Red lipstick for olive skin
I'm olive and I always wear Revlon's Spicy Cinnamon. It's one of my favorite red shades for golden olive to tan skin, it's really fresh and modern to wear,and you don't need much with it, maybe some lipliner.
Make Up Forever's lipsticks are pretty long lasting and now they have an even more intense formula which I imagine must really stay put a while.
They also have a nifty lipstick finder that pretty much does the work for you once you put in your information:
You can try a lip-stain as well and that way you can re-apply it with ease:
Shiseido's automatic lip crayon in LC4:
NARS Velvet matte lip pencil: check out Cruella or Dragon Girl
Hope that helps!
Makeup Forever 8 Matt
I have olive skin too, and I am quite picky with my reds. I found this red last year and it was life changing.
You will LOOOVE it!
I bought Yves Saint Laurent Pur couture lipstick in blood red and its amazing! I have the same skin tone as you and it looks lovely while staying on because it's a matte lipstick. It hydrates as well so you don't need a gloss on top or chapstick underneath. It's pricey but worth every penny!!!!!!!
Kat Von D's Painted Love Lipstick comes in a great red called Hellbent and you can take a look at the shade at: http://www.sephora.com/browse/product.jhtml?id=P21
Kat Von D's Painted Love Lipgloss has the same beautiful red shade as the lipstick (Hellbent) and it looks great over the lipstick and I think helps it to stay on longer. You can find it at: http://www.sephora.com/browse/product.jhtml?id=P25
What I do to help my lipstick stay on longer is I apply a thin layer of my liquid foundation on my lips and let it dry. I apply a thin layer of setting powder over my lips next and then I apply my lipstick. I blot my lipstick and hold a tissue up to my lips and apply another coat of setting powder through the tissue onto my lipstick and then apply a second coat of lipstick. It sounds like a lot of work, but it's really not. And once you see how great it works at keeping your lipstick in place I think you'll see that it's worth it.
I hope this helps you.