I gravitate towards lipgloss, but I actually have more lipsticks than gloss (2 KVD, 1 WnW and 5 MAC lipsticks vs 1 lipgloss: Milani Brilliant Shine Lip Gloss in Bare Secret). I became more comfortable with lipsticks when I started lining my lips with MAC's Cork or Chestnut lip liners. Gloss is easier in a pinch when I need something to cover my lips.
Honestly, I love both. I always apply lip-gloss over the lipstick. If i have to choose only one among them then i would definitely choose lipstick. I am kind a crazy about lipstick and have a huge collection of them.
I prefer better lipistick because it stands out in time more. The difference between lipstick and lip gloss is that you can create different shades of lipstick by applying one color over the other to get the necessary or ideal shade.
It depends on my mood. Some days I feel so sweet enough to wear a shiny light pinkish lipgloss, but other days( most of them) I prefer intense lipstick, which stays in place for a looong time, strong colors from red to black! Because I think yours lips should show the world who you are and how you feel that moment or day.