This was an antithesis to Pink Floyd's "Another Brick In The Wall (part II)," in which Madness rejoiced in their school days. Frontman Suggs recalled in Uncut magazine March 2008: "'Baggy Trousers' was sort of an answer to Pink Floyd, even at that age I thought the line 'teacher leave the kids, alone' was a bit strange, sinister - though I think Floyd are a great band. It sounded self-indulgent to be going on how terrible schooldays had been; there was an inverted snobbery about it too. 'You went to a posh public school? You wanna try going to my school.'"

"Baggy Trousers" featured in the 2001 film Mean Machine, which starred Vinny Jones.

This was the third of 16 Madness pop promos directed by Dave Robinson, whose day job was their record label boss. It was filmed at Islip Street School, Kentish Town. Saxophonist Lee Thompson wore in the video 64-inch baggy trousers previously worn by the portly actor Peter Ustinov. When he played his saxophone solo he is shown flying through the air by means of a wire from a crane. Guitarist Chris Foreman recalled in the same Uncut interview: "One night Lee and I had bunked into see Genesis at Drury Lane - at a point in the set there was an explosion and Peter Gabriel went flying through the air. That's why Lee went flying in the 'Baggy Trousers' video-he always vowed that when he got the chance he'd do the same thing."

Suggs recalled to The Daily Mirror September 18, 2009: "I remember thinking that Pink Floyd's Another Brick in the Wall showed a very different school experience to ours. In my school, I generally felt sorry for the teachers who were given a hard time because we were all up to no good. So I tried to redress the balance a little bit with this song. The title refers to the high-waisted Oxford bags we used to wear with Kevin Keegan perms - the worst fashion known to humankind. It became so popular with primary school kids that it resulted in us doing a matinée tour."

This song represented the first time that Suggs took songwriting seriously. He recalled to Q magazine November 2012: "I was at Lee (Thompson)'s flat on the Caledonian Road in a sleeping bag on the floor, thinking about Ian Dury. I thought if I just wrote down all my memories of school, the wasted f---ing time and the fun, then tried to put them into some kind of rhythmic order… the mixture of happiness, sadness, pathos. That was 'Baggy Trousers 'and I thought, I'm on to something here."