DKNY presented its latest menswear collection at the glass-walled Nasdaq MarketSite building, the first men's brand to do so. Donna Karan listed her company on the New York Stock Exchange back in 1996, which made you wonder: Why this venue now? DKNY's collections, which consist of tweaked classics brought ably up to date by the line's creative director, Garry Martin, include plenty of tailored options—this season, a whole passage of city-block-gray two-button suits—but they're far more casual than you're likely to see on Wall Street bankers. (Here, the suits were shown with platform-heel Doc Martens; other looks had Superga sneakers and still others, Tevas.)

But that's a strength, not a weakness. DKNY's mandate is clothes—working weekday and casual weekend—for the young and the urbane. Martin interpreted that dictum to demand versatility, not only office to evening and back, but all-weather and idiot-proof, too. Blazers and suit pants got nanotech finishes for water- and stain-resistance. Every jacket now has an iPhone pocket hidden in its bonded lining.

Outside, overlooking Times Square, coordinated Jumbotrons blasted DKNY's Fall campaign. With that, the venue clicked. Karan's secondary collection may not be for bankers, but it's always been about going big in New York. Remember the famous city-skyline billboard on Houston Street? The MarketSite's glass panes were the perfect way to take in the view.