While trends come and go, some things truly stand the test of time. But when a classic meets a trendy twist, that’s where the style magic really happens. Take checkerboard, for example. The timeless pattern of contrasting squares has never really gone out of style (and everyone from Gwyneth Paltrow to Nate Berkus and Jeremiah Brent loves it). But as you can see from this year’s Small/Cool NYC, some fresh takes never hurt.