In celebrating Ocean Drive’s 20th anniversary, it’s become clear to us that fashion has produced some of our favorite and even most heartbreaking moments. These events surprised us, marked the rebirth of neighborhoods, brought our town and its talent to the attention of the world, and in turn brought the talent of the world to us. Fashion, as we see it, is a vital, fun, and sometimes poignant part of the Miami tale.

1. Taken Far Too Soon. In a still bohemian South Beach, Gianni Versace cut a figure of supreme elegance as he traveled a daily route from his waterfront villa to the News Cafe, where he went for breakfast and read the papers each morning. The parties at his grand home attracted a glamorous crowd, until the morning of July 15, 1997, when Andrew Cunanan brazenly shot him on the steps of his home and set off a manhunt that had the world glued to its televisions.

2. Igniting July. Mid-summer was traditionally a sleepy time in Miami—until SwimShow kicked it into high gear in July 2005 with a double-barreled, five-day trade-show extravaganza that has grown so big it’s held at the city’s convention center and includes runway shows from international designers at a bevy of the Beach’s top hotels.

3. A Local Protégé Emerges. Though it was a small capsule collection at the Shore Club, Esteban Cortazar’s 2002 show at the hotel launched the career of the 17-year-old designer. Ten of his dresses were displayed in rose-petal-strewn Plexiglas boxes in the hotel’s garden, while novelist Tama Janowitz and designer Brian Atwood looked on. Nina Garcia, then fashion director of Elle, flew in from New York, and Bloomingdale’s Fashion Director Kal Ruttenstein’s attention was captured. “Kal referred to Esteban as ‘a young Yves St. Laurent,’” recalls Tara Solomon, who represented Cortazar.

4. Fashion Takes Up a Cause. Launched in 2004, Destination Fashion, which helps fight paralysis, was so big it closed down the Bal Harbour Shops. This year will mark the event’s last, but the one people remember best is 2009, when Michael Kors showed his collection. “It was full of neon oranges, bright pinks, and vibrant yellows—so Miami!” recalls the event’s creator, Stephanie Sayfie Aagaard. Of course, it didn’t hurt that Gloria Estefan, Jack Nicklaus, Tommy Lee Jones, and Julio Iglesias were among the crowd.

5. Luxury Finds the Beach. Miami had small boutiques and department stores, but when The Webster opened in 2009, it turned the city’s fashion scene on its ear by introducing a chic, high-end Parisian emporium à la Colette. The trilevel store carries a wealth of labels, including Balenciaga and Stella McCartney, along with several young emerging designers.

6. A Stamp of Approval. Herb Ritts’s knack for bringing out the most beautiful aspects in his subjects scored him some of the most important fashion campaigns and best videos of the ’90s. So when he put his imprimatur on Miami in 1995, choosing it as a location for his Valentino campaign (with Michele Pommier girl Christy Turlington as the model), other photographers and producers followed his lead.

7. The Skin Game. In 1992, the streets and beaches of Miami were the backdrop for much of Madonna’s controversial coffee-table book, Sex, which explored her fantasies, from bisexuality to bondage to bestiality. Shot by Steven Meisel, the images of the Queen of Pop emerging nude from the ocean or climbing a wall in heels, thigh-high tights, and an exposed butt did wonders for tourism, and no doubt contributed to Sex becoming the bestselling coffee-table book in history.

8. A Visit From an Icon. Anna Wintour sitting poolside; Diane Kruger, Zoë Kravitz, and Anna Kournikova looking on; and leggy models in black and white prancing along the curves of The Raleigh’s spectacular pool—these are all indelible images from Karl Lagerfeld’s Chanel Cruise collection show in 2008. And to top it off, the US Olympic synchronized swimming team falling sideways into the water—like a scene out of a Busby Berkeley film—made tented venues seem forever dull.

9. Quenching Miami’s Thirst. What began in 2002 as a one-day Ocean Drive Fall Fashion Celebration event at the Sagamore Hotel evolved, by the following year, into a four-day extravaganza, with multiple shows, luncheons, and cocktail parties. Unlike other fall fashion shows that previewed spring styles, these designs were in the stores and available at the moment.

10. A Ball of a Time. Calvin Klein, the master of American fashion, may have allowed only white flowers in his austere New York showroom, but in Miami he cut loose at Ocean Drive’s Volleypalooza in February 2004. Relaxed and shirtless, he cheered on models from 18 different agencies as they competed in a rousing volleyball competition on the beach.

11. Growing Room. What could be more emblematic of breaking out from a cookie-cutter mall environment to more open spaces than a bold graffiti mural by Retna? Louis Vuitton chose the street artist to emblazon the front of its temporary Design District storefront in 2012, which marked the beginning of LVMH brands migrating to the neighborhood.

12. Tapping Talent. When Tony Goldman and his daughter Jessica Goldman Srebnick selected Todd Oldham to design The Hotel in 1998, it was the first time an American fashion designer was chosen to create hotel interiors. Oldham’s vision preserved historical elements of the 1939 building while imbuing it with vibrant colors and artisan detailing. The project received dozens of awards. As Susan Brustman, the hotel’s longtime rep, recalls, “Oldham’s design for its garden restaurant, Wish—with its gleaming mosaic fountain, bright colors, and tropical foliage—was pure magic.”

13. A Benchmark Event. If you weren’t there, then you heard about it: This lofty event in 2011 for Van Cleef & Arpels paid homage to an enchanted forest by creating a mirror ball in a hangar at the private Opa-locka Airport. The black-tie evening featured live performance art conceptualized by Nick Cave and Vanessa Beecroft, along with a dinner by Daniel Boulud.

14. Ahead of Her Time. When Gretchen Mol and a crew took to our beaches to shoot The Notorious Bettie Page in 2005, it caused such a resurgence of interest in Bunny Yeager’s shots of Page and other 1950s pin-up girls that the octogenarian’s career was revived. Rizzoli wound up publishing Bunny Yeager’s Darkroom last year—a collection of iconic shots, including the playful Florida portraits of Page with cheetahs.

15. A Global Audience. In a brilliant public relations move, the Fontainebleau Miami Beach hotel held a Victoria’s Secret Fashion Show in 2008 to unveil its multimillion-dollar renovation. Mariah Carey performed, Angels walked in jewels, and the property shone. Gwyneth Paltrow, Diddy, and A-Rod were among the spectators. “The hotel opening was down to the wire; there were still hard hats around the property,” recalls Desiree Gruber, whose company does marketing for Victoria’s Secret.

16. A Colony of the Beautiful. With the local expansion of modeling agencies by Irene Marie (who discovered Niki Taylor) and Michele Pommier (who found Christy Turlington) in the ’80s and ’90s, genetically blessed gazelles not only posed all over town but helped fuel the nightlife fire. “I sent a representative to Germany to solicit clients; then the Europeans started coming to South Beach, and everyone else followed,” remembers Pommier. “There were 15 Winnebagos lined up shooting on Ocean Drive every day.” As a result, Miami appeared in fashion magazines and catalogs all over the world.

17. Rocked by Fashion. In 1998, MTV married rock and hip-hop with runway fashion at Fashionably Loud. Models wearing Jean-Paul Gaultier and other designer labels strode the runway at this oh-so-hot event to live performances by Jay-Z and Kid Rock. “I was 14, and all of a sudden the people I was seeing in Italian Vogue were on the beach,” remembers designer Esteban Cortazar. “Even English designers were there, including Alexander McQueen, who wasn’t even showing, and it brought a younger fashion clique to the area.”

18. Southern Salvation. Before 2002, shoppers in South Miami looking for a hub of luxury fashion had to travel all the way up to Bal Harbour. To launch the opening of the opulent Village of Merrick Park in the middle of Coral Gables, anchor stores Neiman Marcus and Nordstrom each threw massive parties with fashion shows, and wowed guests with designer boutiques within the department stores.

19. A Lot of Fashion. The idea of putting on a fashion show in a parking lot may seem bizarre now, but it was a bold move back in 1998 when Tommy Hilfiger brought his pop- and hip-hop-inspired styles to a makeshift runway at Dadeland Mall. He shared the stage with Rebecca Romijn and rapper Mase, and made himself accessible, signing autographs and greeting the enthusiastic crowd. Smart move—Miami was his biggest market.

20. Pioneers. When the Design District was little more than an afterthought below I-195, luxury retailers Marni and Christian Louboutin took the plunge, following developer Craig Robins’s lead in 2009 as he set out to turn the neighborhood into the city’s version of Rodeo Drive. It turned out to be a prescient move—Prada, Louis Vuitton, and Hermès followed.

Like what you're reading? Get it delivered straight to your inbox. Sign up now for our newsletters >>