Crossword clues for the word: OLDSHOE The word OLDSHOE has appeared as an answer to at least 11 crossword clues on different crossword puzzles. Crossword clues for OLDSHOE Showing 1 to 11 of 11 results Clue(s) "Comfortably familiar person, informally" "Part of a pair for gardening, perhaps" "Something comfortable, so to speak" Comfortable thing Comfortable: Colloq. Part of a comfort simile Projectile aimed at a yowling cat Something comfortable Something comfortably familiar Something unpretentiously familiar Symbol of comfort.