I do the shopping and will usually tell him about at least one item that I've ordered and is on the way. He'll tell me when he wants something - certain category of toy - but usually it's a case of him giving me the thumbs up to order a specific item I told him about previously.
He's learning to speak up sooner or just say "yes" to my suggestions at the time I make them. There have been several occasions where he waited a month or two to give me the go ahead and regretted that he'd waited once the items arrived.
We shop together. Sometimes we browse on our own and then add them to the wishlist to share with each other later. We are fairly new to adding sex toys into our sex life so we think it is important to discuss it before ordering anything
Me (the she in our he/she relationship). I ask him for suggestions but he never really knows what to suggest. He always says he doesn't know what we could buy, or what sex stores sell, even when I tell him ideas!