Thanks for the explanation, Parsley -- context is everything!
I have a personal aversion to orange because it's not a color that works on me, but I have set that aside and the orange jacket has totally grown on me. I think it works on you. I will reserve final judgment until I see the cobalt.
I am following your threads with particular interest because with my lifestyle I've had to develop the "casual yet polished and maybe a bit funky" and get that down pat. DH and I have an active social life, since I work at home (telecommute) when the day is over I'm craving social interaction so we go out and about. This is only going to increase now that the kids are off to college in a few weeks. I spend more on my "out and about after work" capsule than my work capsule. I don't know if this is your issue, but for weeknight going out I try to achieve the "I just came from work and swapped accessories to make it going-out appropriate" effect. That is my own sensitivity to the fact I work at home -- whereas the people we meet up with are coming from the office. Does that make sense?
I will stay tuned with interest!