In my opinion, an oversized button-up shirt over black leggings is the new T-shirt and jeans. Maybe even a little more sophisticated than the jean/tee combo. It’s comfortable, cute, and casual. Add my favorite pair of riding boots and my sister’s funky chain necklace, and I’m ready to go. (Sorry sis, I’ll put it back.)

Boss says: “This is a fun way to keep a classic white button up looking modern and young, and the pulled-back hair and cat-eye show she put in a little effort. Even when she’s wearing something tight (like the black leggings), Chelsea knows what to wear so that it works (the oversized blouse). I would play around with the accessories more and maybe try out different shoes, but overall this is a good look for the office.”