Q: So my pop and I are having a debate which I hope you can clear up. For my 5 year anniversary my wife and I are going to dinner followed by the orchestra. I want to look like an MB so I though this is a great excuse to purchase a new suit, but my pop told me to go for 2 nice sport coats and pants as needed which would allow me to mix and match all year long. Makes sense, is he on point with this? Also, would this be acceptable wedding and funeral attire or is that where a suit would come in?
A: It sounds like you don't just want a suit but need a suit, so we're recommending you ignore your old man and buy a suit. Choose something slightly more casual and you can flip your pop's argument right around, i.e., match the suit pants all day long with a woven shirt or knit shirt or sweater, and match the suit jacket with denim. You'll save money (well, maybe) and have something to wear to weddings and funerals.