Alternative Apparel's "The Betty" hat comes in chic herringbone and plaid patterns, and the shape is actually flattering (like a really elegant baseball cap). I've never looked good in hats, but I think this one might actually be perfect to wear on a rainy day. Plus, it's on sale right now for only $12. I'm also contemplating purchasing the Madonna Slouch Pocket Tee ($28) with a great cut that reminds me of Alexander Wang's much more expensive version. The mustard yellow color is especially cute with faded jeans. Both of these items can be purchased on Alternative Apparel's website.
photo credits: http://www.alternativeapparel.com