What do your undertones look like? Cool or warm? I love those Color Me Beautiful type books on your best colors (even if I don't always follow the rules). Sounds like you would be a Winter or an Autumn depending on your undertone.
It sounds like you have dark hair and darker skin so you will probably look best in black or deep browns, depending on your undertone (black for cool undertone and brown for warm undertone).
I have found that regardless of your undertone winter and autumns can usually cross over to the warmer or cooler colors as long as you pick deep colors. They are not quite as flattering but they won't make your skin and hair look off. For example if you have a cool undertone you can wear darker shades like chocolate brown just fine but you may find a light shade like warm caramel brown won't look right.
With the darker hair you probably look best in really dark colors (i.e., black, brown, navy) and may be able to pull off really light colors (i.e., baby pink, ice blue). You will probably find medium tone colors hard to pull off (i.e., peach, camel). If you have a light undertone you could also pull off a rose brown (it's one of the few cool browns - deep pinkish brown) and it should be as flattering as black.
I have almost black hair with red undertones and warm olive skin. I find all browns really flattering. My DH has almost black hair, olive skin, but a cool undertone and he looks better in black. He wanted a caramel (medium) brown jacket and it washed him out. He looks fine in dark brown. I have a similar reaction when I wear gray but I can wear black just fine (but brown is more flattering).
If the jacket and shoes you're looking at are a deep brown it sounds like it will look fine on you.
Hope that helps...
and R1ta, I have a similar coloring as you and I love wearing chocolate brown.
