Fashion: Who wore it better, Kelly Slater or “tragicomic” Harvey Weinstein? 

Harvey Weinstein's suit fights a losing battle against gravity and excess to Kelly's bulging athleticism.

Can you believe it’s been a dozen years since WSL owner Dirk Ziff celebrated pro surfing’s just-opened New York office with summer cocktails at the James in Soho alongside Kelly Slater, Steph Gilmore, Gabriel Medina, super producer Harvey Weinstein – who knew!, Katie Holmes, Anna Wintour and Matt Lauer. 

It was a fabulous event, by all accounts, and will long be remembered as the zenith of the WSL. 

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As the company’s then-CEO Paul Speaker said, “Planting a flag in the media and marketing capital of the world, New York City, is a natural extension of this growth and places professional surfing in line with all major sporting leagues in terms of proximity to major partnership opportunities.”

It didn’t work out that way, of course, and though it will go down as a curio of history, Weinstein is currently at Rikers Island waiting a retrial for sexual assault charges, the almost identical outfits of Kelly Slater and Harvey Weinstein do bear commenting. 

Twinned in sartorial communion, a matching set of suits, one grey, one black, layered over plain black crew-neck tees.

No ties, no pocket squares, no fuss, just the barest suggestion of formality stripped down to its muscular, minimalist bones.

The look, if you’ll rememeber, is that late-aughts/early-teens casualisation, the great democratic unraveling of menswear where the suit began flirting with the street.

Think back: by the mid-2000s, the black t-shirt under a suit had already become the uniform of the moneyed creative class. Steve Jobs had canonised the black mock-turtleneck years earlier, but the broader brigade, the directors, tech barons, musicians, had popularised the plain black tee as the ultimate anti-shirt.

Grey suits (mid-weight wool or wool-blend, single-breasted, notch lapels) paired with it offered just enough polish to pass muster at a cocktail party while signalling you were too cool, too busy conquering worlds, to bother with a proper dress shirt and tie.

The combo peaked in that hazy 2010–2015 window: red carpets softened, Silicon Valley invaded fashion weeks, and suddenly every man who mattered wanted to look like he’d just stepped off a private jet and into a gallery opening.

Who wore it better? Kelly Slater or Harvey Weinstein?

The contrast is tragicomic. The same outfit, yes, but on a frame built for boardrooms and backlots rather than reef breaks. The suit strains slightly at the buttons, the fabric pulling where Kelly’s drapes; the black tee sits heavier, less like armour and more like a shroud over ambition’s bulk.

It reads as camouflage, power disguised as nonchalance, but the effect is oh so laboured, the tailoring fighting a losing battle against gravity and excess.

I was reminded, along with everyone else, of the event thanks to the excellent Sterling Spencer podcast where Joel Tudor said many inflammatory, and very untrue things, such as, 

“The guy that owns the WSL was Harvey Weinstein’s main man…you want some shit dude, go get that shovel out… that should tell you why the WSL is as tacky and dorky as it is.”

What a time to be alive, yes?