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During Art Basel, many attendees subscribe to a certain “birds-of-a-feather”

It's a Wednesday afternoon in Miami Beach and I'm feeling underdressed. I'm lunching poolside beneath the palms at the Raleigh Hotel, and looking around at my fellow vacationers, I'm beginning to suspect I've packed entirely wrong for this trip. Ostensibly I've come here to attend Art Basel Miami, one of the world's largest fine art markets, but I'm less interested in the miles of contemporary art on display than the people who've come here from around the world to shop for it.

Like Attenborough crouched behind the bushes at a Tanzanian watering hole, I've followed the migratory flocks of the rich and fabulous to observe their warm-weather plumage as they browse, drink free champagne and dance to the music of Scandinavian DJs. I'd hoped to blend in, at least somewhat, but as I take in the crowd at the Raleigh, I realize that's not going to happen. It's a sweltering 28 C here, the air thick with briny humidity, but despite this (and the fact that the ocean is a block away) no one except me looks like they're headed to the beach.

Dressing for vacation is like dressing for any other event, and requires the careful balancing of weather, occasion and mood. Packing for a week at an all-inclusive, where I'd be surrounded by other sunburnt tourists sipping daiquiris on lounge chairs, would be easy: comfortable clothing, short sleeves, maybe a pair of pants. Choosing a wardrobe for Miami Beach, playground of the yacht-owning, art-buying global elite, is more complicated. In addition to beachwear, I need to be equipped for evenings on the town, parties thrown by high-end Swiss watch companies and, of course, poolside lunches in the palm-shaded courtyards of hip boutique hotels. While Miami might be very close to Varadero in terms of geography, style-wise it's a different planet. Basically, I should have left the shorts at home.

Part of my agenda in Miami was attending the launch of BMW's latest Art Car, a Daytona-ready M6 daubed with colourful dots and the word "FAST" by octogenarian artist John Baldessari. I'd brought a navy blue suit for the occasion, and while I knew enough not to pack a tie, my footwear was all wrong. Men who wear suits in Miami Beach wear them with white sneakers, not black wingtips. Even Baldessari, whose long white hair and full beard stood out among the clean cut BMW executives on stage, capped off his black suit with a pair of Adidas Sambas.

Much like Cannes, St. Barths and other places the rich and sun-loving congregate, one gets the sense that the people at Art Basel Miami Beach spend a lot of time around each other. Like tattooed, bearded hipsters, sneaker-loving streetwear guys or Bay Street bankers, the men here have a certain shorthand to the way they dress that marks them as birds of a feather.

This beacon of quiet, wealthy conservatism is remarkably consistent: a navy blazer worn with white or pastel-coloured chinos, a white shirt and brown or blue loafers worn without socks. At least one item of clothing (but no more than two) should be linen, and a seersucker blazer can be substituted, but not seersucker trousers. Accessorize with interesting eye glasses, a Patek Philippe Nautilus watch, a deep tan and swept-back hair that's slightly longer than is office-acceptable, and you'll be ready to bid on a Mondrian or discuss the prices of real estate in the Seychelles.

I don't know if I was the only one who wasn't aware of this rich-guy-on-vacation dress code, but fortunately I wasn't alone in flaunting it. At Art Basel's preview day, where celebrities and high-flying art buyers peruse the show before the hordes of looky-loos and scenesters arrive, Sean "Diddy" Combs stalked the galleries in a pink varsity jacket, peering at the Basquiats through his sunglasses. Los Angeles real estate mogul and Lakers superfan James Goldstein, meanwhile, wore an outfit of head-to-toe animal skins accented by a leather cowboy hat, despite the sultry Miami heat. Combs is a sometimes fashion designer, Goldstein is a rich weirdo, and both have embellished their celebrity with the help of bold wardrobe choices.

Not everyone who stood out, however, did it for this reason. Nearby a trim older gentleman browsed a selection of Kandinskys in scuffed boat shoes and a Breton-striped polo shirt, his khaki shorts held up by a belt embroidered with maritime signal flags. He was silver haired, barely five feet tall and sported an exceptionally deep tan. Was he shopping for something to hang in the stateroom of his yacht? Perhaps. Did he worry about being the only man in the entire building wearing shorts? I highly doubt it. Among the linen blazers, Italian loafers and pastel trousers, his spindly caramel-coloured legs were a revelation: Anyone can dress like a rich person. Significantly harder is dressing like you genuinely don't care.

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