Welcome to the Dollhouse (Donna Bascom (Executive Producer), and Todd Solondz (Director). (1995).Suburban Pictures/Sony Pictures Classics.) This movie has very little to do with consumption, and very much to do with conduct. It presents the idea of the outsider who is NOT followed: the rebel who acts in genuine incomprehension of the world of others. (Anti)heroine Dawn Weiner ("Weiner Dog" to her peers) simply cannot make right out of her wrongness. Her outlets for this discomfiture are classic adolescent anti-socialism (she picks on her little sister, for instance), yet she continues to strive for an ingress into the normal, "cool" world.
Rebel without a Cause (David Weisbart (Producer), and Nicholas Ray (Director). (1955). Warner Bros.) "Teenage Terror Torn from Today's Headlines!"
The Subterraneans (Arthur Freed (Producer), and Ranald MacDougall (Director). (1960). MGM.) Based on Jack Kerouac's novel of the same name.
Movies and criticism of John Waters, "the Pope of trash"--Waters being absorbed with the concept of coolness, and the cult of the outsider. Ricki Lake in "Hairspray" is classic: a fat girl with an unlovely family (obese transvestite Divine plays her mother; need I say more?) who through skillful self-promotion gains access to the upper echelons of Baltimore's teen scene. There's also "Pecker," in which Edward Furlong's innocent camera eye is glommed onto by the New York artworld glitterati with nearly destructive consequences for his idiosyncratic (and suddenly cool) community. Waters's point seems ever to be that the original is, of necessity, ultimately inexplicable--non-formulaic, transgressive, and fearless more out of ignorance than actual bravery.
All of Edith Wharton's novels except "Ethan Frome", but most particularly "The House of Mirth" and "The Custom of the Country."
The Baffler, which is published irregularly but with great gusto. It's self-described as "the journal that blunts the cutting edge" and offers some truly great left-ish cultural criticism (articles like "Why Johnny Can't Dissent" and "Trouble in the House of Cliche"), when it's not completely full of itself. Find it at an independent bookstore near you. The Baffler also has its own list of books, which you may order by mail.
Fat glossy magazines with more ads than editorial content and an upscale readership, because you might as well keep up your socio-visual vocabulary.