Rule 1: Unless you're going for a patent leather-y bold lip color, always go with a sheer bright or dark gloss hue. Opaque bold glosses are nearly impossible to keep looking neat, and they create a more over-the-top look than most of us are going for. 
BMPRO's long lasting lipgloss looks good on everyone

Rule 2: If you buy a gloss that doesn't seem to mesh well with your skin tone, mix it with clear gloss or petroleum jelly to make it more wearable. ".

Rule #3: If you have fine lines around your mouth, choose a gloss shade that's "close to your skin tone. This will make any bleeding that occurs with gloss less obvious.

Rule 4: Don't get caught with any icky gloss mouth. You know how some people seem to have a gloss/saliva combo collecting in the corners of their mouth and along the inside rim of their lips? We hope you're nodding. This can be prevented by exfoliating lips regularly. She uses the simple "Vaseline with a warm washcloth" trick to get rid of excess skin. If that doesn't solve the issue, carry Q-Tips with you to swipe the excess gloss/skin/saliva/whatever-it-is off the corners and inner rims of your mouth.

Rule 5: Protect your lips. "Wearing lip gloss is like wearing oil on your body," says Babaian, so you need to protect your lips with sunscreen. 

Rule 6: "Don't rub your lips together. It pushes the lip gloss outward so your lips no longer look finished."

Rule 7: Check out the BMPRO long lasting lipgloss collection HERE