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Iconic Hipster Costume Ideas: Dressing Up as Your Favorite Hipster Celebrities & Characters

When it comes to dressing up for Halloween or a costume party, hipster culture offers a treasure trove of inspiration.

Hipsters have a knack for creating unique and iconic looks that draw from various subcultures and eras. If you’re looking to stand out and pay homage to your favorite hipster celebrities, I’ve got you covered with some iconic costume ideas.

One of my very first adult hipster parties was back when I was in college in the oughts and I dressed as Pete Doherty from The Libertines. My friend at the time dressed as Amy Winehouse. We thought we were so cool!

I know Gen Z is the “it” culture at the moment— they are the moment! But that doesn’t mean hipsters are completely out of style yet. In fact, I have a feeling there might be a small resurgence of hispter culture from the ’90s and early ‘oughts when hipsters were still (kind of) cool.

From musicians to actors and artists, here’s how to capture the essence of these famous hipster figures for Halloween. Personally, I think these make great gay costume ideas because they’re not as stereotypical, they’re still fun, and they’ll be comfortable for what would most likely become a rager Halloween party.

11 Iconic Hipster Costume Ideas for Halloween

1. Bob Dylan

The Look: Bob Dylan, the folk-rock legend, is a true icon of original hipster fashion. Think tousled hair, a harmonica necklace, vintage denim, and a pair of round sunglasses. Don’t forget an acoustic guitar to round-off the very heterosexual look!

How to Achieve the Look:

  • Find a pair of round, wire-framed sunglasses.
  • Wear a messy wig or style your hair in Bob Dylan’s signature tousled fashion.
  • Layer up with a denim jacket, a graphic t-shirt, and jeans.
  • Accessorize with a harmonica necklace and a guitar (real or prop).

2. Zooey Deschanel

The Look: Known for her quirky and vintage-inspired style, Zooey Deschanel’s look is all about whimsical dresses, bangs, and a pair of retro glasses. She’s the queen of the hipsters from my generation.

How to Achieve the Look:

  • Get a wig with bangs or style your hair with fake bangs.
  • Opt for a retro-inspired, knee-length dress with a floral or polka dot pattern.
  • Wear opaque tights and Mary Jane shoes.
  • Accessorize with a vintage-inspired handbag and a pair of oversized glasses.

3. Wes Anderson Characters (e.g., Margot Tenenbaum)

The Look: Wes Anderson’s films are a goldmine for hipster costume ideas. Margot Tenenbaum from “The Royal Tenenbaums” is a prime example with her fur coat, red barrette, and heavy eyeliner. You could get all sorts of creative with other characters from other Wes Anderson movies.

How to Achieve the Look:

  • Find a faux fur coat or a vintage-style fur stole.
  • Style your hair with a red barrette or clip.
  • Apply dark, dramatic eyeliner and mascara.
  • Wear a striped or polo dress with a wide belt.
  • Carry around a wooden finger, as Margot is known for her distinctive prop.

4. Kurt Cobain

The Look: The grunge icon Kurt Cobain’s look is a perfect choice for those who prefer a more rebellious hipster vibe. Think flannel shirts, ripped jeans, and a disheveled blonde wig.

How to Achieve the Look:

  • Wear a tousled blonde wig or style your hair with a messy, unkempt appearance.
  • Don a plaid flannel shirt and let it hang loosely over a graphic t-shirt.
  • Pair with ripped jeans and combat boots.
  • Accessorize with a fake cigarette and a guitar, channeling Cobain’s rock-star aura.

5. Andy Warhol

The Look: The iconic artist and pop culture icon, Andy Warhol, had a distinctive style. Embrace his avant-garde look with a white wig, black turtleneck, and oversized glasses.

How to Achieve the Look:

  • Find a white wig with his signature haircut.
  • Wear a black turtleneck sweater, maybe some black jewelry.
  • Accessorize with a pair of round, oversized glasses.
  • Carry around a fake can of Campbell’s soup as a playful nod to his famous artwork.

6. Lana Del Rey

The Look: Lana Del Rey’s vintage glam style is instantly recognizable. Think retro dresses, flower crowns, and her trademark winged eyeliner. She’s one of my all-time favorite musicians, and with her Waffle House look from earlier in 2023, there are all sorts of great costume ideas to capture the Lana look.

How to Achieve the Look:

  • Style your hair in loose waves or curls.
  • Wear a vintage-style, knee-length dress with a cinched waist.
  • Accessorize with a flower crown.
  • Apply winged eyeliner and bold red lipstick for that Lana Del Rey allure.

7. Pete Doherty

The Look: The Libertines frontman Pete Doherty epitomizes the indie rock hipster aesthetic with his disheveled style. Think disheveled hair, a leather jacket, band merch, and a drunk or high attitude.

How to Achieve the Look:

  • Mess up your hair for that signature bedhead look.
  • Don a leather jacket with a vintage band t-shirt underneath.
  • Add some skinny jeans and worn-out sneakers.
  • Accessorize with a guitar pick necklace and wristbands.

8. Time Traveling Hipster

The Look: This creative and humorous costume idea involves mixing and matching different eras and styles to create a time-traveling hipster. Think a top hat from the 1800s, a disco jumpsuit from the ’70s, and futuristic sunglasses.

How to Achieve the Look:

  • Combine clothing and accessories from various decades.
  • Be eclectic and mismatched, as if you’ve traveled through time collecting fashion souvenirs.
  • Accessorize with quirky items like a pocket watch or a space-age gadget.

9. Grandma as a Hipster

The Look: Embrace the trend of “grandma chic” by dressing as a modern hipster with a grandma twist. Think floral dresses, oversized cardigans, and cat-eye glasses.

How to Achieve the Look:

  • Wear a vintage-style floral dress or a patterned skirt.
  • Layer with a chunky cardigan or shawl.
  • Add cat-eye glasses and a string of pearls for a touch of grandma flair.
  • Carry a knitting needle or a crochet hook as a playful prop.

10. Brooklyn Hipster

The Look: Capture the essence of a Brooklyn hipster with a focus on local and sustainable fashion. Think organic cotton clothing, a canvas tote bag, and a love for artisanal coffee. This is admittedly a very basic look, because despite the rumblings of the hipster trend being over, in Brooklyn, there’s still very much a hipster vibe.

Today, though, the Brooklyn hipster is much more than what it was when Williamsburg was cool. It’s now a Bushwick hipster—think ketamine and a penchant for non-monogamy.

How to Achieve the Look:

  • Choose eco-friendly clothing made from organic materials.
  • Carry a canvas tote bag with a local farmers’ market logo.
  • Accessorize with a reusable water bottle and a love for handmade, artisanal products.

11. Portland Hipster

The Look: Portland hipsters are known for their love of the outdoors and all things eco-conscious. Think flannel shirts, hiking boots, and a reusable coffee cup.

How to Achieve the Look:

  • Wear a plaid flannel shirt with rolled-up sleeves.
  • Opt for jeans or cargo pants.
  • Sport hiking boots or trail shoes.
  • Carry a reusable coffee cup and a tote bag with a nature-themed design.

Whether you’re a fan of folk music, indie films, art, or just the eclectic world of hipster culture, these iconic hipster characters and creative costume ideas are sure to make you the life of the party at your next costume event. Get creative, mix and match elements, and most importantly, have fun embracing the unique spirit of these hipster icons.