Picture added by Super Grover
Deliberate mistake: Jack wears one pair of boots throughout the movie; however, the heel has at least two discernible heights, including the ones worn in the underwater close-up. One kind is worn by Tony Angelotti (Johnny Depp's stunt double) and the others are worn by Depp. When Jack steps onto the dock from the Jolly Mon and when he's balancing himself on Will's sword at the attempted hanging, he's wearing the higher heel boots. As Jack crawls across the broken mast chasing the monkey, and when he dives off the Pearl's plank, the lower heel boots are obvious. (01:34:40 - 02:06:30)Super Grover
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