In my experience -
Ferragamo loafers - very comfy out of the box, but not best suited to suits. Pardon the pun.
Loading Derbys - very UNcomfy out of the box - need to be broken in. Was fine after about a month. Works with a suit.
Bruno Magi Derbys - very comfy out of the box and work with suits. People here go back and forth on their longevity but almost everyone agrees that Bruno Magli has one of the softest leathers around.