art of children nestled in their beds on Christmas eve

10 Slightly Weird Pieces of Vintage Christmas Art and Illustrations

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I do love a little weirdness in my art. From the surreal and fantastical scenes Bella Ormseth creates to Pedro Correa’s bizarro illustrations, I’m down for some oddity.

This includes vintage illustrations that look creepy by today’s standards. Not all of the following vintage Christmas art is strange – I balanced it out with some tame holiday visuals so you wouldn’t have nightmares tonight.

But starting with this first image, there is plenty here to put some extra jingle in your jangle if you enjoy a side of discomfort while looking at art. No idea what that means.

This wasted Santa does not give 2 hoots that he is scarring the sweet cherubic child next to him for life.

The kid attempts to show Santa what he wants for Xmas, and is met with the uproarious laughter of someone who is just so done for the year. Also…. does Santa have hooves?

Christmas 1896 (1896) by J. Ottman Lithographic Company. Original from Library of Congress. Digitally enhanced by rawpixel

I give you a brief respite with this lovely bird in a globe illustration. I love the idea of printing and framing this and pulling it out as a subtle Christmas decoration every year.

Winter bird illustration from The Child’s Book of Poetry. A selection of poems, ballads and hymns (1886) published by R.T.S. London. Original from the British Library. Digitally enhanced by rawpixel

Time to move onto everybody’s favorite Medieval artist, Hieronymus Bosch. Are you as confused as I am by the tiny man-Jesus?

The Nativity (ca. 1550–1600) by Jheronimus Bosch. Original from The Rijksmuseum. Digitally enhanced by rawpixel

This one is so interesting. It looks modern, but was created in 1914. The ornaments are so funny, and the tree is a super-cool minimal design. I really want to see this turned into an animated Christmas special, please.

L’Arbre Merveilleux – Costumes d’enfants pour Nöel (1914) by Charles Martin. Original from The Rijksmuseum. Digitally enhanced by rawpixel

Enjoy this holly, because the next image is full of Christmas mayhem.

Christmas dinner with holly leaves (1899) from The Buttolph collection of menus. Original From The New York Public Library. Digitally enhanced by rawpixel

My favorite human in this vintage Christmas illustration is the fella in the bottom center. His goggles and bottle of horse liniment have me utterly confused, and somehow he steals the glory from the Christmas tree.

Christmas Tree (1902) by J. Ottman Lithographic Company. Original from Library of Congress. Digitally enhanced by rawpixel

I am assuming this vintage Christmas card was supposed to be charming with its winter flora and fauna scenes, but it quickly goes dark with the rabbit contemplating the trap in the third frame.

Christmas Card Depicting Winter Landscapes with Dogs, Rabbits, and Birds (1865–1899) by L. Prang & Co. Original from The New York Public Library. Digitally enhanced by rawpixel

I’m a sucker for vintage illustrations of children nestled in their cozy beds dreaming of sweets and presents. I love how it’s easy to not notice these sweets have legs with which they are actually dancing and frolicking about.

The children were nestled all snug in their beds by Jessie Wilcox Smith (1863-1935). Original from The New York Public Library. Digitally enhanced by rawpixel

These 2 red and white floating Christmas figures were no doubt meant to look chic, but they kind of scare me. They seem so randomly placed on the patterned background, and both have spooky expressions.

Christmas Poster (1895) by Will Bradley. Original from The New York Public Library. Digitally enhanced by rawpixel

I adore this illustration of a woman holding a muff and her little dog running along beside her. The wreath is the perfect amount of Christmas, and all of the light green outlines are unexpected and lovely.

Vintage Christmas Card (ca. 1890–1907) by Edward Penfield. Original from The New York Public Library. Digitally enhanced by rawpixel

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