When trying to figure out the oldest/deepest questions about our existence on this planet and/or in the universe, the study of nature is the way to go, in my opinion. Even if the answers you seek are not so deep, like style-related stuff, we get some good clues from the ol' mother. Some species of birds put on the most striking displays in order to attract a mate. The more attractive one is, the higher the chance of procreation. Humans, some might argue are a bit more evolved then birds, but the adage of the better you look, the better your chance of getting laid, still applies. Now, let’s look at some choices people make when dressing themselves: there is the all black camp, the norm/classic bunch, the rockers, the ravers, the punks, the drunks, ohh wait I'm not writing a song ...anyway all those camps are wearing uniforms, meaning " i don't want to stand out from the crowd" attitude, and that's fine if you don't have a personality, or are afraid to display it out in public, but you will go to your grave without adding some pizzazz to posterity.
I know it sounds harsh, but hey, I' m not here to stroke egos, I'm here to wake up your inner glam god/goddess.
Now that we covered why we dress, (to get laid) let’s talk about the nitty-gritty of it all.
STYLE, ladies and gents, and everyone else, is synonymous with TASTE, there I said it...We’ve all seen that person who throws everything on but the kitchen sink, and yes, they are being adventurous and even brave, and yeas it's a style, but its Style in BAD TASTE.
GOOD style is about restraint, wit, "an eye"...sort of like what makes a person interesting, I think they call it a personality.
Yes in order to be a good dresser you have to be an interesting person, meaning you have to have opinions about stuff, and be ready to converse with conviction and wit as to why you have those opinions. Once you develop into an interesting person, (which can take a life time) the rest is pretty easy, your clothes choices will come almost naturally, because it will be an extension of you.
The next step is to gain courage in expressing yourself. For me the turning point was, realizing that the people throughout history that we remember for being "cool", are the ones that took risks, not followers of trends, they were the trend setters.
And make friends with a good tailor.