Ms-nietzsche: Revlon just released a matte line of lipsticks, that are really nice. I just bought one on a whim the other day and they're very smooth, not drying but super matte and come in retro 40's and 50's reds (plus they're cheap) but you have to make sure your lips are well exfoliated, mattes show ever flake.
For me the reds that I've found that worked on my super pale neutral-borders on pink undertone skin and dirty blond hair:
Lancome: red stilleto (it looks different on everybody, it looks blue red on me but pinkish red on my friend)
Anna Sui: red #460, it's a brick red with a bit of gold in it.
Marcelle: ruby red, a dark 30's/40's red
Mac Mattene: you say tomato, an orange red.
I just dyed my hair a dark burgundy though so most of these don't work well anymore, they're too dark. I've switched to more of a bright 50's cherry red, revlon's matte strawberry suede and that looks much better.
To everyone who says they feel too clownish or uncomfortable wearing red, you should try a lip stain like benetint that will give your lips a natural rosey color. Either that or try a sheer red lipstick. Sometimes it takes easing into a bright lipcolor if you're used to more neutral one. A trick I learned at makeup school if you bought a red that you don't feel comfortable wearing is to put lip gloss on first then put the lipstick on, then gloss over it. It sheers it out and that way you don't waste it.