is there any form of wear 2 3D items for the head at the same time?

No, one per body part.

Although there are in some cases where items have been combined as one, for example this cap.

http://forum.toribash.com/tori_shop_item.php?id=2113

yeah, but there is 1 stem, i had the idea of wear the swag cap whit the shutter shades

You would have to pay an admin and have an item forger do it as a custom item see Icky's shop here

yeah, that sound expensive af, but maybe when i have the money i Will try