Vegan Makeup: Vintage Pin Up Hair and Beauty Tutorial

January 22, 2015

Natural Beauty: Pin Up Ponytail Tutorial

If I could go back in time to the 1940’s and 50’s, I would most certainly become a pin up girl.  These vintage beauties have been style icons for decades, and they show no sign of losing their popularity within our fashion world.  Whether you choose to evoke the full-blown pin-up style daily, or you just prefer to add in a sassy vintage element to your daily look, the stellar style of these bombshells can be yours!

Pin Up girls are well-known for their unique, edgy hairstyles (hello, victory rolls!).  By incorporating elements of their classic hairstyles, you,too, can evoke some serious vintage glamour.  Follow these simple steps to achieve the perfect pin-up ponytail, and you’ll be on your way to becoming a modern pin-up bombshell!

What You’ll Need:

A brush (or comb, depending on what you prefer to use on your hair!)

A teasing comb

bobby pins that match your hair color

a hair tie


curling iron (optional): I generally do not heat style my hair, but you can curl the ends of your ponytail to add a little sass to your look!

heat protectant spray (optional): If you plan on your curling the ends of your hair, applying heat protectant prior to doing so is a MUST.

 The Steps:

1. Create a side part in your hair–choose whichever side is most flattering on you!

2. Divide the front half of your hair into 3 separate sections: one section on each side of your part and a smaller “bang” section.  The “bang” section should be taken from the side of your part that has a larger amount of hair.  If you have bangs that are too short to be styled, skip creating the third section of hair.  The remaining hair will be used to create your ponytail.  Be sure to create sections that leave you with enough hair to create a voluminous ponytail!  Create a style that will be the most flattering for you and your hair type and length.

3. Take the section of hair that you did not create the smaller section in, and using the teasing comb, tease this section of your hair.  Teasing your hair means that you are backcombing it a.k.a. combing your hair back towards your scalp rather than away from it as your normally would in order to create a more voluminous look and a solid base for your victory rolls.  Hold this section of your hair straight up and at an angle and tease the inside of the hair so that the outer portion of your hair remains smooth.  In order to tease your hair successfully, make sure you are holding your hair firmly and backcombing with a fair amount of tension in your hand.  The more you backcomb your hair, the more volume you will create.  For this particular style, you only need a moderate level of volume (unless you would like to create more dramatic victory rolls, then feel free to tease away!).  As you comb your hair downwards towards your scalp, you cause your hair to become knotted into what is often referred to as a “rat.”  If you have very fine hair, try this style when your hair is dirty rather than squeaky clean and use hairspray to give your hair some staying power.  The more textured your hair, the more likely it is to tease well and hold the backcombing.

4. Once you have created the “rat,” you are going to roll your hair into your first victory roll.  Victory rolls can be a little tricky at first, but don’t fear!  You will be a pro in no time.  In order to create your victory roll, pull your teased section of hair straight up and away from your head at an angle and carefully wrap the section of hair around your index and middle finger.  Roll the hair around your two fingers once and then gently remove your two fingers from the section.  Place a finger on each end of the section and continue rolling it downwards and at an angle towards your head.  The preliminary teasing you did will make this step easier because it roughens up your hair a little and makes it less likely to slip out of the roll.  Continue rolling towards your head until the roll touches your head.  Secure the victory roll slightly over your ear with a line of pins on the inside of the roll.  Your style should look something like this at this point:pin-up_ponytail_hair_tutorial_half-finished_style-700x1092
5. Keeping the roll as one solid unit can be difficult as you roll it downwards, so use the bobby pins to gently the pin the roll and wayward strands back into shape if necessary.

6. After securely pinning your first victory roll, repeat the teasing on the second large section of your hair.  Once you have teased this section of your hair to your desired volume, create another victory roll in the same method as before.  Pin the roll over your ear securely by pinning the hair from within the roll itself, also being sure to pin any wayward strands back into the roll shape.  If you have bangs and did not create the third section of hair, skip to Step 7.

7. Take the remaining small section of your hair and repeat Steps 3 and 4.  I chose to tease this section a little bit less than the others since it was a smaller section of hair, but feel free to create some major volume if you’d like!

8. Now that you have your three (or two!) victory rolls, it is time to create your finished vintage-inspired bombshell look!  Pull the remainder of your hair into a low ponytail  (it should be placed slightly above the bottoms of your ears).

9. Once you have your hair secured into a ponytail, you are going to “flip” your ponytail so that it is twisted inwards.  It is a simple hair styling trick that adds a little more flair to your average ponytail!  In order to “flip” your ponytail, pull your hair into two sections directly above your hair elastic (as pictured).  Your hair will remain in the ponytail, but you will now have a gap between two separate sections of hair above your hair tie that will look something like this:Pin-Up Ponytail Hair Tutorial The gap needs to be large enough to pull the bottom of your ponytail through.  Once you have created this gap, flip the bottom of your ponytail over your hair elastic and through the gap until is completely through and back into place. Pin-Up Ponytail Hair TutorialTry adding a fun bow or clip to add another cute vintage-inspired touch to your look!

pin-up_ponytail_hair_tutorial_3After flipping your ponytail, feel free to curl the ends of your ponytail (after you apply heat protectant, of course!) if you would like.  Otherwise, your pin-up ponytail is complete!

Voila!  Your ponytail has gotten a makeover.

Make-Up & Wardrobe Styling Tips:

If you are going for an entirely vintage look, make sure your make-up and outfit match the vintage vibe of your new hairstyle!

1. Cat-Eye eye liner is a staple for any pin-up look.  To create the perfect cat-eye look, use an angled eyeliner brush and a gel eye liner (my current favorite is Pacifica’s Smolder Eye Lining Gel in Tahitian Pearl) and apply your eyeliner from the inner corner of your eye to the outer corner of your eye.  Then, with your eyes open, take a freshly sharpened eye liner pencil (Obsessive Compulsive Cosmetics Colour Pencils work well for cat-eyes!) and flick the end of your eye liner into a sharp point.  The sharper your eye liner pencil, the more defined and precise your point will be.

2. Peachy blush completes any vintage beauty look!  Try Obsessive Compulsive Cosmetics Creme Colour Concentrate in Grandma or Etherealle’s Matte Mineral Blush in Blissful (for a peachy pink) or Sweet Ginger (for a more true peach shade).

3. A deep red or vivid coral lip adds the perfect finishing touch to your glamorous pin-up look!  Try Obsessive Compulsive Cosmetics Creme Colour Concentrate in Grandma for a beautiful coral shade or try the combination of their Lip Tars in NSFW and Anita for a show-stopping red!  Insomnia Cosmetics lipstick in Witch Hunt will also give your lips a brilliant blood red color.

4. Don’t forget about your brows!  Properly groomed eyebrows are a must for the proper pin-up look.  Fill in sparse brows with an eye liner pencil and angled eye liner brush or using an angled brush, brow powder and a clear eye liner pencil to seal in the color and keep wayward hairs in place!  Addictive Cosmetics (available on Etsy) sells a 100% natural, vegan, and cruelty-free brow filler in flattering shades for all hair colors!  Don’t overdo it when filling in your brows–the more natural they look, the better!

5. Peplum tops, skirts, and dresses give you a vintage pin-up vibe while still being figure flattering!  I find peplum dresses to be incredibly flattering; they accentuate your waist and hips in the most flattering way possible.  A peplum helps create the classic pin-up silhouette without clinging to your body; they fall away from the body, thus hiding a few problem areas you might be uncomfortable with.

6. High-waisted pants and pencil skirts are also great ways to incorporate a bit of the pin-up style into your everyday wardrobe.  Pair them with a top in a sassy print (leopard print, polka dots, and gingham are seen on a lot of vintage beauties and modern pin-up ladies!), and you’ll be sure to feel like a vintage bombshell!

7. Peep toe shoes (heels in particular!) will not only up your vintage game, but they will also elongate your legs, providing the perfect compliment to your high-waisted pants and skirts!

8. Bows!  Bows are the perfect way to accessorize and add a sweet touch to your pin-up inspired look!  Try adding them to your hair (they can be placed over your hair elastic as seen above!), your jewelry, handbags, and shoes for an added girly, vintage touch.

9. Killer confidence!  The key to rocking any look is having awesome self-confidence.  You are beautiful, inside and out, so don’t be afraid to show that off to the world (along with your new glamorous pin-up style)!Pin-Up Ponytail Hairstyle TutorialVegan Makeup: Vintage Pin Up Hair and Beauty

Hello, vintage beauty!

More vegan makeup and hair tutorials:

Boho Chic Tutorial

Everyday Contouring

Retro Bombshell Tutorial


Photo: Becky Curl

Becky Curl is a freelance wig and make-up artisan based in Chicago and a recent graduate of The Conservatory of Theatre Arts at Webster University in St. Louis. When she’s not working in the theatre, Becky enjoys exploring new vegan and eco-friendly beauty products and watching copious amounts of Saturday Night Live. Check out her portfolio here and follow her on Instagram @becky_curl and Pinterest @beckycurl!


always stay inspired!