From my surroundings (a little hick town in the Maritimes of Canada), one can find it specially difficult getting on bored of the whole 'fashion thing'. I was by nooo means born with in a family who gave damn about fashion or clothing. More or so of hockey, and food.
One thing however I found interesting is how you appreciate clothing. People complain about not having this and that designer boutiques in their area or close by city, or simply some retail branches of Barney's, Zara and the like. You work with what you have, the resources and your money budget. I find my self putting in a effort to be absolutely 100% sure x-store is selling what I want, the quality I want and being completely positive I'll actually wear what I'm buying. Because of this, you just well, appreciate the experience of shopping, you don't find your self following trends as much because how long will you be wearing it?
I only go the States twice a year, and buying online is a hard job at hand. I have to make sure my parents approve the item(s) I'm buying and give them all the details of shipping and whatnot. Heh, I remember my dad automatically disapproving from buying of AA because of it's sultry advertising. It took some time to get him to say yes, but it happened.
It's almost like quality-control in my wardrobe. I don't like throwing an clothing item away from Zara, etc (or any place for that matter), only because I feel rotten waisting that one time experience and money on a shirt I never really worn.
Anyhow, I don't specifiably think you have to be some sort of hick to really admire the workmanship of clothing, you could be from freaking NYC or some fashion conscious area and have the same level admiration of myself or anyone. I'm just happy at least there is one thing from being in a ridiculously small town can help me love style just that much more. As cliched that may be
As for this effortless style and born with style ... I think it comes down to knowing what looks good on you, how you love your clothing and feeling comfortable/confident, that automatically comes to show. I don't think it's the actual style its self this person is wearing, it's how they present them self's with the clothes they are wearing.
Sometimes I feel people "hate" peoples choices on clothing because it's simply something they don't feel themselves is too this and that (not their personal style basically) ... as long as they look tastefully done, I don't see the problem. Though ... people have different views on what is tasteful...