outlook

An old verb mostly at home in its participle. Samuel Purchas (1622) writes of a tower "battailed for out-looking artillerie", and Henry van Dyke (1895) offers rooms "outlooking on the piazza". It takes on or upon for what is faced. Holinshed (1577) still writes it as two words, "out looke". In modern prose it reads as archaic and literary, so keep it for deliberately old-fashioned description of buildings and windows.

Here out- means "beat at", as in its synonym outstare: to outlook someone is to win the contest of looking. Shakespeare's King John stretches it to "outlook conquest", facing victory down. In Chapman's Iliad, warriors strive to "outlooke" one another. Thomas Miller still uses it in 1838. The verb is archaic, so a modern stare-down is better called outstaring or facing down.

The same competitive out- as in the staring-down verb, applied to looks rather than gaze. It turns up in private writing: Mary Delany's letter of 1731 says nobody's equipage outlooked hers, Hester Piozzi notes that Sally "outlooked her sister", and B. F. Taylor's diary of 1862 has Burnside outlooking his chief on horseback. It is obsolete, so a modern reader would likely mistake it for a stare-down.

A working verb for checking gear. Charles Cotton's "The Angler's Ballad" (1689) urges fishermen "All your Tackle out look", meaning go over the tackle and pick what is needed. The words are split and inverted for the rhyme, so it reads almost like a phrase verb turned around. The sense is obsolete. In modern English it would be taken for one of the looking senses, so it survives only in reading older texts.

Seeing past something, and easily made figurative. John Yalden's Compendium Politicum (1680) doubts that two minds could ever "never out-look the Horizon of their reciprocal Interest". There, looking beyond a horizon means thinking past one's own concerns. The object is whatever limits sight, a wall or a horizon. The verb is obsolete, so modern writing would say look beyond or see past.