Ichabod Crane Pins and Buttons

Don't Lose Your Head

Trumpkin loses his head. Design by Sinister Fruit.

A cute little horseman!

The Hat Box Ghost from Haunted Mansion is riding a horse in the style of the Headless Horseman.

This fun illustration features the headless horseman, perfect for Halloween.

Don't lose it!

Sleepy Hollow fan art

Horse Man!

The Headless Horseman just wasn't as menacing when his horse was in the shop.

This year, strut around your private school is style. With this iconic shirt, you'll be sure to catch the attention of Katrina Van Tassel. You'll be the talk of the campus that's for sure. And don't forget—this shirt is also perfect for yachting, lawn tennis, croquet, binge drinking, questionable hookups, and bribing your way into the Ivies. Beware of Abraham "Brom Bones" Van Brunt though—he gets hotheaded when there is a few gin gimlets in him. He'll be jealous once he sees you in this shirt and is likely to do something rash. And definitely don't let ol' man Lauren see you donning this wear. He's likely to take away your scholarship.

Fan of the sleepy hollow legend then you'll like this Pub and Inn design as the headless horseman is drinking a beer on halloween eve. Drink up freaks!

Our version of the Death tarot card depicts characters found in "The Legend of Sleepy Hollow" by Washington Irving. Here, you'll see The Headless Horseman riding his horse of death toward the terrified Ichabod Crane as he pleads for mercy. His horse wears the traditional flag found in Rider-Waite’s Death tarot card. The white flower on this flag symbolizes purity and immortality, and it’s five petals represent change. In the background, you'll notice we've used two lofty, twisted trees in place of the traditional two towers. You will also see the moon instead of the sun as it rises over the horizon. The river serves as the boundary between this world and the next, and the ghostly ship sailing its waters escorting the dead to the ...

El jinete sin cabeza de Sleepy Hollow, en tres colores, blanco negro y rojo. Theprometeus 2023

The Headless Horseman in the Rat Fink style

Halloween design of two skeletons dancing. Caption reads Halloween is almost here. Let's do the Ichabod Bop.

Take it to the paint!

The Headless Horseman is out in the hunt of a head

Losing your head because the best time of the year is almost here? You bet you are and you're in good company. Wear the cabeza that ended Ichabod Crane! Wear it proudly. Just like he did.

Headless Horseman of Legend on a Rearing Black Horse

A quick design.

Retro comic design perfect for kids and adults who love skateboarding. Grab this design as a birthday or Halloween gift for your friend or family member who also loves the headless horseman. The design is also great for a Christmas present.

Headless Horseman finally got some new wheels!

the headless surfer

Visit Sleepy Hollow, you'll lose your head!

A quick design.

Please Book A Head

The Legend of Sleepy Hollow

Headless Horseman

The Headless Horseman, don't go venturing alone at Sleepy Hollow!

Trip Van Winkle and the Ichabod Gang

A spooky Halloween design of The Headless Horseman of Sleepy Hollow.

Aesthetic Alternative Movie Poster of Sleepy Hollow

Aesthetic Alternative Movie Poster of Sleepy Hollow

Aesthetic Alternative Movie Poster of Sleepy Hollow

Represent what you believe