The Best Celebrity Bobs in the History of Hair

Bob haircuts are having a moment. And we're not talking lobs. Lucy Hale's bob has flown slightly under our radar, but with the final season of "Pretty Little Liars" imminent, all eyes are on the stars, and it's Hale's jaw-length blunt bob that we've been fixated on.

Lucy Hale with a bob

And now Selena Gomez, who cropped her hair to a transitional lob length last December, has gone for a sassy take on a bob; it's very early '90s Winona Ryder.

Selena Gomez with a bob

While the bob is having a mini resurgence, from the Marcel-waved bobs of the Gatsby era to Taylor Swift’s edgier take on things, it has proved to be one of the most timeless looks of all time. Karlie Kloss, Kim Kardashian West, Rihanna, Victoria Beckham, and Beyoncé have all flirted with the cut and all to iconic effect.

But who’s top of the bobs? Whose chop has had the most enduring influence, and who changed the game with their face-flattering cut? To help us rank the best bobs in history, we’ve recruited celebrity stylist, Charles Worthington brand ambassador, and all-around hair guru Ken O’Rourke.

Ready to find your short-hair icon? Keep scrolling for all the timeless bob inspiration.

Louise Brooks

Louise Brooks with a bob
John Kobal Foundation / Getty Images

The ultimate bob icon, Louise Brooks was one of the first to sport the haircut, sparking a revolution amongst the flapper set. “This is the 1920s bob—classic, iconic and copied by millions,” O’Rourke says. “This looks fantastic on oval-shaped faces.”

Debbie Harry

Debbie Harry with a tousled bob
Roberta Bayley / Getty Images

The tousled bobs of today likely have Debbie Harry and her rebelliously messy blunt cut to thank. A pioneer of heavily textured roll-out-of-bed-and-rock hair, the Blondie singer’s peroxide chop sparked a million imitations.

Karlie Kloss

Karlie Kloss with a bob and fringe combo
Venturelli / Getty Images

Karlie Kloss swapped her supermodel long locks for a chin-skimming bob in 2012, inspiring fellow squad members Taylor Swift and Kendall Jenner to eventually go for the chop too. “I love this look on Karlie—roughed up, tousled, loose texture that looks completely effortless and natural. It’s unpretentious and casual—the less you try and make it look great, the sexier it looks,” O’Rourke says.


Beyonce with a bob
Jon Kopaloff / Getty Images

When Beyoncé, queen of the voluminous stage hair, stripped her look back to a super-short pixie cut, we thought we’d seen her most iconic hair moment ever. Then came the sassy wavy bob, closely followed by mainstream use of “wob”—nobody nails a trend quite like Queen Bey.

Linda Evangelista

Linda Evangelista with a retro bob
Venturelli / Getty Images

One of the original ’90s supers, Linda Evangelista has become a hair chameleon over the years, but it’s her classic bob that has gone down as her most iconic look. “She’s an amazing supermodel with a face that suits anything,” O’Rourke says. “The iconic look that I will never forget is the cover she did for Harper’s Bazaar. It was a super-sleek bob with a high-shine finish.”

Alexa Chung

Alexa Chung with a textured bob
Jeff Spicer / Getty Images

Though she likes to flirt with shoulder-length tresses from time to time, Alexa Chung always goes back to the bob—and we can see why. Famously cut by London-based stylist George Northwood, the Alexa is among the top requests from his clients and even inspired the Bob Bar in his Wells Street salon.

Lily Collins

Lily Collins with a wavy bob
Jeffrey Mayer / Getty Images

“Lily has a chin-length bob with a medium texture, and she looks great with her hair scraped back into a side parting or low chignon,” O’Rourke says. Another star who went for the dramatic long to short transformation, the actress chopped her tresses in 2013 and hasn’t looked back.

Gwyneth Paltrow

Gwyneth Paltrow with a sleek bob in The Royal Tenenbaums
Rex / Shutterstock

When it comes to hair moments in history, Gwyneth Paltrow’s "The Royal Tenenbaums" bob is one of them. Revered by the fash-pack, Gwynnie’s sleek blunt bob regularly finds itself pinned to fashion week mood boards, hailed as the epitome of covetable late ’90s style.

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