The Best Bobs Of All Time – Essence

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

Whitney Houston

Mary J. Blige

Cicely Tyson

Donna Summer

Prince

Naomi Campbell

Lena Horne

Eve

Rihanna

Lil’ Kim

Kelly Rowland