I usually wear jeans, and a Tshirt ( Usually a black Dickies pocket Tshirt) short boots, and Sunglasses, (during the day) however, the puppy chewed my Oakleys up last year, so I've been making do by wearing a woolen slouch cap ( In New England it's referred to as a Scally) that I tend to pull kinda low over my eyes. During the Summer, the Jeans give way to cotton Cargo Shorts. During the Winter, I usually wear a button down leather jacket, sometimes augmented with a dark hoodie or a fleece depending on the weather.
I really try to stay away from really trendy clothing. I usually make a effort to make myself not stick out, that much, but I think that the Scally kinda advertises that 'I'm not from here', which is fine by me. For the most part, I make an effort to blend in and not call too much attention to myself.