I feel your pain man, but it's all about the journey, and it'll take some time.
I'm in the camp that believes that you can buy every piece of clothing you want from Banana Republic or J. Crew and look damn good. In fact, to 95% of the population, you can be deemed a stylish and fashionable fellow. However, those in the know, like those on this forum, are aware of the benefits of owning more high quality garments from higher end brands. Thanks to the knowledge I've gained over the years, I've replaced most of my disposable GAP clothing with higher quality pieces from places like Thom Browne, RLBL, Alden, Gitman, etc.
With research and patience, you'll also learn all about the brands that carry these garments, and will likely start to make a slow transition to paying $250 for a pair of shoes as opposed to $100. It won't break the bank as long as you do it slowly and patiently, and find things on sales whenever they happen (and trust me they always do).
Frankly, a lot of people here probably spend much more than the average person on clothing (in terms of % of income). Nothing wrong with that, but it's a large part of their lives, and a hobby of sorts. Rather than spilling $2k on snowboarding gear, I personally would rather spend that $2k getting a nice sports coat and pair of shoes, seeing as how this is one of my hobbies indeed.
I think you should just try to understand the rules of style, and figure out what types of looks make you happy and confident. Start purchasing slightly more high quality clothing, and slowly work up to the Crockett & Jones shoes if you deem it as a worthwhile purchase. It may not be for you now, but as you enter this world, you'll find that it is.
Anyhow, sorry to bore you with so much talk, but that's just my 2c.
As for brands I would recommend at non-outrageous price points: Brooks Brothers, Hickey Freeman, POLO Ralph Lauren, Paul Stuart, Canali, Barbour, Filson, and Gant Rugger.