Staff members at Newport's Way Forward have braved the shave to raise money for the day centre.
Gail and Becky underwent the fundraising challenge this morning (Friday).
So far the pair have raised more than £700 — with donations still coming in.
It's the second time Gail has had her locks chopped, having also done so three years ago.
For Becky, braving the shave was a first. Speaking afterwards, she told Isle of Wight Radio:
"It feel liberated to be honest! I have had alopecia throughout my life and my hair has been falling out a fair bit recently so I said to Gail I wanted to shave it off. And she said I'll do it as well, to support me."
Gail said shaving her head again was "quite nice" and allows her to "save a fortune on shampoo".
Having already raised hundreds of pounds, the pair are aiming even higher.
Gail said:
"We've set a new target of £1,000. A lot of the stuff we buy for the sessions, like art groups and sports groups, we have to fundraise for that to get the bits and pieces in.
"We'll put it towards a Christmas party and a Halloween party — just fun things for the guys to do really."
So will we be seeing Gail brave the shave again in another three years' time? "Possibly", she says.
Way Forward provides support for Islanders with learning disabilities.
You can donate to the programme here.