1. Know your undertones. Do you have cool or warm undertones, are you more yellow tint or red? In MAC foundation are you an NC or NW? Knowing the answer to those questions will help you immensely on your search. Certain reds work with certain undertones.
2. Start cheap. I am a firm believer in practicing with lower end brands before you splurge on the expensive stuff. I don't know about you but I feel a LOT better about wasting 6 bucks over 32 bucks! Once you know what color works for you in lower end brands there is ALWAYS a higher end dupe.
3. Experiment with Finishes. This is totally preference but you might be surprised at how different a matte red looks on you rather than a glossy red. I'm a fan of both however I live for a non-drying matte lip.
4. HAVE FUN. I will say this until the cows come home, it's just makeup....have fun with it!! Seriously. Don't be scared to rock a red lip. No it's not reserved just for date night. I refuse to be put in a box like that. Have fun with your red lip and be fearless dolls!