Dress Like Unhappy Hipsters

By: Dylan Marks

Break Studios Contributing Writer

So, you and your buddies have mastered the art of drinking cheap beer while listening to sad indie music, but you haven’t yet learned the secret of how to dress like unhappy hipsters. You’re in luck. Hipster style is far from dead, and it’s not as hard to pick up as you might think.

Things You’ll Need:

  • Skinny blue jeans
  • Plaid buttown-down shirts
  • Vintage t-shirts
  • Glasses
  • Hat
  • Original belt
  • Canvas shoes
  1. Pick up new frames for your glasses. Choose a pair made of blocky black plastic. If you wear glasses, have the optometrist put your prescription lenses in the new frames. If you don’t normally wear glasses, start to do so. Clear, non-prescription lenses were invented so that you could dress like an unhappy hipster.
  2. Find the perfect pair of jeans. While blue jeans are a key element of every man’s wardrobe, hipster style requires attention to detail. Mothball your low-rise bootleg jeans and purchase a pair of skinny jeans. Dress yourself in a form-fitting pair that you can tight-roll for that peg-legged look hipsters love.
  3. Buy shirts at the thrift store. Look for plaid button-down shirts with a little extra structure. Epaulets and scalloped breast pockets both make for an excellent selection. Shoot for a shirt that’s just a touch too small. The same rule goes for t-shirts. Choose t-shirts with names of forgotten cartoon characters or pop icons. Build a collection of vintage t-shirts, so that you have one for every occasion.
  4. Dig out the canvas sneakers. Choose a pair reminiscent of the basketball shoes of the fifties. Boat shoes also present an agreeable option. Pick loud patterns or colors to help you stand out from your hipster compatriots.
  5. Build your blazer collection. Throw on the blazer over the t-shirt and jeans ensemble for a night on the town. This technique is one of the advantages of your newfound hipster lifestyle: The difference between casual daywear and ready to rock involves the addition of a single clothing element.
  6. Accessorize. Pick a belt with beer caps riveted to it, or a checkerboard pattern. Ideally the belt will have a removable buckle, so that you can change your belt buckle depending on your mood. Hats are of the utmost importance to hipsters. Pick a ball cap that screams working class. Alternately, wear a hat from a bygone era to demonstrate your knowledge of history. Hats in this category include fedoras and porkpies. Avoid top hats at all cost. The final key accessories are sweatbands. You need at least two, one for your arm and one for your forehead. In short sleeves, always wear both. When you’re wearing your blazer, drop the armband, but the headband is a keeper.

Tips

  • Look for individual items that will allow you to stand out. Find something that no one else is wearing. You might create the next critical item to be included in every hipster’s wardrobe.
Posted on: Mar. 15, 2011