1400-50; late ME prepositional phrase on less (also o less(e), earlier upon less) on a lesser footing or condition (than); first used as a preposition and conjunction in the early 16th century; see on, less
mid-15c., earlier onlesse, from on lesse (than) "on a less condition (than)," the first syllable originally on, but the negative connotation and the lack of stress changed it to un-.