I’ve always regarded the plum lip and eyeliner look with great pause. The images conjure 1990’s trends of awfully rimmed lips, house parties, and some kind of early Aaliyah, chola/gangsta girl style many of us tried in our teens. So I was a bit taken aback at the sudden rise in the dark lip that I’d seen popping up everywhere, with Gabby Union reminding me of the look on the Oscar’s red carpet.
It came off as a little demure, a little sexy, and maybe even a bit  – charming! What I’ve noticed is that the look is best accomplished with a dramatically dark lip, richly done mascary, and a dewy cheek and face. Anything more would be a bit gangsta.

Three great options for the plum lip. From left to right: Mac Heroine, $16; Iman “Opal” $10; Motives for LaLa in Venti, $16
Plum lip inspiration: