If I was just starting out again, I would spend the most money on good boots and the best clothing I could afford. Don't get me wrong, I've spent plenty of great days in the woods in a pair of Levi's and a hooded sweatshirt but being able to be comfortable when the weather sucks is probably the biggest key to success on any hunt that I've had. Nothing says "let's get the hell out of here" like wet feet and being cold/miserable.
