Addendum to the fashion post: figure out your weaknesses
After reading the comments to fashion and clothes for players, I thought about the two black guys I've known who did well with white chicks. Both of them did the basic stuff right, like lifting, but they also dressed "up" at least one level compared to anyone else in a given situation. If everyone else wore jeans and t-shirts, they'd be in dress pants and a collared shirt. They wore suits much more often than I would recommend for the typical guy.
Why? Since neither was (or is) stupid, they understood that they needed to play against and overcome stereotype. That meant dressing better than the average guy, speaking better than the average guy, and being friendlier/warmer/more smiley than the average white guy. Their (probably subconscious) goal was to communicate to chicks, "I am friendly and am not going to hurt you. I have my life together." Their goal was to avoid the immediate reaction (which, sorry black guys reading this, is often justified in everyday experience).
My goal is usually to NOT appear like a boring office drone. Given my life and personality, I need to increase my implied "edge" and not seem to boring. Both the guys I'm thinking of, needed to convey other ideas to functional, middle-class chicks and higher. Contrary to what you may see in porn or elsewhere in anxious men's writing, most functional chicks are NOT attracted to low-class and ghetto behaviors / personas. The exceptions tend to make for spectacular stories, but they are exceptions.
It's possible that lower-class/ghetto behaviors are effective with equivalent girls, but I don't know a lot about the bottom-level world of true social and economic dysfunction. My sense is that most chicks in it are fat/ugly by their early 20s if not sooner. When I did conventional online dating I would run into occasional girls from that world, and even had sex with a few, but we never really got along correctly because the cultural/intelligence chasm between us was too wide. Plus, as I said, I think most chicks in that culture have terrible diet and exercise habits, so even if they start off as attractive teenagers, the decline is swift. Perhaps other guys can chime in with experiences.
There might also be a world of super rich people hooking up mostly with each other, or where the guys have so much money that the gap between "paying for it directly" and "implicitly paying indirectly" is very small. In this world, maybe it makes sense to wear $5,000 in fancy clothes that other ultra-rich people can recognize. But if this world exists, it's very small and immaterial to me, as well as to virtually all guys who aren't already in it.