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The Best Bobs Of All Time – Essence

Connie Marie by Connie Marie
April 10, 2026
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The Best Bobs Of All Time – Essence
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So much can be said in such a short style. Bobs are cropped and chic, a symbol of power and rebellion—and the cousin of the pixie cut. But, while bobs were the best known short haircut style in the 1920s, it was a cut that was originally seen as scandalous. At the time, long hair was the standard of femininity, which meant bobs were a protest against the norm—to the point where many hairdressers outright refused to cut them. So, instead, off to the barber they went.

Credited to the ballroom dancer Irene Castle in 1915, the “Castle cut” was originally for convenience before the dancer underwent surgery. But, once the blunt, earlobe-length style picked up traction, especially among Flappers, hairdressers could no longer resist the economic boom of bobbing. They were all over hairdresser magazines, hair shops quadrupled, and the cut went on to define beauty for Ages. 

We’ve famously seen the cut in decades to follow. In 1970, Diana Ross had a notable departure from voluminous curls to a shoulder-length bobs. Then, Whitney Houston’s curled cuts were undoubtedly the look of the ’80s. This was, of course, Naomi Campbell’s bob symbolized the sheer power she held throughout the ‘90s. All that to say, it’s a cut that’s survived over 100 years and, in 2026, it’s still living on as a favorite cut this season.

Ahead, to inspire your spring styles, take a look at the best bobs of all time.

Diana Ross

American singer Diana Ross attends her birthday party in New York, New York, March 25, 1975. (Photo by Oscar Abolafia/TPLP/Getty Images)

Whitney Houston

American singer and actress Whitney Houston attends The Grammy Awards on March 2, 1988 at Radio City Music Hall in New York City, New York. (Photo By Larry Busacca/Getty Images)

Mary J. Blige

Mary J. Blige (Photo by Ron Galella/Ron Galella Collection via Getty Images)

Cicely Tyson

UNSPECIFIED – CIRCA 1970: Photo of Cicely Tyson Photo by Michael Ochs Archives/Getty Images

Donna Summer

Donna Summer (Photo by Ron Galella/Ron Galella Collection via Getty Images)

Prince

Musician Prince attending 30th Annual Grammy Awards at Radio City Music Hall in New York City, New York, United States, 2nd March 1988. (Photo by Vinnie Zuffante/Getty Images)

Naomi Campbell

Naomi Campbell (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)

Lena Horne

LOS ANGELES – 1943: Lena Horne poses for a promotional shot for the film “I Dood It’ directed by Vincente Minnelli in 1943 in Los Angeles, California. (Photo by Michael Ochs Archive/Getty Images)

Eve

Eve during V-Day Harlem 2002: V-Day’s 2002 Benefit Show In NYC Presented By Essence at The Apollo Theatre in New York City, New York, United States. (Photo by Jim Spellman/WireImage)

Rihanna

NEW YORK – OCTOBER 09: Rihanna arrives at the 2007 Cipriani Wall Street Concert Series at Cipriani Wall Street on October 09, 2007 in New York City. (Photo by James Devaney/WireImage)

Lil’ Kim

Lisa “Left Eye” Lopes and Lil Kim (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)

Kelly Rowland

Kelly Rowland. (Photo by Stephane Cardinale/Corbis via Getty Images)



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