I love it when a boot looks worn in. When on day one it already looks like your favorite boot that you have been wearing for ages. It gives that classic, not trying to hard kind of look.
This distressed boot by Stetson totally fits the bill. This boot gives off that classic, cool feel. The tough guy who tears up when his dog dies type feel. I like it paired with jeans, a plain tee and a button down worn open. Sleeves rolled up would complete the look for me.