Portland-Inspired Pop Culture Halloween Costumes for 2021

For the procrastinators among us, here's everything you'll need for last-minute costumes that will get you nods of recognition in the Rose City.

By Cami Hughes October 26, 2021

Halloween is less than a week away, and it's past time to get the last pieces of your costume pulled together. Still struggling to find an iconic costume? Grab inspiration from the world around you, specifically from our keeping-it-super-weird city.

Here are six Portland-inspired costumes to get your gears turning.


Ted Wheeler prior to being tear-gassed. 

Portland Mayor Ted Wheeler (With Optional Tear-Gas)

Back in July 2020, Mayor Ted Wheeler came out to meet with protesters, and wound up with a faceful of tear-gas. Turn this low moment for our mayor into a couple’s costume with your partner dressed as a tear-gas canister. 


  • Light blue surgical mask
  • Silver hairspray
  • Clear safety goggles
  • Black zip-up jacket with no hood

Tear-Gas Canister:

  • Silver clothes
  • Silver hairspray
  • Dry shampoo aerosol can (spray gives off a light white smoke vibe) 


Unipiper dressed as Darth Vader playing his famous flaming bagpipes while riding his unicycle in Vancouver, BC's St. Patrick's Day Parade. 

Image: Sarah Kidd

The Unipiper

The Unipiper is one very specific embodiment of the Portland sensibility—talent, one-of-a-kind showmanship, and a whole lot of weirdness. Since finding a unicycle in a Dumpster on his college campus, Brian Kidd has gained over 130,000 Facebook followers and 11,000,000 views on YouTube. 

What you need to complete the look:

  • Unicycle (unicycling skills are a bonus)
  • Kilt
  • Black combat boots
  • Darth Vader mask
  • Black cape
  • Bagpipes (flames not included, nor advised)


Travis Boersma ringing the New York Stock Exchange.

Travis Boersma at the New York Stock Exchange

Oregon-born company Dutch Bros Coffee went public on the New York Stock Exchange this year, and company cofounder Travis Boersma got to ring the opening bell. As one does, he wore a “Rage Against the Machine” shirt while at the literal center of American capitalism.

What you need to complete the look:

  • Rage Against the Machine tee
  • Square sunglasses
  • Black baseball cap, worn backward
  • Wooden hammer or mallet
  • Cup of Dutch Bros coffee 
  • Dollar bills teeming from your pockets


Aidy Bryant as Annie in season 3 of Shrill.

Annie Easton in Shrill

Shrill takes place in Portland and follows Easton, a journalist played by Aidy Bryant, working to prove her worth in a society that knocks her down for the size of her body. There are many options besides the ones suggested below, so go crazy!

What you need to complete the look:

  • Strapless red dress
  • Magenta handbag
  • Bright pink chunky heels
  • Moxie and a stash of killer one-liners

Big Pink standing over Portland. 

Image: Steve Morgan 

Big Pink

One of Pietro Belluschi’s iconic Portland creations is a 42-story pink skyscraper that sits over West Burnside Street. You've probably seen it before, but did you know, it’s the largest office building in Portland in terms of space, but only second in height.  

What you need to complete the look:

  • A rectangular box—hopefully the recycling is not already out
  • Metallic pink spray paint
  • Black Sharpie
  • Pink ribbon
  • Height would be a bonus

How to put it all together:

Spray-paint the box in the metallic pink paint, and then draw out the cascading thick lines found on the side of the building. Once all paint is dried, attach pink ribbons as shoulder straps, and go on to strut your stuff.

Ramona Quimby, through the years.

Ramona Quimby and Henry Huggins

Celebrate the life of beloved McMinnville-born author Beverly Clearly, who died in March this year, by dressing up as one of her iconic characters, the indefatigable Ramona Quimby. Take inspiration from the original cover art of the books, or modernize your look with the updated versions. Here’s a guide to dress up like the original cover art.

What you need to complete the Ramona look:

  • Scoop-neck T-shirt (red or white recommended)
  • Jean material or black overalls
  • Homemade paper bunny ears—you can figure these out yourself, surely 
  • More moxie


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