Dark lipsticks are one of my favorite things, I probably have too many and I have no shame! They can dress up an outfit or give an edge to a very feminine flower dress. I am going to be very humble here (sarcastic) I have been blessed with great lips, but some people can struggle with dark lipsticks, so if that's the case, always use a lipliner first so it will make it easier for you to fill in with the lipstick and touch up any not-so-perfect lines.
When it comes to dark lipsticks I love matte ones from MAC or the Sephora lip tints (which last for hours!) and I pair them with a lip liner from wet n' wild or Essence. And if I want to add tons of drama and get some glossy finish I would go with a Dior lipgloss in a dark shade (it doesn't have to be the exact same color!)

Shop some dark colors: