I spent the last week in Napa with my family. We went wine tasting and to a few events at night. The entire time I felt over dressed – I definitely did not bring the right clothes. Napa is a very laid back, casual place. People there just do not dress and jeans are appropriate everywhere. It is a nice break from worrying about what to wear every day in Chicago. I wish I would have been aware of this when I was packing! I wanted to share my mistakes to prevent anyone else from making them. The first night I had on black open toe booties with a high heel. They were a little too hard core for the occasion AND we were standing on grass the entire time so my heels kept sticking into the ground. I made a similar mistake the following night by wearing a black Fendi dress that was just too dark. Everyone had on prints and happy colors so I stuck out like a sore thumb. The last night we went to a party at one of the vineyards and I wore a blue leopard printed Stella McCartney dress with a little belt. Everyone else was super casual or in jeans. I highly doubt that anyone noticed or cared what I was wearing but it still bothers me!