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Photos That Capture the Wild Spirit of 1920s Flappers

Alina Wang 4-4 minutes 10/22/2025

Split image: Left, six women in 1920s flapper dresses pose with a police officer outside an L.A. Police Station. Right, a flapper sits thoughtfully on a bench in a garden, wearing a cloche hat and stylish dress.

Split image: Left, six women in 1920s flapper dresses pose with a police officer outside an L.A. Police Station. Right, a flapper sits thoughtfully on a bench in a garden, wearing a cloche hat and stylish dress.

They danced, they drank smuggled booze, and they rewrote the rules of womanhood. The flappers of the Roaring Twenties weren’t just following a fashion trend — they were the OG rule-breakers. With their bobbed hair, flashy dresses, and fearless spirit, these women defied everything high society expected of them, especially during an era when women were meant to be demure and soft-spoken.

From jazz clubs to speakeasies, here are more than 20 vintage photos that capture the flapper era in full swing.

1. Three Flappers Strike a Pose in Sparkly Evening Dresses

Three women in 1920s flapper dresses and heels stand in a row, smiling and holding each other, lifting one leg in a playful pose. The background features an arched doorway and patterned carpet.

StrawberryShortcakeL/Reddit.com

2. Day at the Beach: Flappers Show Off Their Matching Bathing Suits

Eight women in vintage 1920s swimsuits and swim caps sit on a bench at the beach, smiling and posing with their arms around their knees; a pier and building are visible in the background.

StrawberryShortcakeL/Reddit.com

3. ‘Flappers Pose With a Car in the 1920s’

Five women in 1920s flapper dresses pose cheerfully around a vintage car on a beach, with the sea and a ship visible in the background.

xXHarleen_QuinzelXx/Reddit.com

4. Flappers and Jazz Musicians Party Together at a Jazz Club

A group of women in 1920s flapper dresses sit in a row kicking their legs, while men kneel in front serving drinks; a violinist and a conductor stand behind, all in a lively, festive setting.

StrawberryShortcakeL/Reddit.com

5. A Group of Stylish Flappers Gossiping Together

A group of women in 1920s flapper-style dresses and cloche hats pose together outdoors, smiling and interacting, some seated and some standing behind them, with trees in the background.

StrawberryShortcakeL/Reddit.com

6. Flappers Gather ‘Round for Drinks and Laughter at a House Party

A group of women in 1920s attire laugh and pose around a dining table with food, drinks, and teacups, celebrating together in a warmly decorated room.

StrawberryShortcakeL/Reddit.com

7. A Line of Flappers Dressed to the Nines in Their Signature Style

A group of women in 1920s flapper dresses, cloche hats, and pearls stand on steps, smiling for a portrait. Their outfits feature dropped waists, ruffles, and decorations, typical of the Roaring Twenties fashion.

OtherwiseTackle5219/Reddit.com

8. ‘A Police Officer With a Group of Flappers Outside the Police Station in Los Angeles, Circa 1920’

A group of six women in 1920s fashion, wearing cloche hats, pose cheerfully around a uniformed police officer seated on a bench outside an L.A. police station. All are smiling and appear to be enjoying themselves.

TrendWarrior101/Reddit.com

9. A Candid Snap of a Flapper ‘Heading to a Party in the City, 1922’

A stylish woman in 1920s fashion, wearing a fur-trimmed coat, cloche hat, and heels, sits on the bumper of a vintage car adorned with badges. Another woman is visible inside the car.

OldPhotoArchive/Reddit.com

10. A Flapper Demonstrates How To Hide Booze During Prohibition

A woman in vintage clothing holds a book, then opens it to reveal a hidden compartment with a small bottle inside, demonstrating a secret storage book.

Electrical-Aspect-13/Reddit.com

11. Just Look at the Size of That Flask!

A woman in a vintage dress and fur coat reveals a hidden metal container strapped to her torso, likely used for smuggling alcohol during Prohibition. She stands indoors in a room with wooden paneling and a chair.

Electrical-Aspect-13/Reddit.com

12. If All Else Failed, There Was Always the Good Ol’ Boot Stash

A woman in 1920s attire, wearing a fur coat, hat, and boots, sits on a chair, smiling while adjusting her shoe. She is on a tiled floor with a swastika pattern visible near her feet.

Electrical-Aspect-13/Reddit.com

13. Can’t Forget About the Covert Shots Hidden in a Book

A woman in vintage clothing and a headscarf holds a flask labeled "Four Swallows" and appears to drink from a hidden straw, embodying a secretive or playful attitude in a black-and-white photograph.

Electrical-Aspect-13/Reddit.com

14. ‘A Group of Flappers Pose for a Close-up at a Football Game in Washington D.C.’

A group of stylish young women in cloche hats and dresses sit together on bleachers, watching an event. Other spectators, mostly men in suits and hats, are visible in the background. The image appears to be from the 1920s.

UserDeleted/Reddit.com

15. Three Flapper Friends Pictured in Oakland, California, Circa 1920

Three women wearing 1920s-style dresses, cloche hats, and heeled shoes sit on a low stone wall outside, smiling and posing for the camera. A house and picket fence are visible in the background.

Hooverpaul/Reddit.com

16. ‘My Great-Grandmother Rocking Her Best Flapper Style, Circa 1928 in Pittsburgh’

Sepia-toned photo of a young woman sitting sideways on a chair, wearing a dress and a fur stole, with short wavy hair and an elegant, confident expression. The background is softly blurred.

NoraMurphy927/Reddit.com

17. Only Flappers Could Make Tumbling Down the Stairs Look Cool

Five women in vintage dresses appear to have tumbled playfully down a staircase, sprawling in various poses with amused expressions, their arms and legs extending in different directions.

Pinkchickenman/Reddit.com

18. ‘Flappers Dancing the Charleston Atop the Sherman Hotel in Chicago, 1926’

Two women dressed in 1920s fashion balance playfully on the edge of a tall building rooftop, high above a cityscape of buildings, both smiling and striking dynamic poses.

Sleeeepy_Hollow/Reddit.com

19. A Flapper Lost in Deep Thought, or Maybe Just Planning Her Next Night Out

A woman in 1920s attire sits on a bench outdoors, resting her chin on her hand. She wears a cloche hat, sleeveless dress with a pleated skirt, and heeled boots, looking thoughtfully into the distance.

takecarfirst/Reddit.com

20. ‘Flappers Heading for a Day at the Shore’

Three smiling women pose on the front of a vintage car; one in a swimsuit sits on the hood with arms raised, while two in dresses sit on the fenders, all holding hands and celebrating outdoors.

OtherwiseTackle5219/Reddit.com

21. Flappers Defy Prohibition Laws by Chugging Bottles of Bootleg Alcohol

Four women in 1930s-style dresses stand in a row outside against a wooden wall, each drinking from a bottle and looking upward. They hold clutches or purses and are dressed in vintage fashion.

blrghh/Reddit.com

22. ‘1920’s Flapper Goes Full Bonnie and Clyde’

A woman in 1920s attire, wearing a dark cloche hat and gloves, stands facing the camera while holding two large pistols crossed in front of her chest, with a serious expression.

deftonechromosome/Reddit.com

Want more ’20s content?

A group of boys and young men gather around a vintage car with a broken front wheel on a city street in front of a large building. The scene appears to be from the early 20th century.

skatterbug/Reddit.com

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