Depends on how much of a sweaty betty he becomes! What work is he in atm, and how much does he sweat?
I'd start off with a very small clip or something, and if he carries on sweating, try "up-grading" the clip.
My 9 year old has never been clipped before either, so this will be his first year!!! I am starting off with a low neck and bib (chest) clip and see how we go. I would rather do that in the first go because it will only take 10 mins to clip and gives him a chance to get used to it without him getting bored and figety...so we can take more off later if needs be.
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well he will be competeing and hunting in the winter at the mo he is mainly schooling and jumping and is not too sweaty
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Then I would leave it until he starts that type of work, and see if he does get sweaty. If he is in medium/hard work, he probably will, but all horses are different!