'cheerless' is formed in Modern English from the noun 'cheer' plus the suffix '-less'. 'cheer' originates from Old French 'chere', where 'chere' meant 'face, countenance, mood'. The suffix '-less' comes from Old English 'lēas' meaning 'without'.

'cheer' passed from Old French 'chere' into Middle English as 'chere' and later became the Modern English 'cheer'; the suffix '-less' comes from Old English 'lēas', and the combination produced the adjective 'cheerless' in Modern English.

Originally 'chere' referred to 'face' or 'expression' and then shifted toward 'mood' or 'encouragement'; 'cheerless' developed the specific meaning 'without cheer' or 'gloomy' in modern usage.