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

Pin up hairstyles

Pin up hair is a hairstyle that’s considered an updo hairstyle. The hair or part of it is evenly rolled up or styled in smooth, big waves. Pinned-up hairstyles are perfect for vintage-lovers out there. These styles works best on longer hair, but can still be achieved on shorter hair.

Pin-up hairstyles exude a feminine charm and mystique that’s hard to match. Smooth upswept rolls, baby bangs, waves, and perfectly coiled locks are the epitome of vintage hair. While these styles may seem complicated, with a little practice, our pin up hairstyles are actually quite easy to master.

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A Sassy and Sexy Pin-up Beehive
Instagram @emilyolyvia

#1: Sassy and Sexy Pin Up Beehive

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

#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.

#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!

Modern Flapper 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.

#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.

#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!

Modern Femme Fatale hairstyle
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!

Dry Finger Waves hairstyle
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!

#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.

Classic Vintage Set hairstyle
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!

Unapologetically Girly hairstyle
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.

#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).

#13: Crimped Upside Down Braid

brown-hair-pin-up
Hair Cindy Hemslee, Makeup Clandia Alvarado for William Wesley Grand Salon and Spa, Davenport, IA

#14: Pomped Braid

#15: Mohawk Curls

#16: Band Illusion

#17: Buns and Pin Curls

#18: Old Hollywood Waves

How To Style:

  1. Create a deep side parting.
  2. Apply thermal protection to dry hair.
  3. Curl sections and curl them as uniformly as possible. Make sure they are the same size sections and curled all the same direction.
  4. 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.
  5. To make the ridges more prominent, lightly tease once underneath each one.
  6. 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.

Pin Up Hairstyles
Photo credit: Shutterstock.com

#19: THIS ABOVE ALL

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a severe center part, then divide hair into three sections: right, left and back.
  3. Begin on the right side and brush the area smooth. Use a light hold gel or light spray wax for control and to tame any flyaways. Take the ends and begin rolling upward towards the head in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins.
  4. Repeat the steps noted above on the left side. Be sure your rolls are symmetrical. Smooth the exterior of both rolls with a fine tooth comb and light hairspray.
  5. Next, brush hair smooth in the back area. Backcomb the base interior of the hair from the nape downward. Gather ends then tuck and roll under and upwards towards the nape to create your style. Secure at the base of the neck using bobby pins.
  6. Finish with a hard-hold/high shine hairspray.

Recommended Products:

Try TIGI Bed Head HARD HEAD Hairspray for superior hold and high shine.

Best Face Shape and Hair Type:

This look is suitable for oval, square and round face shapes. This style works best on medium to thick hair.

Tip:

Accent with Kevin Murphy’s COLOR.BUG for that extra glow!

Vintage Rolled Pin Up Hairstyle Updo
Photo credit: Shutterstock.com

#20: THE WATCH(WO)MEN

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Begin with the fringe area. Create a horizontal parting and brush hair forward. Backcomb the underside interior of the hair. Gather ends and roll under to create your fringe roll. Use a hair donut, padding or gentle backcombing for extra support. Pin under as needed with bobby pins. Smooth the exterior of the fringe with a fine tooth comb and light hairspray.
  3. Now, divide hair into three remaining sections: right, left and back area.
  4. Begin on the right side and brush the area smooth. Use a light hold gel or light spray wax for control and to tame any flyaways. Take the ends and begin rolling upward toward the head in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins.
  5. Repeat the steps noted above on the left side. Be sure your rolls are symmetrical. Smooth the exterior of both rolls with a fine tooth comb and light hairspray.
  6. Next, brush hair smooth in the back area. Backcomb the base interior of the hair from the nape downward. Gather ends then tuck and roll under and upwards toward the nape to create your style.  Secure at the base of the neck using bobby pins.
  7. Finish with a hard-hold/high shine hairspray.

Recommended Products:

Try Kevin Murphy SESSION.SPRAY for flexible hold with anti-humidity protection.

Best Face Shape and Hair Type:

This look is suitable for oval, round and square face shapes. This style works best on medium to thick hair.

Tip:

Add a bejeweled barrette to accent your look.

Soft Simple Pin Up Hairstyle with Bow
Photo credit: Shutterstock.com

#21: A STAR IS BORN

How To Style:

  1. Prep damp hair with a light hold volumizing mousse.
  2. Blow dry with a paddle brush or a round brush for extra volume. Flip hair ends up and out as your dry.
  3. Create a soft side parting. Take the left side and style up and away from the face. Twist gently to create a bit of volume. Secure with a bobby pin.
  4. Next, take the fringe and the right side and sweep up and away from the face. Twist gently for extra volume then secure with a bobby pin.
  5. Smooth any stray hairs and the hairline.
  6. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy BODY.BUILDER Volumizing Mousse for flexible fullness and hold.

Best Face Shape and Hair Type:

This look is suitable for round, square or oval shaped faces. This style works best on fine to medium hair.

Tip:

Accent your style with a small flowers.

Pin Up Hairstyle for Summer with Big Bow
Photo credit: Shutterstock.com

#22: TO CATCH A THIEF

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Take the fringe section and create a slight pompadour. Twist and secure with a bobby pin.
  3. Brush remaining hair smooth and gather into a ponytail. Backcomb the underside interior of hair and roll the ends under and in an upward motion to create a bun. Pin hair at the base of the bun and along the sides as needed.
  4. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy ANTI-GRAVITY volumizer and texturizer for control with oil-free shine.

Best Face Shape and Hair Type:

This look is suitable for oval, square or heart shaped faces. This style works best on medium hair.

Tip:

Accent this look with an oversized hair bow.

Soft Romantic Vintage Hairstyle with Face Framing Tendrils
Photo credit: Shutterstock.com

#23: LOVE AFFAIR

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a clean side parting then divide hair into three sections: right, left and back areas.
  3. Begin on the right side and brush the area smooth. Use a flexible hairspray for control and to tame any flyaways. Take the ends and begin rolling upward toward the head in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins. Keep the finish soft and romantic.
  4. Repeat the steps noted above on the left side, incorporating the fringe as well. Be sure your rolls are neat and soft. Smooth the exterior of both rolls with your fingers and light hairspray.
  5. Next, brush hair smooth in the back area. Create soft spiral curls with a large barrel iron. Curl hair from the ends up through the mid length of the hair in a vertical fashion. Release curls and allow to fall softly.
  6. Pull a few soft tendrils to frame the face. Curl as needed.
  7. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy FRESH.HAIR for perfect next-day hair.

Best Face Shape and Hair Type:

This look is suitable for round, oval or square shaped faces. This style works best on medium to thick hair.

Tip:

Define your face-framing tendrils with a light hold wax.

Sweet Curly Pin Up Hairstyle with Red Bow
Photo credit: Shutterstock.com

#24: THE FARMER’S DAUGHTER

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a clean side parting then divide hair into three sections: right, left and back.
  3. Begin on the right side by taking 1-inch vertical sections and curl hair using a large barrel curling iron to create large spiral curls.
  4. Repeat the steps noted above on the left side, incorporating the fringe as well. Backcomb the fringe lightly and brush up and away from face then spiral curl hair in a vertical fashion.
  5. Next, brush hair smooth in the back area. Create soft spiral curls with a large barrel iron. Curl hair from the ends up through the mid length of the hair in a vertical fashion. Release curls and allow to fall softly.
  6. Finish with a light hold hairspray.

Recommended Products:

Try Oribe Apres Beach for touchable waves with beautiful shine.

Best Face Shape and Hair Type:

This look is suitable for square, oval or round shaped faces. This style works best on medium to thick hair.

Tip:

Accent with a gorgeous red bow.

Sweet Pin Up Curly Hairstyle
Photo credit: Shutterstock.com

#25: A FREE SOUL

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a clean side parting then divide hair into three sections: right, left and back.
  3. Begin with the fringe area. Create a horizontal parting and brush hair forward. Backcomb the base of the section. Sweep hair back and away from face to create a soft fringe roll. Use a hair donut, padding or gentle backcombing for extra support. Pin under as needed with bobby pins. Smooth the exterior of the fringe with a fine tooth comb and light hairspray.
  4. Next, move the right side and brush the area smooth. Use a flexible hairspray for control and to tame any flyaways. Take the ends and begin rolling upward toward the head in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins.
  5. Repeat the steps noted above on the left side. Be sure your rolls are neat and soft. Smooth the exterior of both rolls with your fingers and light hairspray.
  6. Next, brush hair smooth in the back area. Create soft yet defined spiral curls with a large barrel iron. Curl hair from the mid length through to the ends in a vertical fashion. Release curls and allow to fall softly.
  7. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy YOUNG.AGAIN treatment oil for smooth, shiny hair.

Best Face Shape and Hair Type:

This look is suitable for oval, square and round face shapes. This style works best on medium hair to thick hair.

Tip:

Accent with a delicate hair ribbon.

Softly Curled Bob Pin Up Hairstyle
Photo credit: Shutterstock.com

#26: FOLLOW THE FLEET

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a soft side parting then divide hair into three sections: right, left and back area.
  3. Begin on the right side and brush the area smooth. Use a medium barrel curling iron to create soft spiral curls from roots to ends
  4. Repeat the steps noted above on the left side. Use a medium barrel curling iron to create soft spiral curls from roots to ends
  5. Next, brush hair smooth in the back area. Use a medium barrel curling iron to create soft spiral curls from roots to ends.
  6. Deconstruct curls gently using your fingertips. Backcomb gently for extra fullness.
  7. Finish with a light hold hairspray.

Recommended Products:

Try DermOrganic Windswept DEFINING WHIP for separation and definition with bounce and movement.

Best Face Shape and Hair Type:

This look is suitable for round, oval or heart shaped faces. This style works best on medium to fine hair.

Tip:

Brush curls smooth for a soft, finger-waved look.

Dark Glossy Pin Up Hairstyle
Photo credit: Shutterstock.com

#27: COQUETTE

How To Style:

  1. Prep damp hair with a light hold volumizing mousse.
  2. Blow dry with a paddle brush or a round brush for extra volume.
  3. Create a soft side parting. Take large one to two inch sections and curl hair horizontally using a large barrel curling iron. Secure curls with a pin curl clip and allow to cool.
  4. Continue until all hair is curled. Allow hair to cool for 10 minutes. Release pin curl clips and allow curls to fall. Brush hair smooth using a paddle brush to create soft, glamorous Hollywood waves.
  5. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy STAYING ALIVE Leave-in Conditioner for added protection and flexibility.

Best Face Shape and Hair Type:

This look is suitable for most face shapes. This style works best on medium to thick hair.

Tip:

Gather ends into a chignon for an upswept style.

Day to Night Pin Up Hairstyle
Photo credit: Shutterstock.com

#28: PILLOW TALK

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Take the fringe section and curl hair horizontally using a large barrel curling iron. Backcomb the underside, then take the ends and roll under to create your fringe roll.
  3. Next, brush remaining hair smooth and gather into a high ponytail. Depending on the thickness of your hair, you can use a hair donut to create a bun. If you have thick hair, take your ponytail and twist it lengthwise, then wrap it around to create a bun. Pin hair at the base of the bun and along the sides as needed.
  4. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy BODY.GUARD leave-in creme to smooth and protect hair with extra shine.

Best Face Shape and Hair Type:

This look is suitable for square, oval or heart shaped faces. This style works best on medium to thick hair.

Tip:

Accent with a cute bandana for a casual look.

Pin Up Hairstyle with Blonde Waves
Photo credit: Shutterstock.com

#29: GENTLEMEN PREFER BLONDES

How To Style:

  1. Prep damp hair with a light hold volumizing mousse.
  2. Blow dry with a paddle brush or a round brush for extra volume.
  3. Create a soft side parting. Take large one to two inch sections and curl hair by wrapping around a large barrel curling iron from mid-length to ends.
  4. Continue until all hair is curled. Backcomb fringe slightly and style up and away from face.
  5. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy ANTI-GRAVITY volumizer and texturizer for control with oil-free shine.

Best Face Shape and Hair Type:

This look is suitable for most face shapes. This style works best on fine to medium hair.

Tip:

Accent this look with a small hair bow.

Voluminous Pin Curled Hairstyle
Photo credit: Shutterstock.com

#30: COVER GIRL

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Begin with the fringe area. Create a horizontal parting beginning at the crown and brush hair forward. Gather ends and roll to create your pin curled fringe roll. Pin under as needed with bobby pins.
  3. Then divide hair into three remaining sections: right, left and back areas.
  4. Begin on the right side and brush the area smooth. Use a light hold gel or light spray wax for control and to tame any flyaways. Take the ends and begin rolling hair upward toward the head in a smooth and controlled motion for a smooth ‘C’ shaped curl.
  5. Repeat the steps noted above on the left side. Be sure your rolls are symmetrical. Smooth the exterior of both rolls with a fine tooth comb and light hairspray.
  6. Next, brush hair smooth in the back area. Create soft curls with a medium barrel iron. Curl hair from the mid-length through to ends in a vertical fashion. Release curls and allow to fall softly. Backcomb gently for a soft, voluminous finish.
  7. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy FULL.AGAIN thickening lotion for fullness and body with natural movement.

Best Face Shape and Hair Type:

This look is suitable for oval, round or square shaped faces. This style works best on medium to thick hair.

Tip:

Accent this look with a delicate silk scarf.

Clean Simple Easy Pin Up Hairstyle
Photo credit: Shutterstock.com

#31: SPITFIRE WOMAN

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a slight side parting and take the fringe area comb forward. Backcomb the surface lightly then roll hair back and away from face then secure with a bobby pin.
  3. Then divide hair into three sections: right, left and back areas.
  4. Begin on the right side and brush the area smooth. Use a flexible hairspray for control and to tame any flyaways. Take the ends and begin rolling upward toward the head in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins. Keep the finish soft.
  5. Repeat the steps noted above on the left side, incorporating the fringe as well. Be sure your rolls are neat and soft. Smooth the exterior of both rolls with your fingers and light hairspray.
  6. Next, brush hair smooth in the back area. Backcomb the interior for volume and smooth the surface area. Create soft spiral curls on the ends only with a large barrel iron. Release curls and allow to fall softly.
  7. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy STAYING ALIVE Leave-in Conditioner for added protection and flexibility.

Best Face Shape and Hair Type:

This look is suitable for oval, square and round face shapes. This style works best on medium to thick hair.

Tip:

Gather hair up into a high ponytail for a different look on day two.

Fun Sassy 1940s Hairstyle
Photo credit: Shutterstock.com

#32: AIR HOSTESS

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Begin with the fringe area. Divide the fringe into two sections. Create a horizontal parting beginning at the crown and brush hair forward. Backcomb gently then gather ends and roll to create your stand-up pin curled fringe roll. Take the next fringe section and roll hair to create another stand-up pin curl roll. Secure as needed with bobby pins.
  3. Next, brush hair smooth in the back area. Backcomb the interior for extra volume and keep the surface smooth. Create soft curls with a medium barrel iron. Curl hair from the mid-length through to ends in a horizontal fashion. Set curls using pin curl clips until all hair is curled. Allow hair to cool, then release curls and allow to fall softly. Backcomb gently for a soft, voluminous finish.
  4. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy MOTION.LOTION curl enhancer to define curls with frizz control.

Best Face Shape and Hair Type:

This look is suitable for oval, round or square shaped faces. This style works best on medium to thick hair.

Tip:

Accent with a cute vintage hat!

Softly Deconstructed Pin Up Hairstyle
Photo credit: Shutterstock.com

#33: REAR WINDOW

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a full fringe roll using a large barrel curling iron. Curl hair forward and tuck under. Secure with bobby pins as needed.
  3. Create a soft center parting then begin curling hair using a medium barrel curling iron. Take small to medium-sized sections of hair and curl vertically in alternating directions from the mid-length down through to the ends. Allow curls to cool.
  4. Deconstruct curls gently using your fingertips. Backcomb lightly for extra fullness.
  5. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy UNDRESSED to create a loose, undone and natural look.

Best Face Shape and Hair Type:

This look is suitable for oval, round and heart shaped faces. This style works best on fine to thick hair.

Tip:

Accent with a pretty flower on one side.

Cute Vintage Updo with Scarf
Photo credit: Shutterstock.com

#34: SOME LIKE IT HOT

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Begin with the fringe area. Create a horizontal parting from the crown area down to the ears. Gather hair from the fringe and sides to create a ponytail at the crown. Backcomb the underside interior of the hair. Gather ends and roll under to create your fringe roll. Use a hair donut, padding or gentle backcombing for extra support. Pin under as needed with bobby pins. Smooth the exterior of the fringe with a fine tooth comb and light hairspray.
  3. Next, brush remaining hair smooth and gather into a high ponytail. Take small sections from the ponytail and twist and pin small curls as desired, depending on the thickness of your hair. Secure with bobby pins as needed.
  4. Finish with a light hold hairspray.

Recommended Products:

Try TIGI Bed Head HARD HEAD Hairspray for superior hold and high shine.

Best Face Shape and Hair Type:

This look is suitable for oval, square and heart-shaped faces. This style works best on fine to medium hair.

Tip:

Accent with a cute vintage scarf.

Long Vintage Hairstyle with Bangs
Photo credit: Shutterstock.com

#35: ANCHORS AWEIGH

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a full fringe roll using a large barrel curling iron. Curl hair forward and tuck/roll under. Secure with bobby pins as needed.
  3. Take small sections from the temple area and brush back to secure with a small hair tie.
  4. Curl hair using a large barrel curling iron. Take medium-sized sections of hair and curl vertically in alternating directions from the mid-length down through to the ends. Allow curls to cool.
  5. Deconstruct curls gently using your fingertips. Backcomb lightly for extra fullness.
  6. Finish with a light hold hairspray.

Recommended Products:

Try Oribe Apres Beach for touchable waves with beautiful shine.

Best Face Shape and Hair Type:

This look is suitable for round, oval or heart shaped faces. This style works best on medium to thick hair.

Tip:

Accent with your favorite sailor hat for a nautical look.

Tropical Inspired Vintage Hairstyle with Rose
Photo credit: Shutterstock.com

#36: A PLACE IN THE SUN

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a soft side parting then divide hair into three sections: right, left and back areas.
  3. Begin on the right side and brush the area smooth. Use a flexible hairspray for control and to tame any flyaways. Take the ends and begin rolling up and back away from the face in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins.
  4. Next move to the fringe area. Take the fringe section and curl using a large barrel iron. Backcomb the underside and roll from the ends up. Secure with bobby pins as needed. Smooth the exterior of hair with your fingers and light hairspray.
  5. Next, brush hair smooth in the back area. Create a French twist by gathering ends and rolling hair towards the head in a vertical fashion. Secure with bobby pins as needed.
  6. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy YOUNG.AGAIN treatment oil for smooth, shiny hair.

Best Face Shape and Hair Type:

This look is suitable for oval, square and round face shapes. This style works best on medium hair to thick hair.

Tip:

Accent with an oversized flower pin.

Long Blonde Sweet Vintage Hairstyle
Photo credit: Shutterstock.com

#37: NONE BUT THE LONELY HEART

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a clean side parting then divide hair into three sections: right, left and back areas.
  3. Begin on the right side and brush the area smooth. Use a flexible hairspray for control and to tame any flyaways. Take the ends and begin rolling upward toward the head in a smooth and controlled motion. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins. Keep the finish soft and romantic.
  4. Repeat the steps noted above on the left side. Roll the fringe separately by gathering hair ends and rolling from the ends up to create a soft ‘C’ shaped curl. Be sure your rolls are neat and soft. Smooth the exterior of both rolls with your fingers and light hairspray.
  5. Next, brush hair smooth in the back area. Create two soft, spiral curls on the ends only with a large barrel iron in a vertical fashion. Release curls and allow to fall softly.
  6. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy FULL.AGAIN thickening lotion for fullness and body with natural movement.

Best Face Shape and Hair Type:

This look is suitable for oval, round or square shaped faces. This style works best on medium to thick hair.

Tip:

Accent this look with a fascinator and lace netting.

Long Red Vintage Hairstyle with Bangs
Photo credit: Shutterstock.com

#38: BLUE HAWAII

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a clean side parting. Curl fringe forward using a small barrel curling iron and sweep gently over to one side.
  3. Take the right side and brush hair smooth in an upward fashion and secure with a bobby pin.
  4. Then begin curling hair using a medium barrel curling iron. Take small to medium-sized sections of hair and curl vertically toward the face from the mid-length down through to the ends. Allow curls to cool.
  5. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy BODY.GUARD leave-in creme to smooth and protect hair with extra shine.

Best Face Shape and Hair Type:

This look is suitable for round, oval or heart shaped faces. This style works best on fine to thick hair.

Tip:

Accent with some tropical flowers.

Long Curled Vintage Pin Up Look with Bangs and Bow
Photo credit: Shutterstock.com

#39: CRYBABY

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a mock baby bangs (fringe) roll using a medium barrel curling iron. Curl hair forward and tuck/roll under. Backcomb underside for extra support. Secure with bobby pins as needed.
  3. Sweep sides up and away from face and secure with bobby pins.
  4. Curl remaining hair using a large barrel curling iron. Curl medium-sized sections of hair vertically in alternating directions from the ends up to the mid-length. Allow curls to cool.
  5. Deconstruct curls gently using your fingertips. Backcomb lightly for extra fullness.
  6. Finish with a light hold hairspray.

Recommended Products:

Try DermOrganic Fast Drying Shaping Spray for great hold with touchable texture.

Best Face Shape and Hair Type:

This look is suitable for oval, round and heart shaped faces. This style works best on fine to thick hair.

Tip:

Accent with a cute polka-dot headband.

Classy Slicked Back Vintage Pin Up Hairstyles
Photo credit: Shutterstock.com

#40: FOREVER, DARLING

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Begin with the fringe area. Create a horizontal parting from the crown and brush hair forward. Backcomb the surface of the hair. Gather ends straight up, smooth the underside so you have a smooth surface as you roll hair from the ends down toward the head to create your fringe roll. Use a hair donut, padding or gentle backcombing for extra support. Pin as needed with bobby pins. Smooth the exterior of the fringe with a fine tooth comb and light hairspray.
  3. Next, sweep the sides up and away from face and secure.
  4. Brush hair smooth in the back area. Backcomb the base interior of the hair from the nape downward. Gather ends then tuck and roll under and upwards toward the nape to create your style.  Secure at the base of the neck using bobby pins.
  5. Finish with a hard-hold/high shine hairspray.

Recommended Products:

Try TIGI Bed Head HARD HEAD Hairspray for superior hold and high shine.

Best Face Shape and Hair Type:

This look is suitable for oval, square and round face shapes. This style works best on medium to thick hair.

Tip:

Accent with a vintage lace net.

Classic Vintage Look with Curls
Photo credit: Shutterstock.com

#41: HOW THE WEST WAS WON

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Begin with the fringe area. Create a horizontal parting beginning at the crown and brush hair forward. Gather ends and roll hair to create your pin curled fringe roll.
  3. Next, take hair from the left side temple area and sweep up from the ends to create your next pin curled roll. Secure as needed with bobby pins.
  4. Take any remaining hair from the side areas and sweep up to secure at the crown area.
  5. Brush remaining hair smooth in the back area. Create soft curls with a large barrel iron. Curl hair towards the face from the mid-length through to ends in a vertical fashion. Set curls using pin curl clips until all hair is curled. Allow hair to cool then release curls and allow to fall softly.
  6. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy BODY.BUILDER Volumizing Mousse for flexible fullness and hold.

Best Face Shape and Hair Type:

This look is suitable for round, oval or round face shapes. This style works best on medium to thick hair.

Tip:

Accent with your favorite fancy hat!

Decadent Pin Up Hairstyle with Curls
Photo credit: Shutterstock.com

#42: IT HAPPENED ONE NIGHT

How To Style:

  1. Prep clean, dry hair with a light hold working hairspray.
  2. Create a soft side parting and clip a small fringe section away to start.
  3. To begin your three stand-up pin curls, take the center crown section and brush hair smooth. Backcomb the underside, take the hair ends up and roll downward toward the head.
  4. Then take the right section and brush the area smooth. Use a light hold gel or light spray wax for control and to tame any flyaways. Take the ends and begin rolling hair upward toward the head in a smooth and controlled motion for a smooth ‘C’ shaped curl.
  5. Repeat the steps noted above on the left side. Be sure your rolls are symmetrical. Smooth the exterior of both rolls with a fine tooth comb and light hairspray.
  6. Take any remaining hair from the sides and sweep them back away from the face and secure with bobby pins.
  7. Return to the small fringe section and smooth over to one side and pin into place.
  8. Next, brush hair smooth in the back area. Create soft curls with a large barrel iron. Curl hair from the mid-length through to ends in a vertical fashion toward the face. Release curls and allow to fall softly. Backcomb ends gently for a soft, voluminous finish.
  9. Finish with a light hold hairspray.

Recommended Products:

Try Kevin Murphy FRESH.HAIR for perfect next-day hair.

Best Face Shape and Hair Type:

This look is suitable for round, oval or square shaped faces. This style works best on medium to thick hair.

Tip:

Set your look with a light hold spray wax.

Now you have plenty of eye-catching pin up hairstyles to wear all calendar year. Get inspired by the screen sirens of yesteryear and get dolled up with these gorgeous glam looks!




Posted In: Hair Trends