How to Dress Hipster for Men

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Buried deep in the outskirts of big cities like San Francisco, Portland, Allston or Williamsburg, subsist the hipsters, trustafarians and young creatives of today’s contemporary times. These beings talk the talk and walk the walk -- which is a walk and a talk all its own. And while hipsters are certainly easy to spot on the street, dressing the part may take a couple of tries before you discover it to be an innate talent.

Dress in Vintage

If there are any brand-name items of clothing presently hanging in your closet, get rid of them right now. A true hipster strays from all that is “mainstream.” So, take the road less traveled and hit up some of your local thrift shops. Skinny jeans and ironic or v-neck t-shirts are a few wardrobe staples for hipsters. And don't forget a vintage piece like a leather jacket. Style it with a plaid shirt over a t-shirt and pair with skinny jeans, a beanie and chukka boots for a perfect casual hipster look.

Wear Wayfarer Glasses

Whether or not your eyesight is truly failing, your hipster look is not complete without a pair of groovy wayfarer glasses. The thicker the frames, the better. Pick out a style that is not only bold, but also one of a kind. Black rims are a universal classic -- but you can also try something on in a salmon or iris hue. If you want to be more unique, wear a pair of retro or vintage-inspired men's glasses -- go with huge 70s rims or look down your ironic nose through a pair of coke-bottle specs.

Kick it with Comfy Kicks

When it comes to dressing like a hipster, shoes are just as important as your overall ensemble. To play it safe -- and retro -- invest in a used pair or two of Converse that are at least 15 years old. But there are other options, in case Chucks don’t strike your fancy -- look for a pair of classic Reeboks or Doc Martens. Other options are Vans, chukka boots and Adidas Originals. The key is that your kicks must look worn out. Remember that you are trying to be unique not emo, so have several pairs of shoes to style your look.


Accessorize, accessorize and… accessorize. Add a chunky, knitted scarf to your outfit or throw on a colorful beanie for some unwarranted spunk. Bags are big -- select something with a cross strap like a messenger bag, or something with a lot of little compartments inside. Don’t be afraid to experiment with your trimmings. You can also personalize your outfit with a nostalgic accessory. Any piece that reminds you of your childhood should be in your closet. For example, a Transformers lunch box. If it's vintage, it meets the cut.