In times past, "long hair" for women meant long enough to sit on. "Short hair" for men, therefore, could get shoulder-length or longer. Sailors and other wanderers who spend long weeks away from ladies and barbers often wore low ponytails to keep their hair out of their way.
Characters who sport a sailor's pony tail are not necessarily Long Haired Pretty Boys, as their lengthy locks are not flowing and feminine. The Sailor's Ponytail is visual shorthand that indicates an adventurous and down-and-dirty character — but not, like Wild Hair, a separation from society altogether.
(Except that longer hair for men was pretty universal in 17th century Europe, and by the early 18th century most men had begun to tie their hair back or wear a wig styled with a 'queue'. It's true that many sailors carried on wearing a long pigtail after short hair had come back into fashion.)
Further, an actor playing a character with a Sailor's Ponytail is often wearing a wig or hair extensions because it can take several months to well over a year for a man with a contemporary short hairstyle to grow their hair long enough for it to be tied into a ponytail. In Real Life, that would be why a man would keep it even in civilization; the intermediate stage, long enough to get into the way but too short to pull back, could be extremely awkward.
Ever-popular hair style and genre/setting indicator for the Wooden Ships and Iron Men.
- Pokémon Ranger and the Temple of the Sea is more sailing-oriented than the rest of the Pokémon films, and the movie-specific protagonist Jack Walker sports this kind of ponytail.
- Koyuki in Sgt. Frog 2nd movie sports a long ponytail since she's at sea with Natsumi, Fuyuki and her friends.
- Dietfried Bougainvillea from Violet Evergarden has one of these (Well, long braid rather than ponytail), even when on land. It seems he grew it in the navy then found that he liked it.
- Both the Pirate Captain and the Pirate with a Scarf have those in The Pirates! In an Adventure with Scientists. The Pirate Captain's ponytail is as luxuriant as his beard, the Pirate with a Scarf's is a lot shorter and somewhat scruffier.
- Jim Hawkins from Treasure Planet wears a ponytail. The film can be described as Treasure Island IN SPACE!. Jim is a boy searching for the treasure of the evil space pirate Flint.
- In The Princess Bride, The Dread Pirate Roberts wears a ponytail.
- Pirates of the Caribbean:
- Will Turner has a sailor's ponytail, along with other various pirates and sailors.
- When Elizabeth pulls a Sweet Polly Oliver, she noticeably keeps a shortened pony tail instead of chopping all her hair off.
- Most of the crew in Master and Commander keep their hair in short ponytails.
- Captain Smollett in Muppet Treasure Island has a white ponytail, which looks rather like a restrained version of the 18th century powdered wig. (And since he's Kermit the Frog, that's probably the most likely explanation.)
- Jackie from the Bloody Jack books initially cuts all of her hair off to pull off the Sweet Polly Oliver that gets the plot rolling. As she gets older, she grows her hair out into one of these, partly because it's expected of "young men" and partly so she can switch back into a girl when she wants to.
- Most of the sailor characters in The Liveship Traders, including the protagonist Althea, wear their hair this way as it's a fantasy version of Wooden Ships and Iron Men.
- The ballad "Faithless Sally Brown" is about a young man who's Press-Ganged and finds that his girlfriend didn't wait for him when he gets back. The penultimate verse mentions he "chew'd his pigtail till he died". Read the poem here.
- Roarke in the In Death series has longish hair which he normally wears loose, but when sitting down to do some intensive technical work he pulls it back in a stubby ponytail which the narration, via Eve's point of view, describes as making him look vaguely piratical.
- Mipps in the Doctor Syn ("The Scarecrow") series is a retired ship's carpenter who wears his hair in a tarred ponytail.
- In Rachel Griffin, Gaius is an example of the scruffy yet ready for action type; wearing his hair like this is one of the indications he is not quite the outcast loner Rachel initially assumes he is.
- Subverted in Farscape where the Peacekeepers have these as standard (perhaps because Space Is an Ocean) but the effect is totalitarian rather than rebel—Officer Aeryn Sun has to start Letting Her Hair Down once she's forced to join the Ragtag Bunch of Misfits.
- The vast majority of naval officers in Horatio Hornblower wear ponytails. Some lower-deck characters sport this hairstyle as well, but some of the hands have short hair.
- In Star Trek: The Next Generation, Klingon officer Worf of the Enterprise wears one of these starting in season 6's "Face of the Enemy". Fitting, given how (at least as far as the Federation's military culture is concerned) Space Is an Ocean.
- Guybrush Threepwood, protagonist of the Monkey Island games, wears a ponytail. He wants to be a pirate.
- Final Fantasy V's Sweet Pirate Oliver Faris Scherwiz wears her hair in a longer-than-normal version in the Yoshitaka Amano artwork.
- The titular Player Character of Pirate Hunter has his long blonde hair tied in a ponytail, and he's a Threepwood expy (though somewhat reimagined as a pirate-killing badass who takes plenty of names).
- Edward Kenway of Assassin's Creed IV: Black Flag keeps his hair in a low ponytail or, depending on outfit, a small bun and he is also a pirate.
- In Girl Genius, Airman Higgs ("The Unstoppable" Airshipman Higgs) wears one of these. As airship units are treated as analogous to naval ones (though seafaring definitely exists in this setting), it certainly qualifies as a Sailor's Ponytail.
- Dinty Doyle, a red-headed Irish sailor who is the main character of the Rankin/Bass special The Leprechauns' Christmas Gold, has one.
- Captain K'nuckles from The Marvelous Misadventures of Flapjack always (but rarely seen) sports a sailor's ponytail.
- PAW Patrol has Sid Swashbuckle, a pirate with a ponytail down just past his shoulderblades.
- Admiral Horatio Nelson's ponytail was cut off after his death at Trafalgar and preserved. It's on display at the National Maritime Museum.