(Photo: Brigitte Lacombe. Styling by Kate Young; Hair by Italo Gregorio; Makeup by Fulvia Farolfi for Chanel. On Monroque: vintage Dolce & Gabbana Bodysuit and vintage Alaïa shoes, both at Albright Fashion Library.)

Shala Monroque arrives at a restaurant in Soho for lunch on a steaming summer day, her arms brimming with packages from the Prada store on Broadway. As a street-style icon and fashion demi-celebrity who has the distinction of being a central inspiration for two of this era’s most powerful visual tastemakers, Monroque, 32, is impeccably dressed, of course, in a sleeveless denim shirt paired with a knee-length denim skirt. She’s a friend of Miuccia Prada, for whom she functions as a kind of muse and unofficial ambassador, hosting a salon called Miu Miu Musings at the stores around the world. And she’s the girlfriend of art-world impresario Larry Gagosian, the foremost gallerist on the planet. In her bag are Prada’s crazy Minimal Baroque sunglasses, ­embellished with bawdy scrolled lines like a violin’s carved neck, in the same color as her denim. “I’m in my blue period right now,” she says, with a bit of a wink.

Monroque orders tuna tartare, then gives a nervous laugh. She’s a shy woman, slightly formal and sphinx-like. She abhors talking about her life, unspooling stories reluctantly. Monroque was brought up near the beach in St. Lucia, where her family still lives, and didn’t leave the island ­until after she graduated from high school. “I always knew as a kid that I wanted to live in America,” she says, choosing her words carefully. “We always got all of the American TV shows late, and I grew up watching Leave It to ­Beaver and other shows from the fifties. Life here just seemed better, and freer. I couldn’t believe that on TV, kids would just open the fridge, pull out a box of orange juice, and drink from it.”

Monroque’s mother ran a gift shop at a hotel, and she brought her daughter copies of the Vogue and Tatler magazines that the shop couldn’t sell, usually tearing off the front covers so that they could be sent back to the publishers for reimbursement. She was also close with her aunt, who made trips to New York’s garment district every few months to buy copies of high-fashion American clothes for Trendy’s, a boutique she ran on the island. “I always loved dressing and had the newest things, but I always had the fifties ideas,” says Monroque. “Once, my mom bought me a dress with a tie around the waist, trying to tie it in my front, but I wanted to tie it in the back.”

As a teenager, Monroque was a track star, wrote poetry, and entered beauty contests, coming in second in a St. ­Lucia carnival-queen pageant. The prize was a ticket to ­Miami. “There wasn’t anything to do in Miami, though,” she says. “I had always had this romantic idea about taking a Greyhound bus, so I thought I’d take the 30-hour trip to New York.” She met a guy who tried to sell her a phone that she could use anywhere in the world by satellite (“I didn’t quite understand what he was saying, but this was twelve years ago, so I guess it was a mobile phone and legit”) and another one who told her, when she said she was going to New York, “I can see you’d love it there. You’d fit right in.” She stayed with her uncle in Rosedale, Queens, and was initially unimpressed by the stink and sloppiness of the city—until she visited another aunt, a dresser at fashion shows. “The moment I knew I wanted to live here is when I got to go to a Jean Paul Gaultier party,” she says, smiling, “and there were red knee-high feathers throughout the whole floor.”

Baby-sitting was the most obvious job for a woman from the islands, but her uncle dissuaded her, because “he thought it was ­demeaning for me to look after another woman’s kids.” She started working at a photo studio for $200 a week. Then she figured out that unemployed actors and models (she tried to model herself, but she couldn’t get traction) were making a lot more in restaurants downtown. Monroque began hostessing at Man Ray, and then Nobu, which provided enough liquidity for her to secure a kitchenette with a shared bathroom in Harlem. For clothes, she mostly shopped at Daffy’s on 34th Street (“If you look for the right fabrics, you can find good things”) and made her first purchase of a luxury item: dark wraparound glasses with little gold screws. “Very intense, like something guys from St. Lucia would wear,” she says. “They cost me a fortune, more than I was making in a week.” And her next purchase? Monroque pauses. “I’d say there was a big gap after that.”