“Sailor” has definitions beyond “one who sails,” whether that be one who sails for fun, for sport, for the navy, or for commercial vessels. “Sailor” can also refer to a wide-brimmed hat…
a sailor-suit-type outfit (or in Sailor Moon, someone who wears a vaguely sailor-inspired outfit)…
a kind of low-key pretty butterfly…
an oddly-positioned brick in bricklaying…
…or a “seasickness-resistor,” in the phrases “good sailor” and “bad sailor.”
There are a bunch of colorful synonyms for sailor beyond the few already mentioned, including the dated mariner, seafarer, bluejacket (for naval sailors), sea-dog, oceanaut, swab, gob, jacky, and hand.
The reason sailor is spelled sailor is probably peer pressure from tailor. It used to be sailour, but back in the day, people were more inclined to use mariner.
An appropriate rhyme for sailor is whaler.
Here’s a silly spoonerism. When contemplating the various Sailor Moon characters as seen above—Sailor Mercury, Sailor Moon, and especially Sailor Venus with her dreams of a musical career—a new sailor-name occurred to me: Sailor Twift.
Here’s some sailor word art, courtesy of VectorStock:
Ambigram Bastian Pinnenberg designed a “sailor” ambigram as part of a “Sailor Moon” ambigram in 2010:
In a database of cryptic crossword clues, SAILOR is the answer ten times. The best clue is “Crew member said lord loses every day.” (Crew member is a sailor, and if SAID LORD loses every D (day), it becomes SAI LOR.)
Riddle answer: “The sound I will make always means yes when I speak, and see? What you just heard describes where I am…Who am I?” (I/aye, see/sea)
And finally, along those lines, sailor culture itself can be a wordplay theme. Sailing life has produced lots of special jargon that’s filtered into mainstream culture (batten down the hatches, even keel, fathoming, shot across the bow, three sheets to the wind—even let the cat out of the bag, which has nothing to do with felines). And there’s more specialized sailor-talk that’s not so familiar, which might be good grist for a puzzle.
Probing a single word like this has been intriguing. If you have any ideas for another word to cross-examine in this fashion, you can leave them in the comments or email replies!