Easy Casual

How easy casual is this Gap shirtdress? I got it this past weekend when I was home in Kentucky and love how it is so soft and easy to wear.  It's not like most shirt dresses that are all stiff and wrinkle badly.  

Here's an outtake but you can see my shoes, so I thought I'd include it.  Poor Miss P just so badly wants to be a dog model.  

I wore it with my brown leather Tory Burch Revas, which I admittedly sold about 2 months ago and then subsequently bought back because I realized that I would wear them a lot with my new job.  

My hair is a hot mess.  I am wearing it in braids or side buns almost every day.  I tried a lot of the tricks you all suggested and it still isn't holding curl worth a crap.  I think it's time to cut some inches off and get some more highlights.  I'm hoping the shorter hair will hold curl more and the highlights might damage my hair a bit to hold curl even better.