From the Beat poets to his father's own Midwestern style, Tim Hamilton's inspirations have blue-collar bona fides not often found in the high-end boutiques where his clothes now hang. More a tension than a contradiction—what's more American than striving?—the juxtaposition entirely suits his background: an Iowa-born designer who's done stints at both Ralph Lauren and J.Crew. Yet it's the way he transcends these influences—rugged Americana, Ivy League prep—that's earned him accolades: The designer was nominated for the CFDA's 2007 Swarovski Award for up-and-coming talent.

For Fall, Hamilton updates his preppy leanings with a muted color palette and rugged materials. His intricately woven knits, for instance, are handcrafted in Italy yet cut in a modern, almost rumpled style. There's also a Japanese silk jersey shirt with a dash of prep from the crest on its breast—what a coal-mining Harry Potter might wear on the weekends. Elsewhere, a hoodie is given the waxed-cotton treatment usually reserved for bomber jackets, while a sweater includes a snap-off collar, which means it can be worn as either a turtleneck or a crew. Hamilton dresses down a wool blazer with a carefully concealed zipper, and moves equally adeptly in the other direction, taking a lumberjack coat upscale by giving it a blazerlike feel and smart button-down hip pockets. It's the most overt Kerouac reference in the collection, and it emphasizes the Hamilton silhouette: skinny but not too skinny pants paired with an artfully rumpled look up top.