Does lipstick have to "match" or "go with" with your hair?

I use an Orange.And i have Brown hair i really don't match any of my lipstick with the color of my hair.I just go with any color that would go on me :heart: .But i'm sure the pink can go well with brown/red.
 
A hair colour will only look good on you if it goes with your skin tone, and since the tone is the same, your lipstick should still be okay on you.
 
I noticed that when I used to dye my hair really bright blonde in 12th grade, I had to do my makeup a bit darker since I looked kind of washed out. Now that my hair is a dark blonde, I find that I wear less makeup and I can wear more shimmery pink lipstick colors.
 
I do believe it should compliment your colouring, which of course includes your hair. When I was a box redhead I went for autumny colours, and now that I'm back to natural (almost black) I use shimmery pinks and reddish tints.