Michelle Williams Wearing a Dress and Sneakers

While Michelle Williams palled around NYC with her funny guy, Jason Segel, we couldn't help but notice that the actress was trying out one of our favorite styling tricks. With a Carven photo-print sheath on, Michelle Williams already had the makings of a cool look, but her high-top kicks took it to the next level of street chic. Consider this the living proof that a sporty counterpart to your favorite dress can have a pretty awesome effect — and requires minimal effort. In this case, look to a bold-print day dress and low-key kicks to channel Michelle's effortless day wear, then be sure to check out our tips to style up any of your dresses with sneakers for maximum cool.