Today Adam Kimmel will headline Pitti Uomo in Florence with a preview of his Fall 2008 collection, a rare honor for an American designer. In one sense, it's simply recognition of the rise of a new wave of stateside talent. In another, it can be read as an acknowledgment by Pitti's Italian organizers that things ain't what they used to be. Much has been written lately about a return to elegance in menswear—and there may be something to that—but talk privately to the top executives at the more traditional Italian menswear houses, brands once considered as bulletproof as James Bond's tuxedo, and you hear the same thing: a concern, cautiously worded, about how they're going to attract the next generation of customers.

This is why everyone is watching Tom Ford so closely. Can a business that ostensibly offers a new vision but that is solidly based on the pillars of traditional luxury tailoring succeed? As Ford ramps up his expansion plans over the next year, a clearer picture will emerge. Ford's partner, of course, is Zegna, which as it happens has forsaken Pitti in favor of a presentation in Milan this season. Changes are afoot elsewhere, too. The Valentino men's collection, which has always offered a compelling if vaguely unattainable vision of international swank, has a new designer in the wake of the founder's retirement: Ferruccio Pozzoni, a veteran of both Brioni and the more fashion-forward Prada. It will be interesting to see which direction he'll favor for the line. In the meantime, Kimmel's show will take the form of a banquet, featuring many of his New York artist friends. No one is about to count out the Italian masters, but right now it's clear who's having more fun.