1860, "a type of long, flat-bottomed sailboat, American English, from sharp (adj.) + -ie. Meaning "slicker, clever person" is by 1942 (see sharper).
Entries linking to sharpie
sharp adj.
Old English scearp "having a cutting edge; pointed; intellectually acute, active, shrewd; keen (of senses); severe; biting, bitter (of tastes)," from Proto-Germanic *skarpaz, literally "cutting" (source also of Old Saxon scarp, Old Norse skarpr, Old Frisian skerp, Dutch scherp, German scharf "sharp"), from PIE root *sker- (1) "to cut" (source also of Lettish skarbs "sharp," Middle Irish cerb "cutting").
The figurative meaning "acute or penetrating in intellect or perception" was in Old English; hence "keenly alive to one's own interests, quick to take advantage" (1690s). Of words or talk, "cutting, sarcastic," from early 13c. Meaning "distinct in contour" is from 1670s. The musical meaning "half step above (a given tone)" is from 1570s. Meaning "stylish" is from 1944, hepster slang, from earlier general slang sense of "excellent" (1940). Phrase sharp as a tack first recorded 1912 (sharp as a needle has been around since Old English). Sharp-shinned attested from 1704 of persons, 1813 of hawks.
-ie
alternative spelling of -y; now mostly of -y (3), but formerly of the others as well.
sharper n.
1560s, "one who sharpens or makes sharp," agent noun from obsolete verb sharp "to make sharp" (see sharp (adj.)). The meaning "swindler, one shrewd in making bargains" is from 1680s, probably a variant of sharker (see shark (n.)). The shortened form sharpie in this sense is by 1942 (also sharpster), at that time also probably involving the "sharply dressed" sense of the adjective.