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Two Easy Ways To Create A Vintage Inspired Updo

Hello again! It’s Jenny from back with not one, but TWO stunning ways to wear your hair with a chic headband. Just in time for holiday party season, these two looks are sure to turn some heads. Both looks are ideal for mid-length hair and you should start with dry hair that is clean or dirty.

Look #1 – Rolled Pony With a Headband 

rolled ponytail with a headband vintage updo hair tutorial

1. Begin by sectioning your hair into 1-2 inch sections, starting from the nape of your neck. Spray a medium hold hairspray and curl each section with a 1-inch curling iron, working up your head. Its important to curl your hair all in the same direction. It doesn’t matter which direction, just all the same direction is key.

2. Grab your headband or head wrap of choice and gently place in your hair. The key is to stretch it over your head with your hands and get it into your desired place before releasing your hands.

3. Take a comb and back comb the ends of your hair for slight texture.

4. Gently pull back your hair with both hands into a very low ponytail.

5. Secure your low ponytail (a few inches above your ends) with an elastic band.

6. Take your hair where you secured with the elastic and roll it in, going upwards towards your headband.

7. Tuck your roll underneath the headband, fan out your hair and secure with bobby pins.

8. Finish this fab look off with a medium hold hair spray.

Look #2 – The Roaring Twenties Updo 

roaring twenties vintage updo hair tutorial

1. Take 1-2 inch sections and curl them in the same direction throughout the whole head. Use a medium hold hair spray before curling each section for hold.

2. Softly comb your hair out. Try to avoid brushing it too much as the curls will start to drop.

3. Take a headband and stretch the elastic up and over your hair with your hands, and gently release it in the desired spot.

4. Take a comb and a 2 inch section of hair.

5. Use the comb to back comb the section, going upwards. You want to back comb parallell to the ends of your hair and aggressively push it up.

6. Repeat the back combing techinique throughout all of your hair, repeating from the sides to the back.

7. Push up your sections with your comb and spray with a medium hold hair spray.

8. Finish this look off with a firm hold hair spray.

Which one of these vintage-inspired holiday party styles will you try first? For even more hair and beauty inspiration, visit me at