Madison Avenue – the avenue of advertising became New York's street of luxury

Madison Avenue has given its name to an entire industry, but on the Upper East Side it is, above all, New York's most refined shopping street. A stroll from Ralph Lauren's castle on 72nd Street to Bemelmans Bar and Sotheby's new house in the Breuer building.

Madison Avenue runs for about 9.7 kilometres through Manhattan, from Madison Square at 23rd Street to Harlem River Drive at 142nd Street. Since the 1920s, the name has been a symbol of the American advertising industry – it is the world depicted in the TV series Mad Men. But on the Upper East Side, between 60th and 80th Streets, Madison Avenue is something else entirely: New York's most refined shopping street, lined with fashion houses, galleries and some of the city's most beautiful buildings.

An avenue that did not exist in the 1811 plan

Madison Avenue was not included in the 1811 grid plan for Manhattan. It was laid out in 1836 between Park Avenue, then Fourth Avenue, and Fifth Avenue, largely on the initiative of the property developer Samuel B. Ruggles. The name comes from Madison Square, which in turn is named after the fourth President of the United States, James Madison.

The advertising agencies largely moved out during the late 20th century, although some remain, according to Wikipedia. Further south, several of the city's landmarks are located on the avenue, among them St. Patrick's Cathedral, Villard Houses and Morgan Library & Museum.

Ralph Lauren at the Rhinelander Mansion

In the southeast corner of 72nd Street, at 867 Madison Avenue, stands the Gertrude Rhinelander Waldo House – a French Renaissance Revival building with a limestone façade modelled on the châteaux of the Loire Valley. It was built between 1894 and 1898 to designs by Kimball & Thompson. Gertrude Rhinelander Waldo had it built but never moved in, and the reason why is unknown.

Ralph Lauren leased the house in January 1985 and opened his flagship store here on 21 April 1986. Since 2010 it has been a menswear shop, and the lease was renewed in December 2023 until 2034. The house has been one of New York's landmarks since 1976.

Fashion houses on Madison

Among the fashion houses that have shops on Madison Avenue, Wikipedia lists Ralph Lauren, Prada, Cartier, Gucci, Hermès and Burberry. The difference from Fifth Avenue is the scale: here the shops are smaller, the pavements calmer and the customers often neighbours. Between the shops are galleries, patisseries and the residential buildings that make the Upper East Side New York's most classic neighbourhood.

Bemelmans Bar at The Carlyle

At 35 East 76th Street, you'll find The Carlyle and Bemelmans Bar. In 1947, Ludwig Bemelmans, creator of the Madeline books, painted the mural Central Park with Madeline, her eleven classmates and their headmistress in the park through the year's four seasons. He did not charge money for it, but instead got to live at The Carlyle with his family for a year and a half, according to Wikipedia.

Breuer Building – from Whitney to Sotheby's

At 945 Madison Avenue stands Marcel Breuer's 1966 building, an inverted staircase in granite and concrete. Here, the Whitney Museum of American Art, The Metropolitan Museum of Art and The Frick Collection have in turn shown art. In November 2025, the building opened as Sotheby's global headquarters, restored by Herzog & de Meuron together with PBDW Architects, according to Designboom.

Walking Madison Avenue

Start at 60th Street and walk north. Stop at Ralph Lauren's mansion on 72nd Street, look in at the Breuer Building on 75th Street and finish with a drink at Bemelmans Bar on 76th Street – or walk one block west to the museums on Fifth Avenue. See the blocks in VERA PI's New York guide, on the map of Manhattan and with VERA PI Camera, and find more city guides among metromode.co's destinations.

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