I still feel like a relative newbie when it comes to wearing hats and I certainly don't wear them everyday. I don't have the confidence or the style to wear one like Jessica from Chronically Vintage (who has great taste and style for wearing hats), but I'm learning what I like and what works with my hair or how to wear my hair with a hat. I am wearing them more often this summer than ever before and more than just sun hats.
Much of my anxiety in the past about wearing hats has actually been less about worrying what others will think and more having to do with the fact that I didn't know what hat to wear where or how to fix my hair with them. Not to mention, that some of the most fabulous vintage hats call for a stupendous outfit and/or occasion for them and I don't have a lot of fancy clothes or fancy places to wear them. So, sometimes I would buy a hat that I just loved the looks of, but couldn't quite figure out how or where to wear them.