Even when everything goes exactly to plan, the Oscars tend to find a way to surprise us. This year’s 98th annual Academy Awards were no exception; while the telecast was safe, bordering on boring, and the big awards were more or less dished out to the expected victors (minus a potential Timmy snub, depending on how you feel about ballet), there were still revelations to be experienced: a history-making win for the cinematographer of Sinners, a shock tie and a “Best Dressed” win for Paul Anthony Kelly.
Kelly’s win might not be so surprising — he is, after all, the man who was hand-selected to portray the alarmingly handsome JFK Jr. — if not for the fact that he wasn’t even at the Oscars. Unlike his fellow well-dressed celebs, Kelly materialized well after the last award was handed out, making a (literal) fashionably late appearance at the annual Vanity Fair Oscars after-party.

Regardless of his technical eligibility, Kelly’s A-lister look was undeniable. The actor popped up on VF‘s cream carpet decked out in a sumptuous, velvet brown Brunello Cucinelli one-and-a-half breasted dinner jacket and matching silk-wool trousers. Impossibly louche and fitted to be relaxed but not oversized, the jacket — a custom job, put together by legendary stylist Warren Alfie Baker — instantly evoked images of old Hollywood, especially when paired with Kelly’s Ivy League eyewear, a classic bowtie and some very Cary Grant-coded grooming.
Accompanying the perfectly draped dinner jacket was an even bigger flex — a very Americana, $45,000 Vacheron Constantin. Part of Vacheron’s Historiques collection, a handful of coveted reissues from the brand’s century-spanning archive, the Historiques American 1921 is a sophisticated vision of American excellence, with an idiosyncratic, diagonally offset face, railway dial-train, square design and original detailing — for instance, small seconds between 3 and 4 o’clock — directly inspired by the Roaring Twenties. It’s the perfect watch for a blue-blooded socialite…or a rising star with something to prove.

If there’s one thing that Kelly has proven in his brief time in the limelight, it’s that he’s willing to dress the part; it’s a talent that’s been flexed ad nauseam for his recent portrayal of the mythical style icon. Kelly has donned all manner of nostalgic ’90s menswear in what’s being touted as one of the most stylish shows of the year, if not the decade. (Costuming thus far has included backwards Kangol hats, three-button waistcoats and one of the most coveted watch collections known to man.)
It’s impossible to say what the future holds for Kelly, but, based solely on the strength of yesterday’s red carpet performance, it’s safe to say it’ll probably involve some major awards. Some major menswear, too.
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