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How to Dress like a Hipster

Geek chic combined with retro irony, a hipster's outfit is the definition of "calculated cool." Here's how to get the look.


  • Step 1: Start at the top Sport a worn-in button-down shirt. Avoid boxy, formal fits -- opt for slim cuts and lightweight fabrics instead. Remember, you're trying to dress like a hipster -- not Donald Trump.
  • TIP: Wear a cardigan or blazer -- the more it looks like you hijacked it from your grandparents' closet, the better.
  • Step 2: Rock a fitted T-shirt Rock a plain, fitted T-shirt or find one with a retro logo or design -- movies, TV shows, bands, and video games are all hipster-worthy.
  • TIP: Stick with references you actually know -- there's nothing worse than a fellow hipster calling you out on being a poseur.
  • Step 3: Skinny-fits are a must If you want to dress like a hipster, adhere to the 2-word hipster pants principle: "Skinny. Fit." For added flare, go with acid washes and day-glow neon colors that'll make the other hipsters don their Ray-Bans in awe.
  • TIP: Men, if you're truly brave of heart (and groin) try squeezing into a pair of male jeggings, aka majeggings.
  • Step 4: Get your kicks Slip into hipster kicks like throwback sneakers, deck shoes, or chukka boots. Ladies, if elevation is a must, choose wedges, ankle boots, or schoolmarm kitten heels -- stilettos are about as hipster as non-reusable shopping bags.
  • Step 5: Accessorize Dress like a hipster with the right accessories: knit caps, suspenders, vintage jewelry, messenger bags, and non-prescription "Buddy Holly" glasses are all fine choices. Now, strut the streets and make all those non-hipsters wish they were half as cool as you.
  • FACT: The word "hipster" was used in the 1940s as an equivalent term to "hepcat" -- meaning a stylish or fashionable person.

You Will Need

  • Worn-in shirts
  • Fitted tees
  • Skinny jeans and pants
  • Shoes
  • Accessories
  • Cardigan or blazer (optional)
  • Male jeggings (optional)

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