Went out last night with the family to celebrate my younger sister's birthday. As you will notice, I love hats. A lot. Some people find wearing hats to be a bit "costumey." I think you just have to match it with the right pieces to avoid the costumey look! I really loved this outfit, and it was incredibly comfortable.
Hat: $5 Antique Shop
Blazer: $25 (sale) Body Central
Sweater: $12 WalMart (few years ago.)
Jeans: $30 (sale) Alloy
Shoes: $15 KMart (they are now listed at $20, but I got them several years ago.)