Social distinctions based upon money are more or less common knowledge and par for the course. My high school is no different. Just like in adult social circles, people know 'who's who' and who's got the real money. As teens, though, location is not yet as important as it is to our parents. Sure, the idea of Hunting Valley as the playground for the wealthy exists in a very real way, but it doesn't play a huge role. I think that the size and feel of your house and property makes more of a difference than where it's located.
While the fact that I live in Chesterland isn't necessarily a social handicap, it did mean that I had some catching up to do after I switched from public to private schools in middle school. Social norms were definitely something that I had to learn very quickly, but it wasn't until seventh and eighth grade that I really picked up on the material differences, and by freshman year, they were blatantly obvious.
As far as clothes are concerned, I'd say that there are three 'tiers' of clothing. First, you've got boring or unfashionable clothes of unknown provenance. These are to be avoided at all costs, unless they are unobtrusive and inoffensive or paired with more acceptable attire. Second, you've got the ubiquitous but standard mall-rat brands: American Eagle, Hollister, Abercrombie & Fitch, H&M. Accepted, recommended, absolutely allowed. Third, you've got the saliva-inducing expensive level. This includes Juicy Couture and designer denim such as Seven for All Mankind, Joe's Jeans, True Religion and Rock & Republic. However, only the well-trained eye can identify the little 'J' shaped zippers on Juicy sweaters or the horseshoe embroidery on the back pockets of True Religions.
Once you're sporting a great outfit and flawless skin, you look the part. But can you walk the walk? Just flashing your new BMW keys around won't cut it. Indiscreetly flaunting one's (parents') money is a scornful activity for tactless social climbers. Old money families are so used to expensive clothing, accessories, cars, exotic vacations and palatial estates that these playthings are ordinary. The key to old money elite behavior seems to be lavish normalcy.
'Fitting in,' as the school psychologist would characterize social survival, is more a function of your adaptability than your parents' stock portfolio, because YOU are what your peers have to put up with every day. There are, however, a few mysterious guidelines. Attractive people are usually well liked, and the right physique will take you almost anywhere (curvy-but-slim girls (think Beyonce or Shakira) and ripped guys). I say 'almost' because there is an additional, essential component: Your vibe must seem natural. No one wants to be friends with a fake.
As far as the educational institutions that mold these future Louis Vuitton-toting, BMW driving-kids are concerned there is a great divide between private schools. The snob quotient increases as the schools become more traditional. The 'mean girls' stereotype seems to be much more prevalent at all-girls schools. At one, for example, each exclusive social clique has a different hair ribbon to signify membership.
I, myself, don't feel much pressure to fit in. I feel like I've short-circuited the system: I'm not seeking approval, so I'm not really subject to the uncomfortable exclusion that pressures many kids to conform in the first place. Why would I put effort into cultivating an image tailored to a group of girls whose measure of personal worth is, say, wearing green hair ribbons?
In short, the efficacy of buying coolness is spotty at best. Although there are a few anomalies, you can't purchase popularity. Electric personalities are the most valuable currency in the high-school market. The only way to be a cool kid is to posses the intangible effortless 'awesome.' There are plenty of weirdos in very expensive shoes.