So to get Amy's special orange dress, you have to complete Amy's Max Love Quest.
Part of this is you talk to Jennifer about making a dress for Amy, and then you play poker with Jennifer and if you win her she will give you the dress to give to Amy.
However, from your images you supplied... it can be seen you have Amy's special dress without playing Jennifer at poker and have completed a scene with Amy wearing it. A big thing which I and many other state ALOT is DO NOT CHEAT DURING AMY'S MAX LOVE QUEST. Which way you did this, either by companion mod or cheat code is not that important, but it means you will be unable to complete that Poker Appointment with Jennifer.
If you have a save game before you did this then that would be best to go back and follow the quest.
I do not know a way to force this scene, and even if I did it you would be forcing things more out of order which could affect data stored in the game, and even, as we say, bork your save file.