Court Jester?

This dress I really like but it challenges me.  I feel it is too short for the classroom, so I wore this week on a day I just have office hours.  I also wore it with leggings.  It is somewhat see through and the leggings make me feel like I don't need a slip, which was good as I don't have the right length slip for this dress (yet another sign probably too short).  I am not sure it is the most flattering look on me.

And on the car ride to work I looked down and felt like the pattern was very court jester like.  But it feels like pajamas.....maybe it is the comfort that draws me to this item?