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It should work for all suits costing $1000 and shoes at $200. My advice is keep reloading the game and buy another suit and go to packie's mission trigger. Also if you wear glasses the mission won't start. - Hope this helps!
Try the onyx suit and the black wingtip shoes which are both around the back of the store. I used them for the mission so i know they work. I was confused about which shoes were "smart".