Sidewalk Sashay Countdown: The Best Celebrity Street Style of 2015, Part 1

Posted on December 22, 2015

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Kittens, if you know anything about us then you know we couldn’t leave the celebrity-strewn sidewalks of the world uncommented-upon at the end of the year. If we’re rating the best and worst red carpet looks, we have a duty to rate how the stars did when they walked a stretch of sidewalk without a step-and-repeat. In other words, let’s all judge the best celebrity street style of the year. We choose not to do a worst celebrity street style countdown, just because we’d wind up bitching at people for wearing ratty t-shirts to the drug store and no one wants to hear that. For the purposes of this list, these stars had to NOT be on their way to or from a promotional appearance. Some of them are going to be way more dressed up than others, but that’s kind of what street style is all about. The range is so much wider than the red carpet. Subsequently, this list tends to be much more controversial than our red carpet countdowns.

Shall we get to it?

 

20. Emma Roberts in NYC

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Right out of the gate, we’re picking something about which we doubt we’re going to see much in the way of agreement. But her red carpet style kind of sucks and there’s something very real-world, strutting-with-my-besties charming about the look, even if the dress looks like something that belongs on a Peanuts character.

 

19. Lenny Kravitz in NYC

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We get that there’s not a lot to this look, but it’s so perfectly Lenny – and he looks so damn good in it – that we had to give it some end-of-the-year attention.

 

18. Taylor Swift in Los Angeles

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Tay had a very busy year, which means she didn’t have time to sashay up and down the streets of America in poorly matched thousand-dollar outfits like she used to. But she did manage to pull this look out of her hat, which we loved for having none of the prissiness of her East Coast looks and because she’s way more built for this kind of Southern Cali Boho than the Socialite Princess drag she tends to employ when she’s in New York.

 

17. Elizabeth Olsen in New York City

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Oh, there was much discussion and debate between T & Lo about this look. We didn’t love it when we first posted it, but Lorenzo rallied for it at the end of the year and argued vociferously for its chic coolness and on-point styling.

 

16. Jenna Dewan-Tatum in Hollywood

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Don’t look so pissed, Jenna! Not only did you make the Top 20, but you beat our Taylor Swift for wearing essentially the same look! It’s just a quirk of fate that we wound up with two white, lacey West Coast hippy-dippy looks on the same list and so close to each other. This one has way more of a summertime feel to it and we love it most for the way it’s styled. We might quibble about the hat but the shades and the sandals are perfectly chosen.

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