Notable Partners: Jennifer Esposito, Isabella Brewster, Renée Zellweger, Olivia Wilde, Jennifer Lopez, Zoe Saldana

With his ever-rising star in Hollywood so too has Cooper's propensity to stay casual grown, especially in the winter when he completes his cypher with fly ass topcoats. When he does "dress down" though, he favors dope semi-casual looks like this killer bomber jacket pictured above.