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how to dress like a hipster

In advance of my kids’ school auction, I was asked to write a little something for parents about how to dress for the event. The theme of my kids’ auction this year is Portlandia, as in, the TV show.

In any given year, dressing for the school auction is anxiety inducing, because parents at my school, being involved and enthusiastic Montessori parents, actually dress up according to each year’s theme.

That’s a problem for me because I hate costumes. I hated costumes long before married friends of ours suggested that the four of us dress up for Halloween as the gang from Scooby-Doo. “We can be Daphne and Fred,” the wife half of the couple chirped. “Tom can be Shaggy, and you can be Velma, Yoona. It will be so perfect!!” Perfect for whom? Daphne and Fred were hard-bodied and attractive. Tom is tall and white and could conceivably be made to look like Shaggy, but Tom was deeply offended by the suggestion. And me! Velma is the nerd who wears a baggy orange turtleneck sweater and knee socks. Why does the Asian always have to be the nerd? It all seemed so unfair, as if they’d suggested that we dress up as characters from the Lord of the Rings and then suggested that I’d make the perfect Gollum.

But this auction is for my kids. I’ll do anything for my kids, except wear a tankini. Portlandia means hipsters. I could throw something together, but what about Tom, who wears suits five days a week? I had never really thought about the components of a male hipster outfit. I started with online research, and found a Wikihow page called “How to Dress Like a Hipster” that included helpful tips like “Be under 30 years old.” Anyway, here’s my take.

Step 1: glasses


In case it’s not evident from his expression, I had to blackmail Tom into participating in this post. The blackmail went like this. Yoona: “Tom, I’ve fulfilled 12 volunteer hours for the school this year. How many have you fulfilled?” Tom: “I brought the guinea pig home that one weekend and bought the guinea pig supplies.” Yoona: (penetrating stare).

Anyway, hipsters love glasses. The more awkward, the better. I bought these for ten dollars at Lloyd Center and wore them religiously for two weeks until someone at work asked whether they had prescription lenses in them. I would have lied but I was worried that some jerk would snatch them off my face and look in the lenses to discover that not only were they not prescription, they had a cheap film over them that actually inhibited vision. Once people found out my glasses were fake, I got all sorts of unsolicited opinions. One partner was borderline distressed about it. “Why would you wear glasses if you don’t need to wear glasses??” When put that way, I felt sort of dumb about them. But glasses are a solid first step to hipsterville.

Step 2: plaid button down


Every waiter in town wears one of these. Usually they are buttoned up to the neck and tucked into a pair of high-waisted jeans, but Tom refused to do that. Anyway, the tighter the better. I think the one here is three sizes too small.  Straining buttons are great.

Steps 3, 4, and 5: the hoodie, the hat, the ‘stache


I wasn’t present when these photos were taken, as I was out of town. I gave Tom and Cuz my instructions and they did a bang up job, but Tom started getting upset so Cuz made the decision to fast forward from Step 2 and started piling everything on at the same time. The hoodie is de rigueur. The hat is usually of the skull cap variation, but you might go indigenous with a highly patterned number. Anyone who doubts my love for my kids should know that I had to visit the costume place on Hawthorne to procure this moustache, and that place scares the bejeezus out of me. For starters, I hate costumes. Also, it’s really cold in there because it’s staffed by vampires.

The moustache cost me $14.00 and is made out of someone’s real hair. Thinking about that for too long makes me want to vomit, but at least you know it’s authentic.

Step 6: the skinnies


Skinny jeans are a hipster must. We ran into some regional issues with the skinny jeans, as Cuz is from NYC, and apparently in NYC the hipsters only wear skinny black jeans. We tried to buy some from American Apparel for this shoot but NEWS FLASH you can no longer return items for a refund at AA. There goes everyone’s Halloween, I guess.

In Portland you see skinnies in all colors. I am particularly impressed by skinny jeans in raw denim, as they look spectacularly difficult to pull on. These are Tom’s own skinnies but as skinnies go, they aren’t that skinny. Still, every time I ask him to wear them he complains that they hurt when he eats. When you can’t feel your legs or your reproductive organs, just remember that it’s for a good cause. It’s for your kids’ education.

Step 7: put a bird on it


The joke goes that people in Portland like to put birds on things. We didn’t have any birds in the house except some chicken breasts and this Korean wooden duck but you get the idea. You might even get other animals involved. Like so.


So there you have it. How to dress like a hipster in seven easy steps. Any questions? I’ll refer you to Cuz.

Tom can’t wait for this auction.

51 Comments Post a comment
  1. This is my favorite post in a years worth of following and reading blogs. LOVE LOVE LOVE IT. Probably because a) I happen to watch Portlandia and think it’s amazing and b) I grew up in the most liberal hippee hipster town called Oberlin in Cleveland, Ohio.. the town breathes and breeds hipsters. HAHAHA. great post as always! Much love!

    March 15, 2013
    • ha that’s awesome. i can’t believe you watch portlandia. i can’t believe anyone outside of portland watches portlandia

      March 20, 2013
  2. This is HILARIOUS!!! I absolutely love it, especially the stuffed animal audience.

    February 25, 2013
    • first time those stuffed animals have seen any action

      February 28, 2013
  3. Coming from another hipster haven (Austin) I was going to leave commenting to those of you chronologically eligible types for hipsterhood but I caved and simply must suggest one tiny tweak.

    Overall you nailed it but, everybody? Scour all available closets for Tom’s slip-on shoes (not your amazingly game husband Tom’s personally owned foot wear, but rather that brand of cloth shoes that break the EarnestoMeter simply by existing).

    I’m not sure any guy can ever look hipster “enough” without also looking like he raided his grandmother’s closet for her old espadrilles….

    Request for your next fashion post? How to dress Rockabilly….

    February 23, 2013
    • I love all the regional variations! Espadrilles would never work in sodden Portland, but I love the idea of it

      February 26, 2013
  4. This is hilarious! Ironically I came across this post right after my co-worker sent me a link to the “30 Most Portland Things That Have Ever Happened in Portland…” it’s pretty funny if you have time to take a look. 🙂

    February 22, 2013
    • so funny. “a robber who looked like a hipster.” god i love this town

      February 28, 2013
  5. Emily Jones #

    That was awesome. Hipsters probably don’t say awesome. Now how many volunteer hours do you get for writing that blog? And when will you publish one for the women?

    February 21, 2013
  6. You may not be able to out do Tom this year with your costume, he looked like a natural – too funny!

    February 21, 2013
  7. Oh my goodness! Reading this post totally made my morning! I recently had a hipster themed birthday party and let me tell you, this post would have been fabulous to forward around to my nearest and dearest when they were trying to figure out what to wear.

    February 21, 2013
    • that’s an awesome party idea. except for the costumes of course

      February 21, 2013
  8. Love it as always! Took me all day to finally read it… But in true Yoona fashion it was worth the wait! Thanks for writing I love your blog!

    February 20, 2013
    • I find I’m more easily amused in the evening, so perhaps it’s best you waited

      February 21, 2013
  9. Nailed it!

    February 20, 2013
    • it really helped that Tom has skinny legs

      February 20, 2013
      • I imagine that would be a plus. By the way, his Jack Purcells gave me major case of shoe envy.

        February 20, 2013
      • yes i love those–i own the same pair. john varvatos

        February 20, 2013
  10. The mustache kills me. My father had one like that in the 80s.

    February 20, 2013
    • I’d want one that shape if I had to have one

      February 20, 2013
  11. I retched a little hearing that the stache was actually human hair. But Tom was such a good sport about this and the photos are hipster-making indeed. Loved your write-up. Hope the parents (and the beneficiaries of all this: the kids) really appreciate your efforts.

    February 20, 2013
    • they had a bunch in different colors. i couldn’t tell if it was hair from moustaches or hair from other parts of the body, in which case tom has given more than he knows

      February 20, 2013
  12. Karen #

    What’s so bad about tankinis? I mean, if you can’t pull off the bikini because of the post-baby roll, isn’t it (nominally) better than a one-piece? Especially because it’s WAY easier if you have to pee all the time?

    February 20, 2013
    • it’s an irrational loathing but i hate them. something about a tankini seems like a concession to motherhood and the end of one’s feminine mystique. give me a ruched one-piece any day, or a strapless one piece, or a one piece with a deep V. having said that i know many people wear them and look good in them. this reminds me of a brilliant piece on skorts written by the inimitable paige parker:

      February 20, 2013
      • Oh my gosh, I just stumbled upon your blog, and this is the first post I read. I will be making myself comfortable, if you don’t mind. You had me at “irrational loathing of tankini.”

        February 28, 2013
  13. Bt #

    Legendary. On many levels. Bushy ‘stache–love.

    February 20, 2013
    • brad Tom wants me to ask you if you had a penn state player in your lap the other day

      February 20, 2013
  14. Yoona!!! Hilarious! Hilarity! Amazing! Made my day. Tom is a rock star.

    February 20, 2013
    • thanks for reading. and tom is totally an (aging) rock star

      February 20, 2013
  15. Andy #

    Not wearing a tankini is part of what makes you a good mother. Even if wearing a tankini would save a life. I know, personally, I would rather die than bear witness to my mother in a tankini.

    February 20, 2013
  16. You make me laugh every time I visit your blog! Love it!!!

    February 20, 2013
  17. Shoe #

    This is my favorite Yoonanimous in quite some time. Bravo TRJ, you’re a good man.

    February 20, 2013
    • i should have put him in your pink v-neck. shoot

      February 20, 2013
  18. Cracking up right now. Your husband is BEYOND a good sport. Thanks for the post!

    February 20, 2013
  19. Now i know. Funny post!

    February 20, 2013
    • my friend was talking about how she was trying to describe what a hipster is to a german. and it was very difficult. you know one when you see one, but hard to define

      February 20, 2013
  20. Hilary Wang #

    So glad you wrote this, Yoona! It will help David out a lot. What do hipster moms wear to the auction??

    February 20, 2013
    • i don’t know, hilary! i have not dressed in costume for the auction before but am hopeful i can figure something out. i have cuz to advise me after all

      February 20, 2013
  21. Ryan #

    you two are an awesome couple!

    February 20, 2013
  22. A modest request: Could you blackmail Tom into reprising this for our next hearing? Please?! Pretty please!!!

    February 20, 2013
    • ah david. i fear not. tom’s going to be so psyched that opposing counsel are reading this post

      February 20, 2013

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