Chapter 9 - You need this in order to obtain the trophy "Dressed to the Nines". Cloud has a total of 3 dresses. A black one, a blue/black, and a white one. There are conditions that need to be met in order for you to get each.
There are two possible routes for you to take, Madam M's and Chocobo Sam's. Doing all the side quests for Madam M will reward you the white dress. The blue dress on the otherhand, will be given to you if you finished all of Chocobo Sam's side quests. The black dress will be the default dress for cloud in case you only did one side quest in chapter 9.
Madam M's request: The Price of Thievery and Shears' Counterattack
Chocobo Sam's request: The Party Never Stops and A Dynamite Body
Madam M is a prideful woman who runs a massage parlor in the Wall Market in Final Fantasy VII Remake. Like Andrea Rhodea and Chocobo Sam, Madam M also possesses the rank of approving women to see Don Corneo.
Source: https://finalfantasy.fandom.com/wiki/Madam_M
Chocobo Sam is the owner of a chocobo stable in the Wall Market District in Final Fantasy VII Remake. He runs a successful delivery business called "Sam's Delivery," which employs chocobo-drawn carriages to cart goods and people around the Midgar slums that don't have proper road infrastructure like on topside. He is a seeker of thrills and gambles, and also a recommended agent for Don Corneo's bridal auditions.
Source: https://finalfantasy.fandom.com/wiki/Chocobo_Sam
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