- "Why are you wearing that hat, Sir?"
"Because it's so hot, my holiday hat is really useful for keeping the sun off my face."
"That's a good idea, Sir. I take my hat off to you!"
- ―James and the Fat Controller
Holiday Hat is a magazine story.
The Fat Controller is going on holiday to Spain with his wife and grandchildren. The engines are worried about the railway, but realise that even the Fat Controller should have a holiday. However, there is a heatwave on Sodor when Sir Topham Hatt and his family arrive home and James does not recognise him as he is wearing a sombrero.
- Sir Topham Hatt
- Lady Hatt (does not speak)
- Bridget Hatt (does not speak)
- Stephen Hatt (does not speak)
- Bertie (does not speak)
- Thomas (cameo)
- Harold (cameo)
- Annie or Clarabel (possible cameo)
- A coach with a face that resembles Annie and Clarabel appears, however it is not confirmed whether it is them or not as they are not mentioned in the story and their nameplates are not visible.