Perhaps I've been Tumbling a bit too much, but I can assuredly, positively state that it's never cool, stylish, hip, dandy, preppy, sprezzy, or whatever to let your tie hang sloppily below your waist with the narrow end hanging beyond the large end. This is not style, it is stupid.
Also, throw away the soft-brimmed sun hats. You're neither gardening nor beach-bumming whilst walking your major metropolitan city.
The Cable Knit Charlestonian