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I would liken modern day street style to Version Two of the original hipster. Before it was PBR, flannel shirts, and shitty music. Now it's clothes that don't fit properly and an inflated sense of ironic humor. The primary similarity being that both groups come with their own trust funds.
Let's analyze one of these contemporary clusterfucks.
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From top to bottom.
A hat with ears like nubs. It's cutesy and juvenile, and screams "daddy issues."
Fox or rabbit fur coat. Announcing that money is no object, or at least that an ugly jacket is far more important than meals for three months. I think the assumed elegance of a fur coat was intended to negate the preschool cap.
From what I can tell her bottom is a Nike tennis skirt. It signals the aloofness or the upper class in New York City, and supports function and form.
Black tights, because shit's cold, yo'.
Finally, in a failed climax, high-top metallic sneakers. A nod to carefree youth and transcendence of cultural boundaries.
What this all amounts to is jack shit.
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Street style is intended to look like the wearer spent minimal funds and effort to compile his or her choice outfit. In reality, we all know that the individual pieces of the outfit were incredibly pricey (because cost trumps style and quality) and an immense amount of time was put in to selecting the items which clashed the most. The outcome is still the same, rolling around on the closet floor with the lights off and calling the result wearable.
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Fashion and style are meant to be beautiful and individual. They are meant to be expressive yet artistic; something that is pleasant to the eye and communicates to observers. Street style just doesn't do that. It's not avant garde, it's just...atrocious. It is weird and ugly for the sake of being weird and ugly.