Easy Updo for Medium/Shoulder Length Hair

Messy Updo

I am NOT a hair person. I’ve struggled with my curly locks since.. since.. pretty much forever. It took me a long time to do a sock bun, and I still haven’t mastered that art form just yet, so updos are generally beyond me.

My friend was throwing a Roaring 20s/Gatsby themed party, and of course the makeup part I had no concerns about, but my hair.. what to do? I’ve seen those pins on Pinterest of the headband over the forehead with the hair tucked up around the headband, but I tried it, and it was very uncomfortable (all my headbands were too tight!) and the hair just wouldn’t stay tucked. I decided to just pin in back with a series of twists and curls, messy but in a way that looks intentional. Normally, I would never post a hair tutorial, but this worked so well, I figure if I can do it, so can you!

You can see from the picture above that I have some bobby pins showing. I know that if you work them in just right and mess around with the curls, you could probably cover it all, but you know that takes like.. effort.. and finesse. Look for bobby pins that match your hair color. Goody makes bobby pins in blonde, brown and black.

Messy Updo for Medium Length Hair

I think I did a pretty good job replicating it- what do you think?

Watch the video below for step-by-step instructions!

What You Need

  • Flat iron if your hair is curly (for straightening the roots) or a curling wand/iron if you hair is straight (to add curl to the ends)
  • Dry Shampoo (optional, for added texture), I used Dove Volume Dry Shampoo
  • Bobby pins
  • Hairpspray (I recommend a light hold so you can build it up), I used Aussie Mega Hairspray Flexible Hold
  • Headband (optional)

1920 Flapper Hair and Makeup

Click here to see how I did my makeup!

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  • Reply Carol Reddick

    What a great way to get easy elegance! Very pretty.

    May 10, 2014 at 11:34 am
  • Reply McKenzie

    Love this! Looks great for the theme, and I love easy updos! Thank you for sharing.

    January 13, 2017 at 2:25 pm
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