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NEW YORK, NEW YORK – AUGUST 31: Roger Federer arrives on the Blue Carpet on Day Two of the 2026 US Open at USTA Billie Jean King National Tennis Center on Monday, August 31, 2026 in Flushing, NY. (Photo by Michael Mooney/USTA via Getty Images) USTA via Getty Images If can be said to be a “Chairman of the Board” in tennis, it’s the five-time U.S. Open champion and Swiss sneaker-magnate Roger Federer, pictured above replete in a boardroom-ready dark suit. None of this “just-choppered-in-from-the-Hamptons” beachwear/casual-Friday game that some New York notables play at for the ON brand co-founder and investor. Federer Rule No. 1: You don’t dress “like” a tennis player when not on court. Especially not at a Slam. Period. NEW YORK, NEW YORK – AUGUST 30: Tate McRae arrives to the Blue Carpet on Day One of the 2026 US Open at USTA Billie Jean King National Tennis Center on Sunday, August 30, 2026 in Flushing, NY. (Photo by Shea Kastriner/USTA via Getty Images) USTA via Getty Images Canadian singer/songwriter and dancer Tate McRae, pictured above, feels differently about that whole boardroom question. Did we ever know a dancer who didn’t like to give plenty of leg? No. While, yes, the tailored Daisy Dukes, which are plenty short, are definitely in all-business black, the Adidas top screams “beach-wrap” for when that breeze kicks up out in Montauk at cocktail hour, and the queen-bee eyeshades are giving good helicopter. By the way, a chopper charter in from East Hampton into the city will run you $4100 one-way, plus airport fees. Your only worry after the match is how you get back to the beach house. By definition, traffic on the Long Island Expressway is insane anywhere close to Labor Day. Ring up that chopper, baby! NEW YORK, NY…
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