I think you overthink things.
Why do you think everything has a meaning? Probably the graphic designer of the game didn´t even thought in all those things. Maybe he forgot that he had already used that model of bracelet in Jill. Maybe he uses those dresses just because he thinks they make the characters look good. For example, Jill is always dressed like if she were in a cocktail in the French embassy, black night dress, high heels and all, even when she´s just studying at the library, and I´m pretty sure it´s just because the 3D designer wants she looks always "high class", and overdoes it. The HOTs are always dressed with extremely reveling dresses and high hells, the nerds dress always like "young Sheldom", including bow tie, the rich students with pinstripe suits... even if they all are just in class. In real life all of them, men and women, would probably dress for class at the university just jeans and a pullover or a t-shirt and confortable footwear. It´s just the dev thinks that those characters look better that way, even if it´s not the correct situation for a dress like that, and also helps to identify the archetype to which every character is assigned. Things like that doesn´t have an occult meaning.