The Ten Best Celebrity Street Style Looks of 2016

Posted on December 30, 2016


Kittens, in recent years, the sidewalks of the great cities of the world have become almost as important to celebrity self-promotion as a red carpet and almost as effective a way for fashion brands to promote their wares as a runway. In other words, the celebrity street style game has intensified tremendously. Gone are the days when we could act bemused over Tay Swift’s or Reese Witherspoon’s rather obviously fake sashays. Now, everyone’s doing it.

But for the purposes of this collection of looks, we decided to pick at least a few that were more about style than labels. Admittedly, it wasn’t easy, since celebrity street looks are almost as styled as their red carpetry. Even so, the following represent, to us, the very best of celebrity sidewalk sashay style in 2016, which is as much about making an impact for the paparazzi than it is about looking chic in a traditional way. And since celebrity style has become so conformist in recent years, we tried to pick a few just for being a little odd.

Take it away, streetwalkers.


10. Joel Kinnaman in New York City

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Because “Hot Swedish Security Guard” fantasies are a thing.

For us, anyway.



9. Sienna Miller in NYC



Yeah, it’s Sienna Miller and yeah, she’s wearing leather shorts and open-toed booties, but this one really worked on us over time. We rolled our eyes a little at first glance, but the more we considered it, the more we liked it for its sassy, modern take on a Chanel street look.



8. Eva Green at Heathrow

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Because if you can get away with “defecting Soviet ballerina” drag, you should do so at every opportunity. Talk about playing to your strengths.



7. Jennifer Lopez in NewYork City

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Some of J Lo’s street wear can be pretty over-the-top, which is why we responded so well to this look. It’s very her, it looks great, but most important for us, it has a low-key chicness that’s a bit refreshing coming from Jenny’s corner.



Famke Janssen in New York City

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We have our quibbles with the skirt, which looks like sheer drapes to us, but the sweater, hat, shades and shoes are all so damn cute. It helps that her hair flip game is so on point.



5. Janelle Monae at LAX
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Because nobody flies like this, but everybody should.



4. Rihanna in New York City

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Admittedly, we have serious issues with the bag and shoes, but Miss Ri simply can’t be beat in the game of bringing high drama to the street through the deployment of some questionable style choices. The gorgeous caftan, face and hairstyle all sell the hell out of this look.



3. Celine Dion in Paris

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Madame had a terrible year, what with the death of her beloved husband René in January. But she rebounded in a way that we can only applaud: By jetting off to Paris, putting on couture, and walking the streets of the City of Lights, soaking up the love from the locals. We can’t think of a better way to pick yourself up after a Bad Thing. And it helps that she’s never looked so chic in her life.



2. Lupita Nyong’o in Toronto



We fully admit that if Taylor Swift stepped out in such a matchy, high-label (Valentino) sidewalk look, we’d probably be a little bit bitchy about it, but our entire philosophy of high style maintains that the garment or accessories are only part of the equation. The wearer and venue are just as important for good style choices to work. She looks fresh and pretty without attempting to be precious about it. It’s a look that plays to her strengths and she knows exactly what to do with it.



Lady Gaga in Paris



We swear we didn’t pick this just to piss you off. No, really. But in terms of sheer head-turning fabulosity; in terms of picking the exact right look for your surroundings; in terms of knowing what your fans and the press expect from you, this girl NAILED IT. When we hear the words “Lady Gaga in Paris” this is the kind of thing we want to see – and the kind of thing she almost never pulls off as well as she is here. She looks amazing and unique, which is the whole Gaga style brief wrapped up in two words.

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