I am red head, although not very dark. More of a strawberry blonde. I am also very fair with blue eyes.
Anyway, I where mauvish colour lipsticks, blue/grey eyeshadow and brown eye liner. I tend to wear lip gloss in pinks, not shocking pink as you are right, it can look odd. In fact all my lipsticks tend to be a lip gloss base. Another one I have is Clinique lip gloss. It's feels nice on.
I only wear cream blushes as I am not good with powder, it's usually an apricot sort of colour. I also have a mauve base cheek cream which works well. It's the Bobbi Brown brand. The eyeshadow I use is also a cream eyeshadow rather than powder...it's a Calvin Klein eye tint.
I wear a Mac foundation that covers up very well. It's called Mac Studio Fix fluid. Buy it on eBay.