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FROM LEFT: Diners at Santo Grão; Romero Britto’s gallery; Bacio di Latte and its sweet treats

Although it’s tipped as the second-fanciest street in the Americas (behind New York’s Fifth Avenue) and often billed as Brazil’s Rodeo Drive, Rua Oscar Freire is much more than a sleek sidewalk testament to the country’s monetary might.

If You Go...

São Store
Rua Oscar Freire, 841
011-55-11-3086-2278 www.saopaulomania.com.br

Rua Oscar Freire, 1129
011-55-11-3062-6784 www.richards.com.br

Mercadinho Chic
Rua Oscar Freire, 720
011-55-11-3088-2348 www.mercadinhochic.com.br

Agua de Coco
Rua Oscar Freire, 1181

Rua Oscar Freire, 645

Rua Oscar Freire, 1116

Britto Central
Rua Oscar Freire, 562

Santo Grão
Rua Oscar Freire, 413

Bacio di Latte
Rua Oscar Freire, 136
Located in the trendy and lush neighborhood of Jardins in the Southern Hemisphere’s largest city, the 11-block stretch of Oscar Freire (between Avenida Rebouças and Avenida Nove de Julho) is a tree-lined island of calm in a sea some 11 million workaholics strong. Paulistanos — as the busybody residents of the city are known — flock here to forget about the crowds, snarling traffic and frenetic pace of an otherwise unmanageable megalopolis.

Clothing and Accessories Paulistano hearts are torn between three first-division soccer teams: Corinthians, Palmeiras and São Paulo. Oscar Freire is home to one of the official São Paulo FC shops, where you can find baby bottles, baseball caps and bikinis in the traditional red, white and black. Think of massively popular Brazilian brand Richards as a sort of tropical Banana Republic. It’s a must for colorful casual wear that morphs seamlessly from the beach to the bars to the boardroom. For more down-to-earth jewelry, handbags, artisanal decorative items and all sorts of edgy accessories, duck into Mercadinho Chic, a booth-lined upscale market where you can buy unique items direct from the often-revolving designers at off–Oscar Freire prices.

Beachwear It’s 90 minutes or so to the nearest stretch of shimmering sea, but that doesn’t stop Paulistanos from outfitting themselves beach-ready in case a sun-kissed moment calls. The ladies call on luxury-swimwear designer Liana Thomaz and her fashionable brand, Agua de Coco, to ensure comfort over what is often a lack of coverage. Rio export Osklen is a better option for high-end surfer board shorts for men, as well as coastal-influenced T-shirts and shoes, often fashioned from sustainable fabrics. Brazilians reminisce about a time when Havaianas were nothing but a lowbrow pair of $2 flip-flops sold at corner convenience stores. The global must-have sandal brand’s architecturally dazzling flagship store here is eye-catching evidence that those days have gone out with the tide.

Art and Galleries Love or hate his colorful neo-pop designs, Romero Britto is one of South America’s most famous living painters. He has two main galleries in the world — one in Miami and the other on Oscar Freire. Come here for his latest and greatest, flooded with more colors than a samba-school dress rehearsal.

Dining No day spent strolling Oscar Freire is complete without a stop at the city’s best café, the European-slanted Santo Grão, where the cappuccinos are every bit as good as in Italy and the eye candy leaves no doubt as to Brazil’s most striking asset: beautiful people. Excellent breakfasts and bistro fare complement the caffeine and the people-watching throughout the day. Too hot for coffee? Then make a beeline for Bacio di Latte, where a Scot and three Italians have managed to capitalize on a very perplexing São Paulo fact: Despite having a more agreeable climate, a better selection of exotic fruits and a larger population of Italians than Buenos Aires, the city has lagged woefully behind in the gelato department. This sophisticated shop, with cute antique milk cans as barstools, is a game-changer.