How To Dress Like A Hipster

New to the city and you want to know how to dress like a hipster? It’s not hard, but it does take a bit of finesse to get it right. You'll need to develop a style that is stylish, yet offhand. Hipster style goes all the way back to the leather jacket, T – shirt and jeans look of James Dean, and  continues through the metrosexual looks of international stars like footballer David Beckham. Read our guide and you’ll know how to dress like a hipster in no time.

What you’ll need:

  • Access to used clothing shops
  • A stylish yet ironic attitude
  1. Ironic tees. To dress like a hipster ironic T -shirts are de rigeur, whether you're wearing an "Ames Summerfest" t-shirt circa 1985 or a current design, you'll know you've got hipster style. You'll have to do some searching to find a shirt with the right kind of irony, but collecting ironic tees, you will have a good portion of your wardrobe figured out.
  2. Hoodie.  Every hipster needs a hoodie, and if you want to dress like a hipster, get a hoodie that is either a little too small or a little too large. Light fabrics, like a jersey hoodie, take the cake. Everyone that knows how to dress like a hipster has a good dozen hoodies in an array of colors.
  3. A Beard.  While it's not clothing, it's an important part of your look. Grow some scruff if you want to dress like a hipster. What did singer Ke$ha say at the end of her song, "Your Love is My Drug"? She says, "I like your beard." That dude is a hipster, no doubt. Wear your beard with pride, and grow it thick like that dude Zach Galifianakis.
  4. Worn out jeans or ancient polyester pant. They're not worn out; they are worn in. Moreover, if they hug your hips awkwardly, that's way better for showing you know how to dress like a hipster.  When you are a dude looking to dress like a hipster, you have two general regions of your body to cover, yout top and your bottom.  Putting together the right top and bottom is the most important part of your hipster look.  Make sure you try on your pants and check your outfits out in a mirror before going out.  You can go very wrong when pairing polyester pants with an ironic vintage tee, so choose wisely.  You can certainly invest in many options, but make sure you consider the fact that the pants probably will not flatter you and you are making more of a statement than actually trying to look good.
  5. Fabric belt. Because a buckle is just too buckled down, a grab-and-go cloth belt says casual, beach, and stylish all in one. For even more street cred, pick one up at your local army surplus store.
  6. Gumshoes without socks, retro shoes or flip-flops. There are many brands that meet the hipster expectation. Walk down the street and you'll see some on the feet of people that know how to dress like a hipster. Alternately, if it has recently snowed and you want to show you’re too cool for the weather, wear your flip-flops and walk a mile to your writing workshop. If all else fails, check out your local used clothing shops and get the oldest and most stylish shoes you can find.
  7. Retro to the metro. To be a true hipster, you've got to live in a city with a good metro system. Nothing is better than hopping on "the EL", "the subway" or "the Max", and absolutely nothing is better than doing it in something you purchased at your favorite retro shop.
  8. Messenger bag. Every hipster needs a messenger bag. Get a big one and keep a leather bound notebook in it for your sketches, ideas and poems.
  9. Fixie bike. When you need to get around and the metro isn't running, how are you going to get around? Certainly not on your old ten speed. A fixie bike is much more hip, and it will match your style if you're ready to dress like a hipster.
  10. Wear your favorite microbrew as your Friday night cologne, or go for a blue ribbon winner. Nothing says "In the know” like microbrews or everyone's favorite working man's beer. It's the perfect scent to round out your hipster style.
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