Aside from giving us serious eyebrow envy, Joan Smalls is wearing the hell out of that slightly red brown lipstick. (Side note: smize goals.) Outline your lips and fill them in with Charlotte Tilbury Lip Cheat Re-Shape and Re-Size Lip Liner, $22, in Foxy Brown and top it off with her Matte Revolution Lipstick, $32, in Very Victoria for a look that's defined and will last all day.

Photo via @joansmalls

Next time you think about wearing your LBD with red lipstick, don't. Katie Holmes' slightly glossy, red-toned brown is infinitely cooler. Try BareEscentuals Marvelous Moxie Lipstick, $18, in Rise Up, a buttery, superpigmented brown that gives lips a hint of red satin finish.

Angela Basset slays with her smoky eye/brown lipstick combo (seriously, we're #dead, this looks so good). Try a milk chocolate shade like Bobbi Brown Sheer Lip Color, $27, in Bobbi. (Side note: Bobbi's first lipstick color was brown, so she's definitely an expert.)

Pro tip: Bobbi Brown's resident editorial makeup artist Cassandra Garcia says if you're afraid of brown lipstick, a sheer lip color, as the color payoff won't be as intense. "Brown lip color is the perfect finishing touch that complements, rather than competes with, the rest of your beauty look," she explains. "It's a quick way to look polished and modern."

Ease your way into the brown lipstick trend by choosing a shade that has pink and honey undertones, like Hourglass Femme Nude Lip Stylo, $30, in Nude No. 6. We love the mauve brown chubby pencil because the formula is incredibly easy to apply and requires minimal touch ups throughout the day (because you know if you're wearing brown lipstick, it better look #flawless).

"Brown lips look amazing against matte skin and an eye bathed in warm neutrals," says Stapleton. The evidence: Shay Mitchell. Try M.A.C. Lipstick, $20, in Film Noir to get her vampy, reddish-brown shade.