"Hole in My Shoe" is a song by English rock band Traffic which as a single release reached number 2 in the UK Singles Chart and number 22 in the German charts, in 1967. Composed by guitarist Dave Mason, it was disliked by the other three members of the group who felt that it did not represent the band's musical or lyrical style.

The brief monologue, over the mellotron passage, is spoken by Francine Heimann, the stepdaughter of Island Records' owner Chris Blackwell.

In the BBC sitcom The Young Ones, 'Neil', one of the principal characters, often sang a line from the song. Eventually, in July 1984, Nigel Planer who played Neil recorded a cover version of the song, which reached the same number 2 peak as the original. His version featured Barbara Gaskin on backing vocals and was produced by Dave Stewart, former keyboardist of Egg, National Health and Hatfield and the North (not to be confused with David A. Stewart of Eurythmics).

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