Unlike the original, Corneo will always choose Cloud ('the big boned girl') regardless of the dress the characters end up wearing, so Trophies aside, this is a purely aesthetic choice.

How do I get Don Corneo to choose Cloud FF7 original?

If Cloud obtains all of the highest grade items (a silk dress, a diamond tiara, a blonde wig, and sexy cologne) Corneo will choose him. The quality of the make-up work Cloud can have done is random, and the Bikini Briefs and Lingerie key items do not affect the value at all. Tifa is Don's default choice.

How do I get Corneo to pick Cloud in FF7?

When in there, go up stairs and to the left to find Tifa. You will have a conversation and then be told to go see the Don. Leave the room and you will go in to see him and he will pick who he wants. If he picks Cloud then the trophy should unlock when you enter his room.