Twenty-three skidoo was a happening at a triangular site where Broadway and Fifth Avenue meet. The juxtaposition of the streets and a nearby park caused a wind-tunnel effect In the early twentieth century, men would hang out on the corner of Twenty-third Street and watch the wind blowing women’s dresses up, so that they could catch a little bit of ankle. This entered into popular culture and there are hundreds of postcards and illustrations of women with their dresses blowing up in front of the Flatiron Building. And it supposedly is where the slang expression “23 skidoo” comes from because the police would come and give the voyeurs the 23 skidoo to get them out of the area.
The now familiar distinctive triangular shape of the Flatiron Building, designed by Chicago architect Daniel Burnham and built in 1902, fills the wedge-shaped property. The 22-story iconic office building has been one of New York City’s most dramatic enduring symbols of the city since its birth. It was designated a New York City Landmark in 1966 and was added to the National Register of Historic Places in 1979, and designated a National Historic Landmark in 1989. It is popular with photographers, artists and illustrators.

View looking south (downtown) from the Empire State Building at part of the Flatiron District. The Flatiron Building is the triangular building at right center. To the left is the Met Life Tower, with Madison Square Park in front. Between the park and the tower, at street level, Madison Avenue begins at 23rd Street and runs uptown (toward bottom of image). Madison Square is the intersection in front of the Flatiron, where Fifth Avenue and Broadway cross. (Fifth goes to the right, Broadway to the left.) The trees of Union Square Park can be seen in the top left of the image.
The neighborhood around it is called the Flatiron District . The designation is of relatively recent vintage, dating from around 1985, and came about because of its increasingly residential character and the influx of many restaurants into the area. Before that, the area was commercial, with numerous small clothing and toy manufacturers, and was sometimes called the Toy District. Later, the toy businesses moved outside the U.S. and then the area began to be referred to as the Photo District—because of the large number of photographers’ studios and associated businesses located there, the photographers having come because of the relatively cheap rents.
Popular photographers like Stieglitz and Steichen photographed the building, along with artists and illustrators who all took the Flatiron as the subject of their work.
As of the 2000’s, many publishers have their offices in the district, as well as advertising agencies. The number of computer- and web-related start up companies in the area caused it to be considered part of “Silicon Alley” or “Multimedia Gulch”, along with TriBeCa and SoHo, although this usage declined considerably after the dot.com bubble burst.
Today, the Flatiron Building is frequently used on television commercials and documentaries as an easily recognizable symbol of the city, and in scenes of New York City that are shown during scene transitions in TV sitcoms and other shows and publications.
What is your favorite place in NYC? Have you visited the Flatiron District? Quite interesting with its museums, restaurants and shoppes.
Very cool, Gail. Thanks for the rundown! I haven’t spent much time in NYC. I can count the number of times I’ve been there on one hand. My most recent and memorable trip was with my hubby at Christmas time a few years ago when I brought my skates and fulfilled my life long dream of ice skating in Rockefeller Center. Next time, i want to skate in Central Park:-)
Paula, I can’t believe it. I actually met an ice skater that did Rockefeller Center rink. Just think of your audience. You had a moment of fame. Lucky you. Was it under the famous Christmas tree too? I love watching the skaters, especially from a front seat in the restaurant. How loverly . . .
Thanks for explaining 23 Skidoo, Gail. I haven’t been down to the Flatiron District for a few years. I love architecture, too, and want to gape like Gomer when I stand on the street, but that would “out” me as a tourist and set me up as a “mark.” That’s what I’ve been told anyway. Still, with all those glories built to inspire awe on display, I’m not supposed to look? I love Grand Central, too, and once spent an afternoon there between the exhibits, the shops (Posman Books is a fave) and the food court.
Rhonda, no place like New York. Well, if you gape at the buildings, it could also mean you are studying architecture. I did, and I lived to tell. Yeah, Grand Central is gorgeous, especially with its new look by John Canning. His crew came to Lockwood and brought the library back to life. Back to it’s original glory. It is astonishing as is Grand Central.
I always wondered where that expression came from. I love the Flatiron. It’s hard to pick one spot in the City. St Pat’s comes to mind. Rockefeller Center, the UN, the Metropolitan Museum bring back fond memories. And then there’s Brooklyn.
Marian, thanks for visiting. It is hard to choose. There are so many that I love, mostly all of them. The illustrator, James, that I have on my blog, is drawing every building in NYC. I just bought his book, all the buildings in NYC that he has drawn so far, and it only cost $13.50. Love it. Each building has a personality. Did you ever see the Lipstick Building. HA, that a fun piece of architecture. St Pat’s fascinates me. It is a traditional church, everytime I visit, I am amazed at the architectural features. It is a gorgeous church. By the way, have you been to Barcelona yet. You have to go to see the church Antonio Gaudo designed and partially built, and they are still building. Did I blog about that one yet? I have to check. It has the most fascinating history. Anyway, I could blog just about architecture everyday. Each place has it’s stories too, you know, the people. Usually I talk about design, so it’s a stretch and a journey for me, to do the social aspects of a building.
Grand Central Station is one of my favorite buildings, Gail. And the Woolworth building, where my publisher is housed. One of the most amazing lobbies ever!
Kristan, good to see you here. Thanks for commenting. Grand Central Station was renovated by the same company, John Canning, that renovated the library at our Lockwood-Mathews Mansion Museum in Norwalk, CT. Both done with panache and skills. The Woolworth building is handsome. But the public lobby is amazing as you mentioned, is richly decorated with heavily veined marble from Greece and marble floors from Vermont. Designers, artists, and sculptors were hired to make the building lobby absolutely extraordinary. All that in contrast to the frugal philosophy of the Woolworth five and ten cent stores.