A lot of women would agree with me that half the stress of dates is deciding what to wear. Whitney Port is one of my favorite fashion inspirations because she is always willing to take a risk while highlighting her assets.
In a daytime date, Whitney wore a simple dress that was eyecatching with color and kept everything simple. Not that I am any dating expert but in personal experience, guys get easily distracted so keep the accessories minimal. Urban Outfitters is a great place to find bright everyday dresses that can be dressed up or down.
While heels typically are the perfect date accessory it is best to keep them for night rather than daytime. Daytime dates may be a bit more playful and adventurous and last thing you need is a trip to the doctor in result of twisting your ankle. I love Whitney's short ankle boots, try something urban like Whitney or a simple sandal would be great too. I love Sam Edelman's Gigi sandal that comes in a array of colors and very comfortable.