If red lipstick is a classic color, then consider the new crop of ultra-deep hues to be their punk rock-loving sisters. While not for the faint of heart, dark wine or brown hues give an otherwise tame ensemble some bad-girl edge, and make as big an impact as the traditional red. "To pull off this look, opt for lipsticks that are on the flatter, more matte side, rather than a shiny finish. You have to find the right balance," says makeup artist Jerry Johnson. "However, there are exceptions to the rule—darker lip colors can make small lip shapes look thinner, so I'd recommend applying a gloss just in the center of the lips to help them appear fuller." Still, the ever-trendy berry tone your BFF has stashed in her bag may not flatter your complexion as well, so we asked Johnson to break down the colors that work best for every complexion. Scroll down to find your perfect match.