Wear something that makes you feel good and that you are comfortable in. Accessories like hats are great for creating different looks without actually changing your entire outfit and are wonderful tools for adding a splash of colour to the images.
When Lennie was working in Weed he saw a lady in a red dress and wanted to touch the dress. Lennie would probably want to feel this red dress. @zahraangel hahah this person made an of mice and men reference aww