You know, Shannon, this does't surprise. me. As you know, I mainly dress quite casually for my work-at-home lifestyle. And it often feels...unstylish! It helps a lot when fit and colours are perfect. But especially in the summer, it can sometimes feel as if I'm not really getting properly dressed!
I do find that fall/winter - with their layering possibilities - seem to add more style-quotient to my own casual dressing. That's because it's easier to add that distinctive 3rd piece - be it a jacket, a scarf, a fine pair of boots - that just kicks it all up a notch - and yet not lose the casual flair. I have seen others do this in summer with great jewelry. But in our hot humid summers, I don't even want to wear jewelry! Plus, I don't own any great pieces that work for casual outfits.
I'm still mulling on this one myself.