"Now I like to buy more expensive higher quality stuff (not like offwhite and these other designer cloths), and I do want to look good."

Not sure if you're in the category of gifted&talented but the more that someone is able to think in the long-term the more they realize that low quality clothes (or low quality anything) is actually paradoxically the more expensive option.

So let's take shoes as an example. I own $300 hiking boots, but it's possible to buy okay-quality hiking boots for $100. The difference is that the $300 option is of a much higher quality, so they fit better, they're more comfortable, they're waterproof, they last longer.

With high-quality clothing it's the same thing—they last longer, they survive the washing machine, they fit better, they're more comfortable, etc. High quality clothing, high quality shoes are a form of investment, not cost. So long as increased cost is represented by increased quality, or rather increased investment value, the cost is reasonable. When investors construct a $50 million building, they're not concerned about the $50 million, their concerned about their return on investment.

Thinking in terms of investment value, rather than cost, is a very healthy habit to get into.