What ever color looks best on me after you kiss my cheek ;D... Honestly natural colors natural tones look great on women. It also depends on a woman's outfit, if you are wearing dark colors you can wear a bright color to focus the attention on your lips and face. If you are wearing light colors a darker lip tone can balance it out, light lipstick on a light color outfit can portray a pale over all look. The same if the outfit was dark and the lips were dark too the outfit would portray a darker sinister look. Because your eyes are light, vivid colors can look great to. References: I apply logic to life
Normally I would not vote for deep red lipstick. It's too pertinent. But looking at your profile pic, since your lips are fairly small compared to the rest of your face it actually look good on you. I would say the red for occasions and nude.for everyday use.
You also have to keep in mind your skin tone. I have dark reddish-black hair and (very) pale olive skin, and can easily wear dark reddish browns and reddish plums (day or night). However I prefer lip TINTS (vs lipsticks) because they give you that 'pop' of color without looking overdone.
If you browse on etsy.com and type in 'organic lip tint' [in search] they have a lot of great options, all reasonably priced and made with safe, natural ingredients. Some sellers can even customize colors for you.
I think red lipstick with red hair is amazing but that's not an everyday kind of thing. Have you ever tried the nude lips with a small amount of makeup? It's gorgeous and looks good with all hair colors. you should try!