Your new weekend uniform
First, wear a shirt that is denim-looking, but isn't a literal denim shirt. Chambray, faded, or denim-looking fabric will do. The jean shorts should be either a dark wash or very light wash; middle-of-the-line plan fabric can look too bland.
Add interest to the outfit by wearing shorts that are destructed or have some kind of detail. Make sure to keep the rest of the outfit simple. Basic jewelry and neutral make-up will keep you from looking like a rodeo clown. Booties or a neutral sandal will pair well this look. Most importantly, wear it with confidence! People will admire your awesome look when you are confidently strolling down the street.