42 Pin-Up Hairstyles That Scream “Retro Chic” (Tutorials Included)

📷 Photos updated on December 6, 2022

Cindy Marcus Hairstylist, Editor-in-Chief

Pin-up hairstyle creates a retro glam look by rolling up a section of the hair paired with sleek, big waves. Smooth upswept rolls, baby bangs, waves, and elegantly coiled locks are the epitome of such a vintage look.

Hallie Kaplan is a stylist from Las Vegas who specializes in retro cuts and styles. According to her, these are what you, ladies, need to remember if you want to pull off this hair idea.

💡 Key Things to Know First

Ask your stylist whether they have experience with vintage cuts and styles, and get advice on replicating the look at home.

The Middy or horseshoe cut is perhaps the most iconic of the classic styles. It works for any woman with any hair type or texture that desires heat-free curls.

Remember, vintage hair only looks great when styled. Without a curl or some movement, it can look a like a mullet or a mushroom.

When styling pin-up hair, start at the bottom to get the perfect set, brush out, or roll.

One common misconception is that brushing will ruin the curls after a set. On the contrary, it’s crucial to keep brushing and sculpting until it’s right.

Kaplan said it takes a lot of patience, practice, and hairspray to create the ideal retro look. Feel free to grab some inspiration from these photos of amazing pin-up hairstyles!

Photos

Instagram @emilyolyvia

#1: Sassy Pin-Up Beehive

A sassy hairdo perfect for any retro themed party! The only things you’ll need to recreate this gorgeous look is lots of hairspray and creativity!

Instagram @elizabeth_grace_makeup

#2: Classic 50s Style

Try a really classic 50s style, the sort you see on advertisements and posters from around that time period.

This is one of those styles that is so simple and classic to recreate, but it looks like you’ve spent a ridiculous amount of time styling the hair.

If possible, start with hair that’s not freshly washed because it will hold the curls better and make the victory roll so much easier to create. When creating the curls, use a heated wand then put them in pin curl clips for about 20 to 30 minutes to let them set. This will help you really get that bouncy curl.

Use a bristle brush to gently soften the curls. If you have hair that is prone to frizz, smooth a small amount pomade through with your fingers. This will keep your curls smooth and shiny, and stop the hair from frizzing when brushing the curls.

Instagram @miss_bombshell_mel

#3: Modern Victory Roll

This look is simply a modern twist on a very classic 1940s victory roll style.

I love this look because of its versatility. It can be worn with jeans and a t-shirt for a rockabilly look, but it’s classy enough to be paired with a dress for day or evening wearability as well.

This is a great look for a beginner or someone with an advanced skill set. The best advice I can give when it comes to creating rolls is, when you think you’ve teased it enough, tease it a little more. I find that most people are afraid to tease their hair. With vintage styling, I find teasing key. I recommend using a texturizing power like Puff.Me at the roots then teasing with a “C”-shaped motion. Lightly brush out the surface and use a pomade or wax to smooth flyaways.

Use caution when placing your pins to hide them and finish with a firm hold hairspray. If you struggle with frizz, this look can still appear very authentic with a more natural shape (and very little product) as opposed to these very smooth rolls. A quick curl of the ends really pulls this look together. You can add a scarf or a flower as well.

Prepare for the compliments! This classic look is sure to turn heads and get people talking. Put on your favorite lipstick you’ll be grinning a lot in this updo hairstyle!

Instagram @andreareeshair

#4: Modern Flapper

Consider doing a modern take on the retro pin-up or flapper style. It is softer than traditional fingerwaves because it was set with a 3/4-inch iron and then formed into the waves. It’s so classic and glamorous!

The waves frame the face and transition back into the chignon. It’s set, but it doesn’t look stiff. It has a softness to it.

To style, you need good heat protection. use Goldwell Style Sign Twist Around spray which is designed specifically for heat setting curls. The density of the hair will determine the size of the wave pattern you can wear, but it works on all types of hair.

There’s something sassy about this look. When you think flapper or pin-up, there’s definitely an attitude associated with it. The outfit has to match this look! I’m not saying you need to wear a flapper dress or a pin-up corset, but this is a classic look and you wouldn’t want to pair it with something too modern.

Instagram @katskreations.yyc

#5: Classic Retro Glam

This retro hairstyle is easy to create and doesn’t take a lot of time to actually style. I consider it to be a classic retro look due to the ease and versatility.

This look can be worn dressed up or dressed down. It’s a classic style for any 50/60s glam fan due to the victory rolls.

This look can be created with a curling iron, but if you have fine hair I highly recommend using rollers for more volume and longevity of the curls. If using a curling iron, definitely clip each curl in a barrel formation after it has been curled to allow each curl to cool completely before you start working with the style.

Using a thermal spray in the hair before you apply any heat will help the style last longer as well as protect the hair from heat damage. I used Joico Iron Clad. Apply the thermal spray immediately before you curl or put rollers in in dry hair. If using rollers, allow hair to completely cool before you take them out.

Once curls are created, use a light hairspray all over. To create your victory rolls, backcomb each section to build a base for the curl to be clipped into. Smooth out any flyalways that are visible. Once finished, spray everything with a shine spray and finishing hairspray. Use Joico Flip Turn Hairspray and Kevin Murphy Shine Spray.

This look can be great for any woman who has medium to longer length hair. Face shape will only affect the size of the victory curls, as smaller faces can get away with slightly bigger ones. For longer faces, I wouldn’t suggest a lot of volume on the top of the head, but more on the sides.

This look takes about an hour from start to finish to create. Once the curls are created, the actual style itself takes about 15-20 minutes.

Instagram @belles.and.brides

#6: Double Victory Roll

The double victory roll is such a classic vintage style. You can change it up to suit who you are and always look like a pin-up goddess. Add more rolls or even take one away, the sky is the limit!

This masterpiece is created by Abigail Pope, a stylist from West Sussex, UK. For women wanting this look, she suggests embracing the backcombing!

“There needs to be a lot of great backcombing, held with strong-hold hairspray. Do this in small sections for the best results, smooth the outside with pomade ,and hide those bobby pins. This means that even girls with thin hair can get involved,” Pope explains.

You can certainly style a roll using straight hair, but it is so much easier when curled. Pope adds, “I like to curl in the direction of the final roll. Just roll the hair around your fingers and down the hair, then secure. Curl the rest of your hair all in the same direction and either leave the curls loose, or brush them through to create vintage waves.”

You don’t need to be a dedicated vintage starlet or be wearing a swing skirt with a massive petticoat to wear this style. Rock this look with some high wasted jeans, Converse and a matching hair flower and you’ll ooze glamour and pin-up style.

Pop it all in a silk head scarf overnight and with a little smoothing, it will be ready for another day!

Instagram @szrovrcmb

#7: Modern Femme Fatale

A pin-up style with a low ponytail makes a modern take on the victory roll while still maintaining a classic feel with the silhouette.

Look creator Sass Moreno of Costa Mesa, CA used the bobby pins in the ridges down on the scalp to secure the look. She advises, “Make sure to hide them well! Clean sectioning will ensure a neat and polished style.”

Achieve the look by using a teasing brush, sectioning clips, a rattail comb, bobby pins, a 3/4-inch curling iron, S Factor Vivacious Hairspray, and S Factor Flat Iron Spray.

The great thing about the vintage hairstyle is that you can find one that suits each face shape and hair type, though most are easier to create with longer hair. As far as a daily style, these looks can seem a bit labor-intensive, but the more you practice the easier it gets.

Moreno recommends this look for ladies who has a holiday or New Year’s Eve party. It really brings the drama, so dress accordingly my femme fatales!

Instagram @kayejessica

#8: Dry Finger Waves

The dry finger waves carry out a very Old Hollywood/Veronica Lake/1940s style.

Style creator Jessica Kaye of Texas loves how the waves frame around the side of the face. It really brings out the eyes and lips for a very glamorous and alluring look.

“Create a great foundation first,” Kaye recommends. “Use an Aquage Uplifting Mousse, but gel spray at the root can also do the job. Lightly mist the hair with a heat protectant (Aquage Beyond Body) that builds the body and has a medium hold. I also like Sebastian’s Working Spray for this look,” she adds.

To create the curls, use a 1 1/2-inch curling wand from Hot Tools.

Use a detailing cream to smooth out any flyaways, then slowly pull apart the curl without disturbing the curl’s formation. To marry finger wave sections together, lightly put the sections together and tease gently so that you get a finger wave effect.

Long or medium length hair with longer layers looks best with this look. Short hair looks best set with wet finger waves.

All face shapes can wear this look. “Keep in mind that the goal with any haircut or hairstyle is too achieve a more oval-shaped face,” Kaye emphasizes.

This look can also be easily turned into any updo for a wedding or special occasion. The hairstyle is timeless!

Instagram @agadorspartacusss

#9: Hidden Pin Curl Swirl

A vintage-inspired look with a modern twist? Yes, please! Hairstylist Erika Alvarado of Las Vegas, NV created this look with the hidden pin curl swirl at the top of the head.

To recreate this look, use a thermal protectant to prep the hair. Set with pin curl clips and use a 3/4-inch curling iron. In the back, curl the sections going downwards in horizontal sections and part the hair in a deep part.

On the side with the small victory roll, curl the sections going upwards. On the other side with the most volume or hidden pin curl, curl the hair going downwards in sections. After letting the curl set cool for 15 minutes, brush them out and set it with R+Co’s Outerspace Flexible Hairspray.

For the front part of the hair, tease it and mold one side into a small victory roll and pin in place. On the other side, mold two barrel roles going back.

Smooth the front with Suavecita Pomade and finish with R+Co’s Outerspace Flexible Hairspray.

According to Alvarado, “This hairstyle is great for all hair types from fine to thick hair. Mid-length hair is best to recreate this look, but you could always create a similar version with shorter or longer hair.”

This is a hairstyle for any woman who loves to try a style “outside the box” and someone who appreciates classic styles. This is a great look for all ages and for any occasion.

Instagram @lottapincurls

#10: Classic Vintage Set

This look is a classic vintage set. It’s a modern take on a vintage-style curl as it’s more relaxed and less structured than it would have been originally.

Stylist Kayleigh Fuller from the UK created this look to suit everyone. It is glamorously soft and can be adapted for casual or formal occasions.

To get the best results from a set, great tools and products are a must. Use a small barrel tong to create the curls. Smooth away the frizz and tame the curls into shape using a Suavacita pomade. Finish off the style with a Kenra 25 Volume Hairspray.

This look can be for everyone. Fuller explains, “It’s adaptable and can be more or less structured depending on the client’s style. Long, short, fine or thick hair can be set, it’s finding what works best for you.

Because the final shape is all in the brushing out, there is a style that suits every face shape. It’s all about balance. To wear this vintage pin-up hair daily is fairly high maintenance and requires setting every couple of days for most, but get your set right and it can last for up to a week!

Instagram @destineecushing

#11: Unapologetically Girly

This is a late 1940s look that has the beginning influences of the 1950s in it. According to look creator Destinee Cushing from New York, “This look would tend to be more masculine, but it’s actually feminine and unapologetically girly! The cotton candy colors, bow, and big hair make it fun for me.”

This can work for anyone! Cushing used a fauxnytail or a fake ponytail, so it’s perfect for ladies with at least chin-length hair. It really should work with any face shape and be flattering because the placement of the ponytail adds volume which is complimentary to most faces. Age also isn’t an issue here.

Instagram @bouffantdelacroix

#12: Poodle Do

The Poodle Do is the style in this photo. It was recreated by stylist Magic Michael Davids and made famous in the 1940s and 1950s on celebrities such as Lucille Ball and Betty Grable. Those were the decades of ultimate feminine style where ladies would go to the hair salon and get their hair set in curls and dressed out using skilled techniques that have nearly been lost today. The invention of the straightening iron may have contributed to this.

The Poodle Do is a tight and elegant hairstyle where the lady’s hair is first set in curls. The curling techniques vary as to whether you use traditional or modern techniques. Both achieve good results, but vary slightly in the finished result.

The Poodle Do is a very versatile hairstyle to achieve as it can be created with most hair types and lengths, from just above the shoulders to hair that is midway down the back. It all depends on your ability to handle minimal hair (perhaps using a few hair extensions to pad the top out) or long hair (hiding excess hair by overlaying the hair as you wind it up into curls).

Credit: Barberia Salon Hairdressers

#13: Crimped Upside Down Braid

Hair Cindy Hemslee, Makeup Clandia Alvarado for William Wesley Grand Salon and Spa, Davenport, IA

#14: Pomped Braid

Credit: Cutting Loose Salon

#15: Mohawk Curls

Credit: Cutting Loose Salon

#16: Band Illusion

Credit: Cutting Loose Salon

#17: Buns and Pin Curls

Credit: Cutting Loose Salon

#18: Old Hollywood Waves

How To Style:

Create a deep side parting.
Apply thermal protection to dry hair.
Curl sections and curl them as uniformly as possible. Make sure they are the same size sections and curled all the same direction.
Once you have curled all sections of hair and they have all cooled, use a dressing brush to brush through the curls until they form into a wave.
To make the ridges more prominent, lightly tease once underneath each one.
Once you are happy with the shape, set the style with some finishing spray.

Recommended Products:

Caviar Perfect Iron Spray protects hair from the heat of the iron up to 450 F.

Best Face Shape and Hair Type:

All face shapes with hair that is medium in texture and density will suit this hairstyle best.

42 Pin-Up Hairstyles That Scream “Retro Chic” (Tutorials Included)

#1: Sassy Pin-Up Beehive

#2: Classic 50s Style

#3: Modern Victory Roll

#4: Modern Flapper

#5: Classic Retro Glam

#6: Double Victory Roll

#7: Modern Femme Fatale

#8: Dry Finger Waves

#9: Hidden Pin Curl Swirl

#10: Classic Vintage Set

#11: Unapologetically Girly

#12: Poodle Do

#13: Crimped Upside Down Braid

#14: Pomped Braid

#15: Mohawk Curls

#16: Band Illusion

#17: Buns and Pin Curls

#18: Old Hollywood Waves

#19: THIS ABOVE ALL

#20: THE WATCH(WO)MEN

#21: A STAR IS BORN

#22: TO CATCH A THIEF

#23: LOVE AFFAIR

#24: THE FARMER’S DAUGHTER

#25: A FREE SOUL

#26: FOLLOW THE FLEET

#27: COQUETTE

#28: PILLOW TALK

#29: GENTLEMEN PREFER BLONDES

#30: COVER GIRL

#31: SPITFIRE WOMAN

#32: AIR HOSTESS

#33: REAR WINDOW

#34: SOME LIKE IT HOT

#35: ANCHORS AWEIGH

#36: A PLACE IN THE SUN

#37: NONE BUT THE LONELY HEART

#38: BLUE HAWAII

#39: CRYBABY

#40: FOREVER, DARLING

#41: HOW THE WEST WAS WON

#42: IT HAPPENED ONE NIGHT