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34 Vintage Photos From the Late 1920s

Rachel Schneider 4-5 minutes 9/10/2025

Left: Two women in 1920s attire smile while stirring a large pot outdoors. Right: A man stands by a vintage car with a sign saying, “I’m not a Bootlegger. Don’t shoot, I’ll stop.”

Left: Two women in 1920s attire smile while stirring a large pot outdoors. Right: A man stands by a vintage car with a sign saying, “I’m not a Bootlegger. Don’t shoot, I’ll stop.”

The roaring ’20s weren’t all flapper girls at speakeasies. The latter half of the decade was still very much a simple time, with families spending quality time together, bootleggers trying to hide alcohol, and students packed into classrooms like sardines. These pictures depict the late 1920s, transporting us back in time.

1. Passengers Watching an In-Flight Film on an Imperial Airways Flight (1925)

Six men with short hair, wearing coats, sit in wicker seats inside an old-fashioned vehicle or aircraft, facing forward toward a partition with windows. Overhead racks hold bags, and daylight comes through side windows.

John-Piece / Reddit.com

2. Car Accident With a Postal Truck and a Tree in Boston (1927)

An old-fashioned U.S. Mail delivery truck with a broken front axle leans into a tree on a quiet city street, while another vehicle is parked further down the road.

UserDeleted / Reddit.com

3. Sibling Love (1926)

Four young children pose for a formal portrait; three boys stand behind, dressed in suits and sailor outfits, while a baby sits in front on a chair, wearing a light gown. The photo appears vintage and sepia-toned.

leejtam / Reddit.com

4. Little Girl With Her Doll (1925)

A young Black girl in a dress stands indoors with one hand on her hip and the other on a vintage stroller holding a doll. The photo has a sepia tone and appears to be from the early 20th century.

UserDeleted / Reddit.com

5. Hanging Out at Venice Beach (1927)

Three young adults in vintage swimsuits pose playfully; two women, one on each side, touch the chin and cheek of a smiling man standing between them. Both women wear heels. Outdoor setting, likely from the early 20th century.

DynastyFan85 / Reddit.com

6. Kids on Bourbon Street in New Orleans (1925)

Four children watch a man with a street organ on a cart at a city intersection, while another man in a suit and bowler hat stands nearby; historic buildings and power lines are visible in the background.

UserDeleted / Reddit.com

7. Sun Rays at Grand Central Station (1929)

Black and white photo of Grand Central Terminal, with sunlight streaming through large arched windows and illuminating people walking and standing in the spacious hall.

Bulmara / Reddit.com

8. Michelin Mascot Standing Next to an Advertising Vehicle in Santa Clara (1926)

Vintage black-and-white photo of a person in a Michelin Man costume, a man in a suit and hat, and a child sitting inside a tire. They're posed in front of an old vehicle with Michelin ads on the side.

Then-Guarantee-6445 / Reddit.com

9. Lumber Truck Smuggling Alcohol (1926)

Three men inspect the back of a truck filled with stacked wooden planks concealing an opening, suggesting hidden contraband. The background shows signage for hoses, belting, and packing supplies.

deathakissaway / Reddit.com

10. War Veteran Selling Matches on the Street in Canterbury, Kent (1928)

An elderly man with a white beard wearing a red uniform with gold epaulets and a black top hat sits on a step beside a brick wall, with a cane and a basket of assorted items at his side.

UserDeleted / Reddit.com

11. Christmas Eve in Warsaw (1926)

A vintage black-and-white photo shows a family of four sitting around a small table, sharing a meal. An upside-down Christmas tree hangs from the ceiling, decorated with candles and ornaments.

szymon362 / Reddit.com

12. Totally Not a Bootlegger (1929)

A man stands beside an old car with a sign on the back that reads, "I'm not a Bootlegger. Don't shoot. I'll stop." The scene appears to be from the early 20th century, in a residential neighborhood.

InfamousLeopard383 / Reddit.com

13. Second Grade Classroom (1927)

A black-and-white photo of a vintage classroom with dozens of young students, mostly girls, seated at wooden desks, facing the camera. The room has chalkboards filled with writing and charts on the walls.

AlmanzoWilder / Reddit.com

14. Taking Ducklings for a Swim in Washington, D.C. (1927)

Two women dressed in 1920s-style clothing sit on a curb, holding leashes attached to ducks swimming in a large container. In the background, two young girls in hats stand on the sidewalk.

blrghh / Reddit.com

15. Woman With Her Baby in a Wooden Pram in the Netherlands (1929)

A woman in traditional Dutch clothing and wooden shoes stands next to a small child seated in a wooden cart outside a dark wooden house with brick foundation. Both are smiling, and the setting appears historic or early 20th century.

theanti_influencer75 / Reddit.com

16. Drexel Institute Girls’ Rifle Team (1925)

Seven women in 1920s-style clothing stand outdoors, holding rifles. The group is posed in a line, with serious expressions, in a yard with bare trees and buildings in the background.

UserDeleted / Reddit.com

17. Boys Playing in a Wagon in Pittsburgh, Pennsylvania (1925)

Three young boys sit together on a small wagon on a city street, two Black and one white, with the white boy hugging the other two. Vintage cars and blurred figures are visible in the background.

UserDeleted / Reddit.com

18. Celebrating on New Year’s Eve (1929)

A large group of people dressed in formal and festive clothing poses closely together at a lively party, many smiling, holding drinks, and wearing hats or masks, suggesting a celebration or costume event.

UserDeleted / Reddit.com

19. Native American Girl Holding a Baby at a Train Station (1929)

A young Native American woman in traditional dress stands on wooden planks, holding a small child in her arms. The background shows railroad tracks and blurred figures.

UserDeleted / Reddit.com

20. Macedonian Farmers in Traditional Dress (1926)

A man and woman in traditional Eastern European folk costumes stand outdoors near tall, bundled wheat stalks, with mountains visible in the background. The woman wears a patterned apron and headscarf; the man wears an embroidered vest and hat.

UserDeleted / Reddit.com

21. Couple’s Engagement Photo in Kokomo, Indiana (1927)

A black and white vintage photo of a man in a suit and tie sitting next to a woman in a cloche hat and 1920s dress, both smiling and posing for a formal portrait on a bench.

shle896 / Reddit.com

22. Making a GIANT Pot of Soup (1925)

An older woman in a long dress and apron stands outdoors stirring a steaming cauldron over a fire, surrounded by trees and a rustic wooden fence in the background.

RyanSmith / Reddit.com

23. Native American Family in Their Tipi in Montana (1927)

Five Indigenous people sit inside a tent decorated with patterned fabric. They wear traditional clothing and beadwork, and are seated on patterned blankets, with crafts and textiles around them.

AlleyBarber / Reddit.com

24. Old School Air Travel (1928)

Black and white photo of passengers sitting in wicker seats inside a vintage airplane, facing forward. Some wear hats, and there are hats and bags stored on overhead racks. The cockpit is visible at the front.

CinnamonDish / Reddit.com

25. Solarium for Sunbathing (1929)

Two women in towels stand at the entrance of a “Ladies Only” solarium. Above the door, a sign reads, “Let the sun bathe your body – curative, life giving.” The scene appears vintage, in black and white.

Dhorlin / Reddit.com

26. Chicago Wedding Party (1927)

A vintage black-and-white photo of four women in dresses and three men in suits, one wearing a top hat, sitting and standing in a formal group pose, holding bouquets, in front of a dark curtain.

aperson7780 / Reddit.com

27. Mother and Daughter in Their Kitchen in Manitoba (1929)

Two women in a rustic kitchen, one placing a pot on a vintage wood-burning stove and the other smiling while holding firewood, with pots and utensils visible on shelves and hanging from the wooden walls.

OtherwiseTackle5219 / Reddit.com

28. The LA Public Library Bookmobile Program for the Sick (1928)

A woman selects a book from a wheeled library cart for a patient who is lying in a hospital bed, reading. The scene appears to be from an earlier historical period.

UserDeleted / Reddit.com

29. Cambridge Students Out for a Stroll (1926)

Two men in 1920s attire walk down a city sidewalk. Both wear baggy pants tucked into high socks, jackets, collared shirts, and ties. One wears a fedora, the other a flat cap; a cyclist rides in the background.

UserDeleted / Reddit.com

30. Tower Bridge in London on a Foggy Morning (1928)

Several people stand on a pebbly riverbank near the water, feeding swans, with London’s Tower Bridge visible in the misty background.

UserDeleted / Reddit.com

31. Backyard Hangouts (1926)

Four people and a dog pose outdoors by a bench and a tree. Two women sit on the bench, one smiles and wears a headband, the other looks at the dog. A smiling young woman stands behind the dog, with a young man seated at right.

mashkaromanova / Reddit.com

32. Mobile Library at the Rockville Fair in Maryland (1928)

Two women stand by a vintage truck with shelves of books and a sign reading “County Library: We Want One” at an outdoor fair. Old cars and trees are in the background.

UserDeleted / Reddit.com

33. Toddler Playing Outside (1928)

A smiling baby in a light dress sits on a vintage tricycle outdoors, with a building and a low wire fence in the background. The photo is in black and white, giving it a nostalgic feel.

amusesings / Reddit.com

34. Woman at the Entrance to One of Bordighera’s Gardens in Italy (1928)

A woman in a blue dress holding a bouquet stands in front of a rustic wooden door framed by a stone wall and covered with abundant pink flowering vines.

GoodGriefWhatsNext / Reddit.com

More ’20s content:

youngvein/Reddit.com

youngvein/Reddit.com

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