"They key is not to stress out over it [getting your clothing just-right]. Whether it's a tie or a pair of shoes, they're just clothes after all. Enjoy the process of learning. If you could ever get a complete handle over your wardrobe, dressing would become formulaic and boring - Garanimals for adults. Over time you'll learn what tie width suits you best, how you like your shoes polished, the proper way for a lapel to roll, and a million other little things that become second nature faster than you'd think. And every time one thing becomes common sense, two new issues will pop up.
But that's why you can really enjoy your clothes - there's always something new. Don't worry about them. Enjoy thinking about them, doing research before purchases, living in the clothes you own, and avoid, at all costs, making the process seem like studying for an exam. Dressing is an ongoing process, and a thoroughly enjoyable one at that. Treat it as such."
This is such great advice. I remember when I first started to care about what I looked like--rather late in the game, I must admit. I felt like I had to catch up to those who had been listening to their dads' advice all those years. It was impossible. I ended up buy either the wrong thing, or nothing at all. It wasn't until I relaxed and realized I was going to get it wrong for quite awhile, but that, eventually, I would get something right, that I started to enjoy playing around with what I wore on a daily basis.
I think one of the worst things we can do is treat anyone's opinion as the gospel. Magazines like GQ and Esquire will drive you crazy--not only do they make you feel like you're doing "it" wrong; but "it" changes on a daily basis and you're left playing catch-up.