Should we clip out elderly horse?

So I work with a older horse (he's 33). He has Cushings and his hair gets really really long in the winter even though we blanket him (it's truly unmanageable if we don't). Anyway since its spring time now he's begining to shed but because of the Cushings he holds onto the hair much longer than everyone else. Today it was 70 and he was a bit sweaty when I got the the barn. Its supposed to cool off for the rest of the week. I'm wondering if you think we should clip him. He's not going to be doing much if any work since he's so old. I don't want him to be uncomfortable now but then again I don't want to clip him if its going to get cold again. Plus I'm not very good at it.... What would you do?