Dad's birthday is coming up and I've decided that its time for him to finally get some new attire. Some background... He is 50 and single, 6'0", bald, with a medium build. He goes bike riding 20-50 miles almost daily. He is a workaholic, very professional and successful man in the alcohol industry. When dressing for events, meetings, etc. (work-related things), he looks great, and I can see a confidence change as well. I'm trying to re-ignite that confidence change with some everyday clothes as well. His casual, non-work clothes, are simply whatever is on sale, or random cheap stuff from say, Wal-Mart or Target. Which is fine, for lounging around the house or doing yardwork. But from time to time, he does go out and socialize (something I'm also helping with), or even when out running errands... he needs something nicer! The Wrangler jeans and athletic T's need to stay at home. So with that said, how the hell do I dress a 50-year old man? He's clearly not into the same styles as me (I'm 20), nor can I see him wearing raw denim. He's not real into any bar or club scenes (thank god), but could simply use some nicer, casual clothes. What do I get him? I was thinking something along the lines of Banana Republic for some good shirts. Maybe even jeans. It doesn't have to be super expensive, just better than what he's currently got.