Leighton Meester
Credit: Giovanni Rufino/TheCW

The Gossip Girl characters sure know how to work hard and play harder. But this week, Chuck must choose one—business or pleasure. Meanwhile, Blair looks to Nate for help impressing her boss and Damien continues his usual trouble-making. And how is Blair—shown here wearing an Alberta Ferretti cardigan, Oscar de la Renta blouse and Bensoni skirt—doing at her magazine internship? You'll just have to tune in to the CW Monday at 9/8c to find out. Click through to see this week's wardrobe!