"Although historically the tailor is the cutter, in the trade the 'tailor' is the man who sews or makes up what the 'cutter' has shaped." [OED]
The verb is recorded from 1662; fig. sense of "to design (something) to suit needs" is attested from 1942. Tailor-made first recorded 1832 (in a fig. sense); originally "heavy and plain," as of women's garments made by a tailor rather than a dress-maker.