In short, I'm pretty terrible at it.
I feel of all the color products we wear, it's the one that has the least flexibility. The range of non-crazy looking shades for me feels small and I still haven't completely wrapped my head around what a color will look like once it's on my lips.
Warm, subdued colors seem to be safest and work fairly well, but they also feel pretty boring to me. I want some more excitement! But then I buy a bold color and get freaked out over how stinkin' dark it is when on my face. My lips are a fairly good sized feature, I feel like they will usually make colors darker/brighter than I am expecting. On the other side of that, using something with heavy frost or is on the lighter side of the spectrum - I feel crazier still. Like I'm reliving some strange 80s nightmare. :)
So I have this tub of lip products that I struggle to use. Gloss is always low-risk, but I dislike the upkeep when I'm at work sipping coffee all day. I know part of it is just getting my brain used to seeing my lips in those darker/brighter shades, but I'm finding it even more difficult than getting used to having darker eyebrows.
My go-to safe items are L'Oreal Colour Riche in Fairest Nude, Rimmel Lasting Finish in Airy Fairy and my new happy discovery of NYX in Orange Soda. I tried out this afternoon dabbing in lightly then rubbing in to give a more stained effect with my Revlon Super Lustrous in Kiss Me Coral. It's a miserable combination with the CARGO eye look but, oh well. I'll try to remember before wandering outside.
I need to plan a tame eye look for tomorrow maybe so I can go for the Kiss Me Coral to work. Maybe I'll give those crazy Maybelline Cool Shadow/Liners a go on the lid and see how they last. When applying they do feel wet/cool, it's very odd. It looks like they may be discontinued (again? Makeup Alley reviews sounded like they've come and gone a couple times) and I can't say I would be too surprised with the odd application feeling.
Crazy clown lips unite!