late 14c., from tip (n.1) + toe (n.). As an adverb from 1590s; as a verb from 1630s. Related: Tiptoes (late 14c.), also tiptoon; tip-toed. Tippy-toes is from 1820.
Entries linking to tiptoe
tip n.1
c. 1400, "extreme end of something, top of something round or pointed, metal attachment to the end of something," from Middle Low German or Middle Dutch tip "utmost point, extremity, tip" (compare German zipfel, a diminutive formation); or from a Scandinavian source (compare Old Norse typpi).
toe n.
Old English ta "toe" (plural tan), contraction of *tahe (Mercian tahæ), from Proto-Germanic *taihwō(n) (source also of Old Norse ta, Old Frisian tane, Middle Dutch te, Dutch teen (perhaps originally a plural), Old High German zecha, German Zehe "toe"). Perhaps originally meaning "fingers" as well (many PIE languages still use one word to mean both fingers and toes), and thus from PIE root *deik- "to show."
Þo stode hii I-armed fram heued to þe ton. [Robert of Gloucester, "Chronicle," c. 1300]
The old plural survived regionally into Middle English as tan, ton. To be on (one's) toes "alert, eager" is recorded from 1921. To step on (someone's) toes in the figurative sense "give offense" is from late 14c. Toe-hold "support for the toe of a boot in climbing" is from 1880.