It depends on the season and climate.
Right now it's winter and my lips can get dry very easily so i need lipsticks that are crazy moisturizing. My fav go tos are:
Revlon Super Lustrous in the Creme formula (these are AMAZING lipsticks for the price. I don't even always need a gloss on top and that is saying something. Tons of Mac dupes too if you look them up.)
Mac in Cremesheen formula
I also sometimes layer chapstick over or under a lipstick but this will break down the color (unless that's what you're looking for). So i prefer tinted chapsticks.
Revlon also just came out with some "Lip Butters" that are supposed to be a perfect in between chapstick - lipstick formula. I haven't tried them yet but i plan to soon.
ETA: As for longest last formula -- it really depends on you. What you eat/drink that day etc. But you can always apply lipstick, put a piece of tissue on your lips, apply power over top tissue, toss tissue and then reapply lipstick and that will make your lipstick last longer and work as a stain.