It depends how fast his coat is growing, and whether he has a straight or curly coat. Will you be keeping your Portie in the traditional lion clip, or were you thinking of an all over trim? He will need grooming through to remove knots a couple of times a week, and will probably need bathing and clipping about every 8 weeks - possibly more frequently if he is to be shown. Are you planning to do this yourself, or to take him to a salon? Either way, I think they are better learning to get used to being groomed, and to the sound and feel of clippers, from the start. I haven't had a PWD, but I have had Löwchens, which have a quite similar trim. I used to clip my puppies out in lion trim at about 6 weeks - mainly for me to assess their outline, but also because it was the way potential owners expected them to look. I have to say that the majority of pet Löwchens are kept in a puppy trim - similar to the Portie Retriever trim. If your boy hasn't had a trim yet, I imagine that he might be tending to tangle by now and it might be good to have a light puppy trim for his first experience of visiting a salon.