For the most part when I wear skirts, I always tuck my shirt in. While there is really no right or wrong when it comes to tucking or not, there are a few guidelines to help you decide just how to style your tops. The most important thing to consider is the length of the top. If it is too short, it will not stay tucked in and will result in you having to fuss with it all day. If your top is on the long side and you are wearing a skirt, it is probably best to tuck it in or else it will completely cover your skirt, creating odd proportions. If your top is pretty long and you are wearing it with pants, there is probably too much fabric to try to tuck in. Make sure your pants have a skinny or straight leg, and wear your long shirts over top. Lastly, consider the fabric that your top is made of. Thicker fabrics or shirts that have buttons or other details are sometimes best to leave untucked because they will not lay right when tucked in. With the chambray shirt that I am wearing, it is a thicker fabric and a button down, so it is best to leave out of my tight pencil skirt.