Hipster (Dorothy) Halloween How-To

This post is part of the “Blogging from A-Z April Challenge”! The “H” themed inspiration for today is “hipster.” Enjoy!

Yes, I know it’s April. But it’s never to early to plan your Halloween costume! That being said, it’s possible you’ll run into a suitable situation for playing dress-up before Halloween, anyways. Like Mondays. Or Tuesdays. Wednesdays are good days for dressing up…you get the idea.

This was costume creation last year. After all, the only thing better than Dorothy Gale of Kansas, is Dorothy Gale of Hipster Pretentiousness!

(If you’re confused, there are a bunch of “hipster” definitions on urbandictionary.com, but you’d probably do better by just google image searching: “hipster”, or going to some obscure coffee shop in Brooklyn.)

Feel free to follow this as loosely as you like, or add any other details I didn’t think of!

You can put the outfit together however you want, but I used:

Red shoes
Gingham dress
White knee socks
Fake thick, black rimmed glasses

You’ll also need:

A backpack or bag to carry “Toto” in
“Toto”- I used a stuffed animal cat (with a felt moustache pinned on), because being a dog is overrated
Cardboard sign to hang off of your backpack that reads: “Emerald City or bust”
Pins to put onto your dress (or backpack, etc.)


Every good hipster needs a good set of pins! I made Dorothy’s on Photoshop and they’re available here for you to print to use yourself. I just printed and cut them out, traced their shape onto cardboard, glued them onto the cardboard, and glue-gunned safety pins onto the back of the cardboard so that I could pin them onto the costume.

You may have to size the pins yourself before you print them so that they come out the size you want.

Put your costume together and have fun pretending you’re the hippest ster in Oz.


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8 thoughts on “Hipster (Dorothy) Halloween How-To

  1. Love the post, and there’s nothing wrong with thinking about Halloween in April. I belong to a group of campers who like to do things differently – we had our summer beach party at the end of last October, our Halloween meet was last month and our Christmas pary will be in June!

  2. Pingback: Cool Find: Infant Tattoo Sleeves | Halloween Culture

  3. Pingback: Mew, Mew, it’s The A-Z Challenge, in Review! | ...So Help Me Cats

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