Crossword clues for the word: CAITLYNJENNER The word CAITLYNJENNER has appeared as an answer to at least 3 crossword clues on different crossword puzzles. Crossword clues for CAITLYNJENNER Showing 1 to 3 of 3 results Clue(s) New celebrity of 2015 Transgender rights activist who was named Glamour Woman of the Year in 2015: 2 wds. Transgender track-and-field star who received the 2015 Arthur Ashe Courage Award: 2 wds.