A little late to this thread. My top 5 list is a bit more formal but here it goes:
(1) Really good shoes (the first thing people notice)
(2) Leather bag / briefcase (I cringe when I see attorneys / businessmen wearing laptop bags)
(3) Watch (wear a respectable watch - does not have to be too expensive - or don't wear one at all)
(4) Suit (if you buy suits off the rack, please take them to a tailor!)
(5) Pocket square (takes your suit / jacket to a whole new level;...