Brad Pitt 1 of 10Brad is sportin’ some retro style in this vest and jacket khaki ensemble with matching fedora. The addition of scraggly facial hair makes Brad’s transformation from conventionally handsome to hunky hipster complete.
Will Brad and Angelina ever get married — at least for the kids? »
Maggie Gyllenhaal 2 of 10Maggie was one of the first celebs to embrace the one-piece look, wearing this specific outfit in 2008. See, she was totally into jumpsuits before they went all mainstream.
Check out what Maggie Gyllenhaal thinks about raising a kid in the city »
Michelle Williams 3 of 10We can’t tell if this is Michelle’s new style choice or if she’s trying to blend in with the sea of bespectacled, wool-cap wearers out there to hide from paparazzi, but she’s definitely embracing the hipster look full on! We even spot some plaid (and a pirate umbrella!) on little Matilda.
Michelle Williams gains weight to play Marilyn Monroe »
Natalie Portman 4 of 10When not dressed to the nines on the red carpet, Natalie seems to prefer a more secondhand style. And knowing how food-conscious this vegan Oscar-winner is, we’re betting that apple is
Will Natalie Portman retire from acting to be a SAHM? »
Johnny Depp 5 of 10The hat, the shades, the leather jacket … the plaid shirt tied oh-so-casually around his waist — you can almost sense the Captain Jack Sparrow swagger and nonchalance as he stops to
sign an autograph.
Johnny Depp won't act nice for his daughter's boyfriends? »
Kate Hudson 6 of 10Kate wears vibram five-finger shoes while out and about on her bike — the better to feel the earth while she saves it with this eco-friendly choice of transportation.
Will a nasty prenup end Kate Hudson and Matt Bellamy's relationship? »
Gwen Stefani 7 of 10Harem pants sighting! We wondered which celeb would be the first to strut around in this hip new trend, and Gwen did not disappoint … wearing a plaid print, belt askew, and hair piled on top of her head to complete the ensemble.
Gwen Stefani brings her Harajuku line to Target »
January Jones 8 of 10It’s ironic that January Jones was such a fan of the high-waisted jeans trend before she got pregnant with her first baby. To the post-baby set, these are often just referred to as “mom jeans.” Cool bowling shoes though, Jan.
January Jones back on set less than a month after pregnancy »
Ashlee Simpson 9 of 10Who needs pants? Not this celeb! Ashlee goes with the black leggings and shirt combo (a baggy plaid shirt, of course) for day strolling around the town.
Are Ashlee Simpson and Pete Wentz back together for their son? »
Madonna 10 of 10Always fashion forward, Madonna offers her own take to the hipster look with bold black boots paired with a flowy scarf and hat tilted to the side.
Is Madonna aging appropriately? »