Hats, slacks or skirts? Oh my

One vote so far for the pillbox style.  Now I am toying with the thought of using the taffeta to do a small brim across the front of the hat. It's always an option...  I was originally trying for a hat along the lines of a victorian riding hat.  You know, like this-

This hat is from RiverJunction.com and for only $60 is not a bad price at all. However it is brown on brown and wouldn't match my coat so well... Therein lies the problem. I have searched all over for a rust colored hat and found nothing so far that I liked. I figured if I made my own, there would be no issue about matching the colors which can sometimes be tricky beyond belief... Reds, greens and sometimes even black can be tough to match. Too light, too dark, light or dark undertones, too green, a hint of blue, too bright, too dull and do you see what I mean? Total PITA!

I have made the brim for my hat, I have yet to try putting it actually ON the hat. Then there is the task (or maybe chore) of getting just the right bend or curve to it. Finding flowers, ribbons, feathers, bows and other adornments, keeping with or even contrasting the fabric can cause its own amount of headaches and frustration and then there is the question of how much is too much. This partly because I am not all that into excess... I am not a bling person or one to overdo stuff. I like clean, simple and understated elegance. Then at the Darby over the weekend, I found out that yes, jeans are pretty much forbidden. Slacks or trousers are ok, but not recommended. So I emailed my mentor and asked "What then?" Skirts? Is length a factor? *eyeroll* I do have the fabric and now I have a pattern, so it's not really an issue, but still. There is a lot to this sometimes.  To think some people change their outfits for each event- not hard to rack up a substantial bill in the clothing category.