Casual dates (especially during the day) can end up moving around the neighborhood, especially if they are going well. Things I love for a casual first date: Easy dresses, jeans with a chic top or blouse, dress with tennis shoes, non-jean shorts with a blouse, or a blazer with leather pants.

What should a guy wear on a casual date?

A collared shirt is almost always a must for a first date. Unless the two of you are off on a serious sporting adventure, wear a button-up shirt or polo. For a cozy dinner, choose a button-up shirt in a classic print, like windowpane or gingham.