Vintage Photos From The 20s That Prove Your Grandparents Could Party

Vintage Photos From The 20s That Prove Your Grandparents Could Party


July 19, 2025 | Alex Summers

Vintage Photos From The 20s That Prove Your Grandparents Could Party


Cultural Revolution

Ever wonder when America first learned to really let loose? The 1920s are said to have been this nation’s greatest cultural awakening. These snapshots of people and moments bring alive the energy of a legendary era.

Josephine Baker  - Intro

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Charleston Dance Contest

Have a look at flappers enjoying themselves while musicians play brilliant pieces during a Charleston dance contest at New York's Parody Club in 1926.

Crazy Flappers- 3224976Hulton Archive, Getty Images

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Ziegfeld Girls Jazz Band

This was an all-female jazz band associated with the famous Ziegfeld Girls. They were the chorus girls and performers in the Broadway revue productions known as the “Ziegfeld Follies”.

Women's Jazz Band-542415889ullstein bild Dtl. , Getty Images

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Flapper Dancing At Brighton Beach

The focal point is a young woman, dressed in full flapper fashion, dancing energetically atop a jazz band’s upright piano set up on the sandy beach. Surrounding her is Benny Krueger’s jazz band.

Flapper Dancing -515403732Bettmann, Getty Images

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Charleston Champion After Seven-Hour Dance

Miss Hardie was notably recognized as the ladies' solo Charleston champion around 1925 after dancing the Charleston for a record seven hours. In addition to this fame, Hardie was also active in sports, specifically tennis.

Charleston Champ - 78241991American Stock Archive, Getty Images

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Fashions At Nyngan Picnic Races

By the late 1920s, hemlines reached their shortest point of the decade, often just below or at the knee, especially for day and sporty events. This was a daring change compared to earlier decades.

File:Fashions at Nyngan Picnic races - Nyngan, NSW, between 1927-1930 by unknown photographer from The State Library of New South Wales.jpgUnknown, compiled by Alan Davies, Wikimedia Commons

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Exterior Of Harlem's Cotton Club

Look at the exterior nighttime view of the marquee of the Cotton Club nightclub in New York City from the early 1930s. The signage prominently advertises performances by Bill Robinson and Cab Calloway.

Cotton Club Marquee -74259389Michael Ochs Archives, Getty Images

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Krazy Kat Speakeasy Entrance

The Krazy Kat Klub was a real speakeasy in Washington DC, during Prohibition. It was named in homage to George Herriman’s influential comic strip Krazy Kat, which ran in newspapers from 1913 to 1944.

File:Krazy Kat LOC npcc.04658.jpgNational Photo Company Collection. Attributed to The Washington Times, July 31, 1921, Wikimedia Commons

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Group Portrait Of Women Posing

These women are dressed in contemporary 1920s attire, offering a clear and candid view of everyday women’s fashion from the period. They are posing near the entrance of a house.

File:Group portrait of women posing near the entrance of a house, c 1925 (7994873803).jpgAustralian National Maritime Museum on The Commons, Wikimedia Commons

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Fairbanks And Pickford

Here is a black-and-white portrait of the iconic American actors Douglas Fairbanks (1883–1939) and Mary Pickford (1892–1979). Their marriage on March 28, 1920, was widely publicized, and they were hailed as “Hollywood Royalty”.

File:Douglas Fairbanks and Mary Pickford 02.jpgUnknown (Bain News Service, publisher), Wikimedia Commons

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Harlem Entertainers Dancing At Small's Paradise Club

Small's Paradise Club was famed for its racially mixed crowd, Charleston-dancing waiters, and exciting floor shows. It competed with other Harlem venues such as the Apollo Theatre and the Cotton Club.

Dancers At Small's Paradise Club -515561556Bettmann, Getty Images

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Jazz cornetist Bix Beiderbecke And The Wolverine Orchestra

The Wolverines formed in 1923, taking their name from the Jelly Roll Morton tune "Wolverine Blues”. Bix Beiderbecke joined the troupe later that year.

Bix Beiderbecke -1068584678Donaldson Collection, Getty Images

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Henry Halstead Orchestra

This orchestra was led by Henry Halstead (1897–1984), a well-known American bandleader recognized for his influential jazz and dance band throughout the 1920s and 1930s.

File:Henry Halstead 1927.jpg6turn4back, Wikimedia Commons

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Club Holds Radio Dance Wearing Earphones

In an early example of music technology meeting social life, participants danced while wearing earphones to music broadcast from a band playing two miles away.

File:Club holds radio dance wearing earphones 1920.jpgUnknown authorUnknown author, Wikimedia Commons

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Louis Armstrong With King Oliver's Creole Band

One of the most well-known early jazz bands was Oliver's Creole Jazz Band, which came from New Orleans and had a huge impact on Chicago. Their recordings were made primarily at the Gennett studio in Richmond.

Louis Armstrong With The King Oliver's Creole Jazz Band -525524954Stefano Bianchetti, Getty Images

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The Five Aces Jazz Band

The Five Aces represent a type of popular small jazz band active during the Roaring Twenties, performing dance-oriented jazz at venues that defined the era’s musical and cultural scenario.

The Five Aces -2659116Topical Press Agency, Getty Images

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Frank Farnum Instructs Pauline Starke

Franklyn Farnum, the beloved silent-era Western actor often credited as "Frank Farnum," had a career dominated by Westerns and other film work. Here, he is seen beside Starke doing the Charleston.

Frank FarnumNational Photo Company Collection, Wikimedia Commons

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Jack Pickford And Marilyn Miller

Jack Pickford was a notable silent film actor and the younger brother of Mary Pickford. Scandals and personal struggles often overshadowed his career. The two got married on July 31, 1922, at Pickfair.

File:Jack Pickford & Marilyn Miller.jpgGeorge Grantham Bain Collection (Library of Congress), Wikimedia Commons

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Edwin J McEnelly's Orchestra

The image shows the 13-piece orchestra led by Edwin J McEnelly, active around 1922. His orchestra became famous for its lively jazz, waltz, and dance music styles.

Edwin J. Mcenelly's Orchestra C. 1922Unknown author, Wikimedia Commons

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Flapper With Garter Flask In Washington

Here, we see Mlle Rhea, a dancer from 1926. She is modeling a garter flask. This reflects a Prohibition-era trend where women discreetly carried flasks of alcohol.

File:Latest thing in flasks. Mlle. Rhea, dainty dancer who is now in the city as part of the Keiths program inaugurates the garter flask fad in Washington LCCN90709355.jpgNational Photo Company Collection, Wikimedia Commons

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Kid Ory

Kid Ory was a pioneering American jazz trombonist, bandleader, and composer. He is regarded as one of the earliest and most influential figures in New Orleans jazz.

File:Kidory.pngOkeh Records, Wikimedia Commons

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Portrait Of Louise Brooks

In this photo, we see the actress Brooks's distinctive dark, bobbed haircut with straight bangs. She popularized this style and soon became emblematic of the flapper period.

File:Louise Brooks ggbain.32453u.jpgBain News Service, publisher., Wikimedia Commons

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Dance Lesson For Basketball Players

Miss Vivian Marinelli is seen conducting a lesson in the Charleston dance to basketball players at Washington, DC's Palace Club. The men are identified as Jones, Conway, Grody, Saunders, Kearns, Glascoe, and their manager, Kennedy.

File:Miss Vivian Marinelli giving lesson in dancing the Charleston to basketball players of Washington, D.C.'s Palace Club- Jones, Conway, Grody, Saunders, Kearns, Glascoe, and Manager Kennedy LCCN89714359.jpgNational Photo Company Collection, Wikimedia Commons

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1920s Fashion For Young Flappers 

This picture shows two young women posing with a small tree, taken in San Francisco around 1923. Loose, straight-cut dresses generally made up the flapper look.

File:1920s Fashions for young Flappers in San Francisco.jpgJohn Atherton, Wikimedia Commons

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Josephine Baker Dancing The Charleston

Josephine Baker, an iconic African American-born French dancer and entertainer of the Jazz Age, is captured mid-movement, displaying the energetic and exuberant style of the Charleston dance.

File:Baker Charleston.jpgWalery, Polish-British, 1863-1929, Wikimedia Commons

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Bee Jackson, The World Charleston Champion

Bee Jackson played a very important role in popularizing the Charleston dance. Born in Brooklyn, she learned the dance after seeing the 1923 Broadway revue Running Wild.

File:Bee Jackson, 1926.webpUnknown author, Wikimedia Commons

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