Something occurred to me the other day, and although it's not a really big idea, I thought it was significant enough to merit its own post:
The only way to learn how to dress well is to expose yourself to people who know how to dress well.
It occurred to me via the parallel example of writing. I have a friend who's doing his Ph.D. who works as a TA, grading first-year papers. Whenever we talk about it, he's always flabbergasted by the number of students who have managed to reach the university level who are actually terrible writers. Improper sentence structure and punctuation, words used in incorrect contexts... we always ask ourselves how these students could get so far with such a seemingly tenuous grasp of the English language.
Now, I'm a philosophy major who went to law school; my wife is an English and media studies double major who also has a master's in library science. Both of us grew up as voracious readers. My mom would look through the Chinaberry catalogue every summer, compiling a list of books I should get out from the library and read over my vacation. The thing is, I liked reading. I used to read at recess, even though I got teased about it; I used to read in the car, even though it made me carsick. My wife would read in the stands at her younger brother's hockey games.
But here's the point: all that reading showed us what good writing looked like. It showed us how a sentence was supposed to sound; it showed us new words used in their proper context; it showed us how to use semicolons and dashes. So in our own writing, we'd be able to look at something we'd written and think, "Hmm... that doesn't sound right." People who have never been exposed to the correct way of doing things have no way to tell when they're doing something wrong. It's the same with learning a language, and it's the same with style, too.
I never had any style role models when I was growing up. The way my parents taught me to dress was, I regret to say, unfashionable. It wasn't until late in my undergraduate years of university that I really began to be conscious that there was a correct way to do clothes, and began to read magazines and websites and books about clothes. By looking to others who knew what they were doing, I slowly learned how to put clothes together, how they should fit, and just fundamentally what looked right and what didn't.
So, if you're wondering how you can get started, pick up a copy of GQ once in a while (I prefer it to Esquire). Look at celebrities like Brad Pitt and George Clooney and Daniel Craig, even Stephen Colbert and Jon Stewart. When you watch movies and TV shows, pay closer attention to what the characters are wearing. The more you see, the more you learn, and the better your judgment becomes to choose clothes that work for you.