escargot and freaky - I'm wondering if a dark red with no purple undertones would be better on you. The Revlon lip butter in Red Velvet is a good one, as is the dark red in the L'Oreal serum lipstick range (forget the name sorry) and the darkest red in The Body Shop's lipstick. NYX also does some good dark reds, google for swatches, and there is of course MAC too (see Temptalia for MAC swatches). Not a vampy colour, but just a red that's had the volume turned down if that makes sense? Like, if you have red in the colour chooser on MS Paint or another colour programme (sorry if this is a truly weird metaphor lol), you would go down from red into black rather than to the side and down into burgundy/purple? A blackened red basically, not gothy but just toned down from a bright scarlet.
Does any of that make sense? It also might be worth checking that you have a cool skintone and not a neutral one. I have a neutral skintone and my skin is a very pale beige rather than pink based or yellow based (in line with a very pale East Asian skintone). Pale olive skins can also be neutral - and yes, pale olive skins do exist! Olive skin doesn't mean dark but is about green undertones in the skin.
giveme what I think of as preppy style at least is very clean-cut, American, Ralph Lauren and J Crew type clothing, also Land's End. The kind of thing Michelle Obama would wear. Also re teal, teal is a warm colour - it's a yellowed blue. Cool-toned winters (aka most winters, just not neutral weirdoes like me 
) need a cool blue, and a green with more blue than yellow eg emerald, pine. Ideally a winter dark green/pine would just be a darker/blackened emerald iyswim. I actually find it quite hard to find a cool pine green, it's quite often a dark teal that's heavy on the yellow. Bottle or british racing green might be easier to find.