If I were a dude this is how I would dress. Honestly since I have a little bit of an inner tomboy this IS pretty close to how I dress on some days. I think men should dress manly, a little rugged, and classic. There should always be some sort of element of surprise or a special detail. And never look like you are trying too hard, but you should always make an effort to look good. That rule goes for both men and women. There is a certain ease to a look that isn't fussy or over thought. Style has to come naturally, it can very rarely be learned or forced. I know some guys with a great sense of personal style; Claude, Bradford, Josh, Daniel, Addison and my husband come to mind. I'm sure there are plenty more on that list that I'm forgetting.