To capture a younger market, older businesses have to experiment while maintaining their roots -- just look at Joe Camel, who hooked a juvenile crowd without compromising his venerable lethality. For Old World hats keeping it fresh, check Christy's Crown spring line.
A branch of the Christy's hat company (est. 1773, London), Christy's Crown taps a Miami-based designer to cool-up the line, fusing their centuries-old expertise with tweaked silhouettes, non-traditional deets, materials, and colorways. Woven and lighter fedoras include the "Rocko", w/ a cross-hatch contrast straw weave, kinda-big two-inch brim, and pinch front; the taller and somewhat crushable "Sharla" golf hat, woven into horizontal stripes, with a leather forehead piece; and the eco-friendly, bold-stitched "Swen", made of braided hemp, with a tight, no-nonsense brim that becomes complete nonsense if stuffed in a pipe. Solid cotton and felt fedoras include the Indy Jones-meets-Rocky "Frog", with subtly camo'd cotton, stingy brim, rustic leather band, and padded lining; the wool felt "Mad Hatter", in dark blue or forest green with a feather accent; and one with a yellow & brown plaid top and distressed leather band dubbed "Hedgehog" -- because Spacehog already met their one hit allotment.
Christy's also makes one baseball cap, in a classy tan tweed with a bulldog on the front -- the cartoon mascot who tricked a youthful you into loving Ivy League education.