I’ve got a Katy Perry concert tonight, and since I’m going straight from work and don’t really feel like changing, I wear my concert outfit to work — this comfy motorcycle jacket and my favorite strappy heels. I’ll be out pretty late, and I know we’ll be dancing all night, so an updo is a must.

Boss says: “The red lip is a nice, sophisticated touch, but the leather jacket doesn’t really say ‘office’ to me. It’s not totally unprofessional, but it looks kind of dated.”