Brand doesn't matter if the size isn't right. A good fitting $20 shift will feel better than a $100 one that fits wrong. Obviously, a $100 well fitting shirt feels great!
I'm a big fan of Land's Ends right now. Shirts aren't a much of a problem for me as pants. I need 35 1/5" inseam and no one locally stocks more than 34". I can get almost everything custom hemmed. The Vintage Khaki's are super soft. Anyway, check out their shirts. You can order from in stock selection (like 17x33 or 16.5x32) or custom order for exact fit. Go through the custom order to get descriptions of everything.
