While the Dior New Look fits Grace Kelly just fine, it can be a bit much for everyday wear more than half a century later. You can have the full silhouette from a skirt though, just as easily as with a dress. By picking separates though, you can find more of that tulle Kelly's character Tracy Lord so loved, and still keep things casual. An oversized, pastel sweater paired with laceless sneakers makes things much more the speed of a date at a coffee house instead of dancing with the Vanderbilts at their seaside home. This playful clutch is a subtle nod to the fact Tracy Lord gets three men to fall for her in the space of a few days, and might be some inspiration for your "to-do" list too!