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20 Vintage Photos Of New York City from the 1920s

Vintage Photos May 16, 2025

Last Updated on May 16, 2025 by Colby Droscher

Take a step back to 1920s New York City, a time when the city was buzzing with transformation. The skyline was evolving with towering skyscrapers, the streets were filled with the sounds of jazz, and the energy of the Roaring Twenties was palpable. From busy workers on lunch breaks to families enjoying Central Park, each image shows a different facet of the New York that was already beginning to shape the city we know today.

In these scenes, you can almost feel the rhythm of the city, its optimism, its grit, and its relentless march forward. While these photos are nearly a century old, they reveal a New York that continues to resonate in the pulse of the modern city, offering both a reflection of the past and a glimpse of what was to come. Here are 20 vintage photos of New York from the 1920s.

1. Structural worker in New York, 1920s

A construction worker wearing gloves and a cap fastens a steel beam high above New York City, with the Chrysler Building and East River visible in the background. The scene captures a sense of height and urban development.
juliuslammet

Safety harnesses weren’t necessary in the ’20s.

2. New York police officer hanging from a girder, 1920

A person in uniform hangs by one arm from a steel beam high above a busy city street, with cars and billboards visible below. The photo is black and white and appears to be from the early 20th century.
tesla_beats_edison

That wasn’t part of the job description.

3. The interior of a New York subway car in the ’20s

Passengers in early 1900s attire, including hats and formal clothing, sit on benches inside a vintage subway car. The car is lit with overhead lights, and an operator is visible at the far end near the door.
worldhub995

It’s surprising to see there were as many ads then as there are now.

4. New York chorus line girls, 1920s

Eight women in matching outfits stand in a line on a city street, each holding a sign with a letter or symbol that together spell “NEW YORK.” Behind them are classic brownstone buildings.
rockystl

The girl wearing the dot on the end drew the short straw.

5. The FDNY in 1920

A vintage black-and-white photo shows a group of firefighters in uniform posing with an old fire engine in front of a brick building on a cobbled street. Some men are seated on the vehicle while others stand beside it.
enclavesoldier

Thank God safety gear has made a significant increase since then.

6. A new biplane being paraded in New York, 1920

A vintage truck transports a biplane through a busy city street lined with early 20th-century buildings; people watch from sidewalks as drivers sit at the front of the truck.
hyhopes

The plane is being paraded down Fifth Avenue with its propeller in full gear. That guy on the back better watch his head.

7. Construction workers taking a break

Four construction workers relax and eat lunch while sitting on steel beams high above a city, with buildings visible far below; the scene captures a moment during high-rise construction in the early 20th century.
harleybug88

They look more comfortable here than I do in my own bed.

8. Daredevils were wild in the ’20s

A man in a suit balances on a chair perched on top of a table, both positioned on the edge of a tall building, with a city skyline visible far below.
elite_lucifer

He saw the skyscrapers in New York and said, “Let me cheat death up there.”

9. New York police officer doing a good deed, 1925

A vintage black-and-white photo shows a police officer directing traffic while a small black cat crosses the street carrying a kitten in its mouth among old-fashioned cars.
userdeleted

He stopped traffic to let this mama cat carry her babies across the street.

10. Shoppers flocking to a department store in Manhattan

Black-and-white photo of women walking past a hat shop window display, featuring mannequins with various hats. Sunlight streams through large windows, casting shadows on the busy street scene outside.
tyagi_rishu

Everyone wants to get their hands on one of those trendy hats.

11. A construction worker on a beam above Wall Street, 1920s

A construction worker balances on a narrow steel beam high above a city, carrying a large sack over his shoulder, with buildings and streets visible far below.
kornichon

No safety harness, and a giant sack of god knows what on his shoulder.

12. Teeing off from a skyscraper

A black and white photo shows one man swinging a golf club while standing on a steel beam high above a city, with another man sitting nearby, overlooking tall buildings in the background.
btmbrayer

I really hope there weren’t any unsuspecting patrons below.

13. Harlem 124th Street, 1920

A group of children, some jumping rope, play on a city sidewalk in front of brownstone buildings, while adults and other children watch from steps and windows. The scene is lively and full of energy. Black and white photo.
Zender44

I wish communities were as personal as they were in the ’20s.

14. A 1920s group selfie

Two black-and-white photos of a group of men in suits and hats standing on a rooftop, huddled closely together and taking selfies with an early box camera. The men are smiling and leaning toward the camera.
userdeleted

A selfie, before it was a selfie.

15. Painters atop the Woolworth building, 1926

Three construction workers balance on steel beams high above a city skyline, with tall buildings and smoke visible below, capturing the daring heights and danger of early skyscraper construction.
a420painter

That man in the far back has some serious balance.

16. Colorized photos of 1920s New York

A busy city street in the early 20th century with vintage cars, streetcar tracks, and people in period clothing walking and gathering on sidewalks. Buildings line both sides of the street.
emu_or_aardvark

Color makes this photo seem so much more relatable.

17. A New York Halloween, 1920

A group of people in costumes pose indoors; some are dressed as characters from "The Wizard of Oz," including the Tin Man, Cowardly Lion, and Scarecrow, with others in various hats and outfits. The photo is black and white.
pasargad

The costumes of choice for the ’20s were hobos, witches, and clowns.

18. Visiting NYC, 1920s

Three Black men in suits stand outdoors against a brick building. Two men wear dark suits while the man in the center wears a light-colored suit and hat. Each holds a hat in one hand and stands confidently facing the camera.
rockerswise

These men are Hope Howell, Leonard Howell, and Marcus Garvey.

19. Delivering ice in Lower Manhattan, early ’20s

Two women in overalls and hats use tongs to lift a large block of ice next to a horse-drawn wagon. Other ice blocks are scattered on the ground. The image appears to be from the early 20th century.
interdimentionaleyes

They would transport ice in massive blocks so it wouldn’t melt by the time it reached the city.

20. Photographer taking a photo of the NYC streets, 1925

A man in a suit crouches on the edge of a tall building, high above a busy city square filled with people and surrounded by early 20th-century skyscrapers. The view is dramatic and vertiginous.
blindwatchmaker88

Thank God commercial drones came into play, or we’d still be doing this.

Want to see more content from New York?

Check out 17 Vintage Photos of Swimming in New York City’s Outdoor Pools (1930-1960), or take a look at 20 Photos of New York City Then and Now. Finally, if you want to look into New York’s Five Points neighborhood, check out 19 Striking Photos of New York’s Five Points Slum (1880s-1900s).

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