I used to wear brown a lot in high school, but then I started to like black a lot more. Now I think I'm falling in love with brown again. I think it's a great color with my hair, skin, and eyes.
Have you ever figured out what your "color season" is? It's the idea that you can predict which colors look best on you, based on your hair and eye color, and your skin tone. Your group of most-flattering colors will be labeled as Winter, Spring, Summer or Autumn. Since I have auburn hair and pale skin, I should be an Autumn. Brown is definitely one of my prescribed colors. Black is not. But I really like how I look in black. What's going on with that?
I wondered about it this past winter and looked into the color season concept. I found several discussions that say that color seasons are a lot more complicated than just four seasons. If I were an absolute Autumn, I shouldn't look good in bright white or black. But I like how I look in both of those colors. I think white and black can make some redheads, especially strawberry blondes (those people whose hair is more like light orange) look washed out. But white and black are flattering on me. I found a guide to some more specific categories than just the four seasons: Light, Deep, Warm, Cool, Clear, and Soft. Now I know that I'm a Warm Autumn, and that adds some stronger colors to my recommendations (but still not black or white). It also seems that people can sort of flow between seasons, or be on the cusp between two seasons.
So, like everything in life, there might not be a super-simple answer to the question of which colors you should wear. The good news is, that means you can probably look great in more colors than the four-season typology holds. Try on whatever colors you like! Wear whatever makes you feel good! If there's a color you like, but it doesn't flatter you, and you don't want to wear it next to your face, try to find a purse, shoes, or belt in that color. Maybe you can find a multi-colored shirt that doesn't place the unflattering color right next to your face and hair. Another idea, for a color that just doesn't look good against your skin, is to wear pants or a skirt (with tights) in that color.
It's kind of fun to see which colors are recommended for you. There might be a few that you haven't tried before, and maybe you'll find a new favorite. I keep seeing lime green and orange as recommendations for me and I'm skeptical, but maybe I'll try on those colors the next time I'm out shopping. You never know...
This post from Into Mind can help you narrow down your season more specifically.