I’m halfway through the dare, and I think I’m getting the hang of it. I have a date with my boyfriend tonight, so I decide to wear his favorite outfit — my floral dress and riding boots. He always tells me how much he likes when my hair is pulled back, so I decided to do a headband braid with a romantic side chignon. (Click here to see what guys think about your favorite hairstyle). I’m worried that the dress might be a little too casual for the office, so I decided to put on a little more jewelry and add a belt to give it more structure.

Boss says: “The floral dress is a great look and I love how youthful Chelsea’s makeup and hair are. It shows plenty of effort and creative touches, though it would be it’s a little too casual for an interview (just something to keep in mind). Adding tights with the dress is a great way to make it more work-appropriate. I might ditch the hoop earrings though, they seem like overkill.”