Paul Naughton, head teacher of the Sacred Heart Catholic Primary School in Byermoor, is raising money for Macmillan Cancer Support.
He has been wearing shorts for six months now and tells Premier his family will not even let him wear leg warmers: "My children are very strict with me, I've tried some nights when it's been particularly cold and the heating's not been working well to maybe slide some pyjamas on - but they won't have it!
"I have to wear shorts to bed, so it's literally 24/7 shorts - it's getting tough."
The dad of three also said he had been getting some funny looks at church, around town and was the only person out of 55,000 spectators at a football match to be in shorts.
Mr Naughton told Premier at first staff were sceptical, but now everyone is on board: "We had OFSTED in school at the end of September, and when the OFSTED inspector came into school I was there to greet the person and they said to me 'can I speak with the head teacher?', I said 'I am the head teacher!' and I got a very long stare about that one."
He told Premier people often give money to a charity immediately but this is a slower process: "Initially people just saw you in shorts and that's fine, but as the months have gone on and the autumn's turned to winter you get more and more people looking at you and going 'what? why? why are you in shorts?'
"It's just beginning to get quite tough... the mornings and evenings are particularly difficult."
Listen to Premier's Hannah Tooley speak to Paul Naughton here: