I have posted about shorts before, I like them but it can be hard to wear shorts as a grown woman and not look, well, not silly but not exactly grown up either.
First off, and this might be obvious to some but I don't think it's obvious to enough people...stay away from short shorts. Yes, that's a period. Also, the "formal short" was a very bad idea.
Whether your shorts hid mid-thigh or graze the knee are more use and figure specific. the mid-thigh short I posted last week is great for a casual summer activity (I posted it for fruit picking). The knee grazing, fitted bermuda short in crisp black cotton or a khaki color can be 'dressed up' to look like more casual officewear, or fun out-on-the-town daywear. Vince shorts, or these Nanette Lepore versions are great -
These 7 for all Mankind denim shorts are also great -
The long short is a good look for pretty much anyone, and works with flip flops for the beach or a backyard BBQ (I chose this for a BBQ I had last weekend, it was perfect for when I was helping a 2 yr old eat watermelon and the juice was pouring onto my feet!) or you can wear nicer sandals and carry a nice bag and you will look a little more dressed up. Perfect for a summer day or evening.