Dressing "naturally" is seriously difficult business, but it shouldn't be stressful. Anyone can pile on a ton of in-your-face clothing and stand out from the crowd. But what's really impressive is the guy who looks comfortable in his clothes and like he dresses effortlessly. If you don't enjoy dressing, everyone can tell. I promise.
Think about the stuff we typically call "basic": grey suit, navy blazer, dark brown shoes, etc. Nothing flashy, nothing complicated. At least at first glance. You quickly come to realize though, that a seemingly obvious descriptor like "dark brown" means literally hundreds of nuanced possibilities. And if you ask five other guys, you'll get at least ten opinions on which dark brown is "right." It takes time to learn these things, and for the sartorially-minded man the journey is never really over. If you think you're going to master it over night, you're missing the point already. And most importantly, there's no rush.
When just starting out, you'll hear you need a navy tie. "If you only have one tie in your wardrobe, it should be a plain navy tie," or some such nonsensical aphorism will be thrown your way. So you go out and buy a decent-quality navy tie. It's not bad, and you like it just fine for a while. But over time, you'll start to realize that "navy tie" is just as vague as "grey suit." Should I have bought a grenadine instead of a plain twill? Is the width exactly right? Is it too shiny for day wear or too matte for the evening? You can always find more details to obsess over.
They key is not to stress out over it. 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.