c. 1300, originally comparative of up (adj.). Similar formation in Middle Dutch upper, Dutch opper, Low German upper, Norwegian yppare.
Upper hand "advantage" is late 15c., perhaps from wrestling (get the over-hand in the same sense is from early 14c.); lower hand "condition of having lost or failed to win superiority" (1690s) is rare. Upperclassman is recorded from 1871. Upper crust is attested from mid-15c. in reference to the top crust of a loaf of bread, 1836 in reference to society. Upper middle class (adj.) is recorded from 1835. Upper ten thousand (1844) was common mid-19c. for "wealthier and more aristocratic part of a large community;" hence uppertendom.
-most
superlative suffix of adjectives and adverbs, Middle English alteration (by influence of unrelated most) of Old English -mest, a double superlative, from -mo, -ma (cognate with Latin -mus; compare Old English forma "first," meduma "midmost") + superlative ending -est. Now generally mistaken as a suffixal form of most.