I took inspiration for this from someone and I can't remember who but creds to whoever did this first. Also, naturally, I do not own any of these pics.
Luke:
The hoodie belonged to Luke at one point, and you very rightfully stole it.
mcquaid:
McQuaid actually picked out the shirt for you, and you now wear it non-stop.
tyler:
The T-Shirt once belonged to Tyler, and you stole it because it was comfy and smelt like him.
kate:
Kate always told you that someone needed to be the fashionable one. However, she helped you pick out the skitrt.
emaline:
This outfit was actually a gift from Emaline, and so you wear it as often as possible.
oliver:
It's mostly just the flannel, considering it once belonged to him. He loved when you wore his flannels.