So many times I heard something like this: "I have no sense of style..if it had been, I could become cool fashion designer/illustrator/make-up artist..". It is fair to everyone else "if".
if I had enough free time
if I had enough money
if I had talant and luck
forget about it.
It is absolutely possible to develop sense of style and to be honest, it's possible to achieve almost everything you want, except travel in outer space may be.
I do not want to sound like hundreds of books on motivation, but believe in yourself is very important in such a competitive industry like fashion.
So when it comes to learning, you should not doubt. Sense of style can be just learned.
As I seen before in other media, there are many advices like "read a lot of glossy magazines, try to copy their style and later on you will be able to create good looks by yourself". I'm totally disagree. It looks like a simple way, but it won't give you the full picture.
So, this is my advices how to develop sense of style:
1. Expand your horizons. It is best to start with books: classics and books on art.In addition to general education, it gives you some sense of beauty. Now, this feeling is largely distorted and suppressed by the modern culture, so that an understanding of the sources is essential.http://www.bbc.co.uk/arts/bigread/top100.shtml - nice list by BBC, including authors like Jane Austen, JD Salinger, Lewis Carroll and many others.
2. Pay attention to painting and art. It can be great source of inspiration and also you will get used to harmonious combination of colors and the laws of perspective.
3. Analyze works of the great designers. History of fashion is a very eloquent. And try to note the difference in the works of masters and understand their own style.
4. And only here it's time to read and draw some conclusions from magazines.
If you really would follow these easy advices and go deeper into classic books (including modern literature, but worthwhile), learn history and evolution of art - while looking on pictures in magazines you won't see "cool clothes", but finished composition of lines, shapes, colors and fashion.
Good luck and waiting for you comments to discuss.