Recently I had someone ask me how to make shorts a little more dressy. In this case it's all about the fabric. You don't want a nice pair of shorts that lose their luster as soon as you iron them. Look for a fabric that is going to keep its shape. The ones that I have on are 97% cotton 3% spandex which lets there be a little give in the fit but still be structured.
Another thing to really take into consideration is the length. No booty shorts in the office please. These Bermuda shorts are perfect to take from day to night. Adding a pretty heel with them will elongate your legs and make them perfect to wear to work and then for cocktails later. Also, don't be afraid to play with color!