As I said before, if the goal is a professional look for the group, I would suggest same/similar uniforms. You each have a style that depicts your strengths, none of which (except Clementine) is security. Individually, you look professional, together, you are a mishmash.
With Clementine, as I said, her look lends itself to this work and she benefits from that gear. But if the rest dresses down in utilitarian gear, she will stand out, possibly as a leader or at least the primary contact for the group, visually. As this seems to be in conflict with her personality, that, as well as uniformity, would be a reason to buy gear.
Okay, so that should settle the matter, please post what your final purchase will be, if any, and modify your sheet to reflect it. Is O'Connor buying two set of clothes and paying for the gun, or three sets? if not, who is?