This sweet-meets-funky top pulls double duty: wear Derek Lam’s halter with a jacket and you’re professional and chic; whip off the blazer, and you’re looking sexy and provocative. The bow on this otherwise crisp stretch-cotton top is so exaggerated that it can’t be cutesy. It’s feminine with a confident streak that’s as big as its bow. Pull on a pair of slim-fitted pants, and you are ready for a hot date. But make sure it’s not your first! Wearing a piece of clothing this bold and precious will suggest you’re offering yourself too easily, wrapped up with a big bow and all. And while you’re definitely a gift to be treasured, it takes more work than yanking a ribbon to win you over! At Saks Fifth Avenue for $550.

Pair with: A top like this deserves the spotlight and the pants (a skirt would be too femme) should be understated and unadorned. Like T by Alexander Wang’s black stretch cotton and modal blend cropped trousers. On Net-a-Porter for $550.