When going for an afternoon jaunt, a WASP should still be aware of how they look! For my jaunts, I wear t-shirts with either my own or my dad's Alma mater. In addition, I always wear shorts that are a respectable length (just above the knee), and never-ever do I wear ghetto looking shorts that hang below my knees. Finish the look off with low top sneakers, and ankle biter socks. If you are interested in young ladies being willing to stop you and say hello, take a pooch with you as well. My boy never gets to run with me! The wife will not allow it......she knows me too well!