I think if you mess around with the order you pick them up in, they will go to different hands.I'm not a fan of the way picking up and wielding items works at the moment, but it is doable if you spend enough time fiddling with it.
And of course, your person always wears bracelets, and earrings on the right side, and rings on the right thumb. Even if you wear more than one. You have to imagine that wearing ten rings on one finger gets kind of awkward, not to mention the terrible chiropractic problems cause by 100 rock earrings tilting your head to the side...Though I think Toady said something about fixing this in the next version.