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Top 10 Pirate Flags

By Edited Nov 13, 2013 0 0

There are a lot of pirate flags out on the market for sale, available in  many imaginative designs, some replicating the original jolly rogers flown during the Golden Age of Piracy and some putting a modern spin on them. Below is a list of the 10 most popular pirate flags that you'll likely encounter.

10) The Crimson Pirate:

Crimson Pirate


Using a dried, bloody brick color for the field and dominated by a shrieking skull, which is seemingly impaled by two wicked cutlasses, this flag has a very "retro" feel. You might expect its design on the cover of a classic Choose Your Own Adventure novel or pulp magazine. 

9) Surrender the Booty

Surrender the Booty - Red

A classic double entendre, this one has a brighter, more eye-catching field that practically yells like a siren. The skull is more cartoonish, but also much more malevolent with the dagger clutched between its undead teeth and ratty tricorne decorating its head. 

8) Dead Men Tell No Tales

Dead Men Tell No Tales

This one lacks the character aspect of the last two, but possesses a better color palette. The blue highlighting really brings the white Jack Rackham design to life, almost causing the flag to glow. Its statement is certainly more ominous than "surrender the booty."

7) Time Flies When You're Having Rum

Time Flies(107967)

There's nothing complicated about this flag, but it's definitely the most lighthearted on  our list. Most people may not recognize the satire involved: the drinking skull and crossbones is taken directly from captain Henry Avery's jolly roger design.  A very suitable flag for rum-fueled houseboat parties.

6) Edward Teach (Blackbeard)


This design may appear strange to our modern eyes, as it lacks the skull and crossbones that have become so closely associated with pirates. However, many historical crews flew jolly rogers such as these. Death itself was often depicted as a demon holding an hourglass and stabbing at a symbol of man's mortality. This particular design was flown by none other than Blackbeard, whose real name was Edward Teach.

5) Brethren of the Coast

Brethren of the Coast

This flag, and its title, have strong implications of solidarity and rebellion. The Pirates  of the 17th and 18th centuries were often mutineers from the Royal Navy, men who suffered egregious working conditions for practically no pay. Contrary to popular depiction, piracy was a refuge and a chance at egalitarianism, not something that was readily available to most commoners.

4) Skull w/ Bandana

Skull with bandana

Well detailed, well dressed, and certainly jolly, this flag fills the popular niche that buccaneers have become in modern times. What child's costume is complete without a red bandana, gold earring, and eyepatch? More critically, the grotesque "happiness" of the skull brings out the comedy that is life, putting death in its place as a natural consequence of living.

3) Jack Rackham

Jack Rackham

This design should be recognizable. Its popularity proves that simplicity can be a more powerful trope, but more importantly, the design is historically accurate. Conceptualized by Captain Jack Rackham, it was the first of its kind, becoming a worldwide staple for depicting piracy and rebellion.

2) Classic Jolly Roger

Jolly Roger 2 Skull and Bones Pirate Pullover Hoodie Sweatshirt S-2XL Swords

Only slightly more popular than the beautiful simplicity of the classic Jack Rackham is the classic Jolly Roger,  which, of course, has received some modern embellishment in the form of an eye patch. Eye patches were actually worn for their utility in combat: the lower decks of wooden ships were very dark and transitioning down into them from the sun was problematic during battle. Having an eyepatch gave one an eye that was always adjusted to the darkness.

1) Deadman  


The number one most popular flag on Piratemerch.com, this one combines all the character from some of the earlier flags with the black and white simplicity of the Jolly Roger and Jack Rackham designs. Perhaps its most endearing quality is the subtle splash  of crimson on the knife. A truly terrific design that is worthy of its popularity.




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