Cllr Andrew Jenner is joining in with Movember, which asks men not to shave their moustaches for the whole of November to raise money and awareness about men's health issues.
The event originated in Australia and Cllr Jenner, who is half Australian, was keen to show his support.
He said: "Last year it raised about £92m across the world. It's just phenomenal and very important."
Cllr Jenner is not facing the challenge alone and has been joined by friends and family including son, Aaran, and daughter Kylie's boyfriend, Ed Leonard, in putting down the razor.
Anyone looking to sponsor the group can do so at Maidenhead Town Hall or Jenner's Cafe in Ray Mead Road.
Top Ten Articles
The Met Office has issued a yellow alert for Windsor and Maidenhead, Slough and Wokingham, warning that rain moving eastwards across the south of the country may turn to snow in some places.