At the tail end of the 19th century, Praça da República was hardly very republican—instead it was a posh downtown square around which São Paulo’s coffee barons built lavish city dwellings. However, as commerce—and its attendant trappings of noise, traffic, and riffraff—swept the city’s center, the barons decamped to a new and more bucolic neighborhood that came to be known as Higienópolis.

Former downtown mansions were quickly (and lamentably) destroyed, giving way to modernist buildings, some of them still quite lovely, others sadly run-down. Today, Praça da República is a vibrant but somewhat forsaken square in need of a good renovation. On Sundays, it is the site of a colorful crafts and antiques market.

Two of the standout modernist buildings off of Praça da República have become Paulistano icons. Constructed between 1956 and 1965, Edifício Itália (Av. Ipiranga 344, Centro, tel. 11/2189-2929, www.terracoitalia.com.br) was built with the mission of surpassing the reigning Banespa building in height. And indeed, for a long time, it proudly held the title as tallest building, not only in town, but in all of Latin America. Today, it is still top-ranked among the city’s skyscrapers. To take in the glorious view, ride the elevator up to the swank Terraço Itália restaurant, on the 42nd floor. If you don’t want to splurge for a mediocre meal or pay a cover charge at the bar, during the week between 3 and 4 p.m. visits are free.

Quite striking from the outside is the Edifício Copan (Av. Ipiranga 200), a curling S-shaped building that could only have been dreamed up by Oscar Niemeyer. The building is as famous as a living space as it is for its design—boasting over 1,160 apartments and close to 6,000 residents, it is rare the Paulistano who hasn’t known someone who has lived here at some point in time.