I remember some of the ‘upmarket’ grammar schools having rules about day boys not visiting theatres, cinemas and similar places on week nights even with their parents. I also believe some schools had rules about boys going out with parents having to wear full school uniform even at weekends. I’m not sure if the same rules applied in the school holidays.
The rule about boys not wearing underpants under football shorts would be in line with the rules about no underpants under gym shorts. Presumably this was to ensure a complete change of clothing for sports activities.
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