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If you take your cue from celebrities or from the masses at the mall, it's time to look elsewhere. Urban hipster style may overlap with mainstream style, but only in the name of being ironic. Capturing this look is about copying urban street looks without appearing as if you are copying them. Your goal is to look more counter-culture than corporate culture, so rummage through your grandparents' attic and thrift stores to find your ensembles.
City cool is about mixing more than matching. Urban hipsters eschew coordinated outfits in favor of single items they can pair with jeans or a hoodie. Anything goes in the name of irony, but certain looks are hipster staples. Worn-in or distressed jeans go anywhere from hanging at the bike shop to drinking a double-something at a street-side cafe. T-shirts from the '70s, '80s and '90s, particularly those featuring some iconic advertising logo or cherished childhood star, can earn you street cred.
We Got the Beat
Retro counterculture informs urban hipster style, but it tends to favor beats or punks over hippies, unless you live in Portland, Oregon. This is why basic black never gets tired for urban hipsters, as it alludes to the uniform worn by beat poets in the East Village and, before them, the philosophers and bohemians of the Left Bank. If you feel the need to bust out of that black cloud, dark gray is an acceptable variation.
By daytime, urban hipsters wear shoes for covering the city by foot, bike or public transportation. Converse high-tops and low-tops remain a favorite choice, easily customized by drawing on the canvas with a permanent marker. At night, the look is decidedly retro with pointy-toed boots, mod platforms or slingbacks in bright hues. Used, worn-in, vintage and thrift shoes mix better at that basement party than shiny new kicks.
Urban hipster style is timeless in that it loves all the eras, but it can also be fickle. The used Hush Puppies that were huge a decade ago are now stuck far back in closets from Williamsburg to Seattle. To stay current with the urban hipster, you need a crystal ball, because it takes a lot of effort to look this effortless. Today's thick, black-framed glasses may be tomorrow's acid-washed jeans. Look to the streets in city neighborhoods, particularly those with high concentrations of college students, artists and independent cafes, for the latest in hipster fashion.