Crossword clues for the word: SHOELESS The word SHOELESS has appeared as an answer to at least 7 crossword clues on different crossword puzzles. Crossword clues for SHOELESS Showing 1 to 7 of 7 results Clue(s) "Barefoot, perhaps" 68 Discalced Discalced. In one's bare feet Joe Jackson epithet Like baseball's Jackson Like Fred Flintstone, sartorially