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Now Reading 30 Pin Up Hairstyles That Scream “Retro Chic”

30 Pin Up Hairstyles That Scream “Retro Chic”

What goes around comes around. Bless your lucky stars the obsession with all things vintage continues! 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

  • #1 Crimped Upside Down Braid

    Written by Shannel Mariano

    The crimped texture on the hair gives this pin up-inspired upstyle more interest.

    How To Style:

    1. Apply thermal protection to dry hair.
    2. Crimp the hair using a crimper.
    3. With your head upside down, French braid your hair starting from the bottom, working your way upwards towards one side on the of the top of your head.
    4. From there, continue French braiding to the side.
    5. Once your run out of hair to pick up to add to the French braid, continue braiding backwards and secure with an elastic band.
    6. Tuck the braid not attached to the scalp into hair in the back.
    7. Secure with a bobby pin.
    8. Set with a finishing spray.

    Recommended Products:

    Perfect Iron Spray protects hair from thermal irons up to 450 F.

    Best Face Shape and Hair Type:

    Wider face shapes with hair that is medium in texture and high in density will suit this style best.

  • #2 Pomped Braid

    Written by Shannel Mariano

    This combination of color, curls and braids gives this upstyle so much texture. The front has some height, giving the illusion of length for the face.

    brown-hair-pin-up

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

    cute-back-view-of-pin-up-hairstyle

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

    How To Style:

    1. Give the hair some texture and grit using styling products on dry hair.
    2. Lightly tease a triangle section of the front and set it with hairspray.
    3. Gently and carefully begin to French braid the hair on top, including the hair that was teased. Do not include hair on the sides of the head, just the Mohawk section all the way to the back.
    4. Secure the braid with an elastic band.
    5. Pin up the braid using a bobby pin.
    6. Curl the hair on the sides.
    7. Gently and loosely pull them back and pin them into the braid.
    8. Set with a finishing spray.

    Recommended Products:

    Caviar Perfect Texture Spray gives the hair a great foundation for upstyles.

    Best Face Shape and Hair Type:

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

  • #3 Mohawk Curls

    Written by Shannel Mariano

    This easy-to-recreate upstyle is basically just three ponytails lined up vertically and curled into a Mohawk!

    How To Style:

    1. Apply a product for texture and grit on dry hair.
    2. Create three ponytails lined up vertically on the Mohawk section of the head.
    3. Curl the ponytails.
    4. Pin them in place using bobby pins.
    5. Apply a product for shine.

    Recommended Products:

    Alterna’s Bamboo Kendi Dry Oil Micromist Spray gives the hair shine without affecting the hold of hairspray on hair.

    Best Face Shape and Hair Type:

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

  • #4 Band Illusion

    Written by Shannel Mariano

    This vintage-inspired hairstyle is a great way to dress up shorter hair. The crown is teased up high and a hairband is worn around the head, keeping the shorter pieces tucked and giving the profile a great shape.

    How To Style:

    1. Tease sections of hair on the crown area and set it with hairspray.
    2. Carefully put a headband around the hair.

    Recommended Products:

    Caviar Anti-Aging Extra Hold Hairspray gives the hair ultra-firm control while protecting the style from humidity.

    Best Face Shape and Hair Type:

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

  • #5 Buns and Pin Curls

    Written by Shannel Mariano

    This sleek upstyle consists of a high bun and a very clean, beautiful detail of hair sweeping away from the face.

    How To Style:

    1. Create a deep side parting.
    2. Section out the hair on top of the head from the parting to the parietal ridge on the other side.
    3. Gather all the other hair into a high ponytail and secure with an elastic band.
    4. Lift and lay the ponytail over the top of the head.
    5. Pin hair padding over the ponytail above the base of the ponytail.
    6. Let the ponytail fall over the hair padding and completely cover it.
    7. Put an elastic on the ponytail right underneath the padding to secure the hair over the padding.
    8. Lightly and gently tuck the elastic slightly underneath the padding to cover it and pin it in place with a bobby pin.
    9. Shape the remaining hair from the ponytail into different pin curls on one side of the head and secure them with bobby pins.
    10. Release the hair that was sectioned out on top of the head.
    11. Sweep the hair backwards and create pin curls with them, placing them towards the other pin curls created from the ponytail.
    12. Set the hairstyle with hairspray.
    13. Apply a shine spray to the hair.

    Recommended Products:

    Alterna’s Bamboo Kendi Dry Oil Micromist gives the hair shine without breaking down hairspray on the hair.

    Best Face Shape and Hair Type:

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

    Tip:

    You can buy hair padding from any beauty supply or online.

  • #6 Old Hollywood Waves

    Written by Shannel Mariano

    These beautiful waves are classic and definitely never go out of style.

    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.

  • #7 THIS ABOVE ALL

    Written by Tanya Ramirez

    Victory rolls are a quintessential aspect of vintage hairstyles. Polished perfection!

    Pin Up Hairstyles

    Photo credit: Shutterstock.com

    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!

  • #8 THE WATCH(WO)MEN

    Written by Tanya Ramirez

    Get inspired by this delightful ‘do, reminiscent of super-heroine Silk Spectre aka (Sally Jupiter).

    Vintage Rolled Pin Up Hairstyle Updo

    Photo credit: Shutterstock.com

    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.

  • #9 A STAR IS BORN

    Written by Tanya Ramirez

    A little goes a long way with pin up hairstyles. Keep hair soft and simple and enhance your look with dramatic makeup.

    Soft Simple Pin Up Hairstyle with Bow

    Photo credit: Shutterstock.com

    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.

  • #10 TO CATCH A THIEF

    Written by Tanya Ramirez

    Ring in the summer season wearing this eye-popping look with a hint of mystery.

    Pin Up Hairstyle for Summer with Big Bow

    Photo credit: Shutterstock.com

    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.

  • #11 LOVE AFFAIR

    Written by Tanya Ramirez

    Soft, romantic hair is timeless. Update your look with soft, face-framing tendrils.

    Soft Romantic Vintage Hairstyle with Face Framing Tendrils

    Photo credit: Shutterstock.com

    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.

  • #12 THE FARMER’S DAUGHTER

    Written by Tanya Ramirez

    This sweet curly ‘do is innocence and class rolled into one.

    Sweet Curly Pin Up Hairstyle with Red Bow

    Photo credit: Shutterstock.com

    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.

  • #13 A FREE SOUL

    Written by Tanya Ramirez

    These are perfect curls for a trip to the soda fountain on a Saturday night. Super sweet!

    Sweet Pin Up Curly Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #14 FOLLOW THE FLEET

    Written by Tanya Ramirez

    Amp up that bob with this softly curled pin up hairstyle that’s guaranteed to keep those heads turning.

    Softly Curled Bob Pin Up Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #15 COQUETTE

    Written by Tanya Ramirez

    A gorgeous silhouette is certain to be admired. Give your hair a high gloss kick for that extra vintage vibe.

    Dark Glossy Pin Up Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #16 PILLOW TALK

    Written by Tanya Ramirez

    Be ready for that important call with this look that easily transforms from day to night.

    Day to Night Pin Up Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #17 GENTLEMEN PREFER BLONDES

    Written by Tanya Ramirez

    Baby blonde waves don’t lie. This look will have you taking numbers!

    Pin Up Hairstyle with Blonde Waves

    Photo credit: Shutterstock.com

    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.

  • #18 COVER GIRL

    Written by Tanya Ramirez

    The spotlight will be on you with this voluminous pin-curled style.

    Voluminous Pin Curled Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #19 SPITFIRE WOMAN

    Written by Tanya Ramirez

    This is a clean, simple and easy pin up-inspired style. Sometimes that’s all it takes to get noticed!

    Clean Simple Easy Pin Up Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #20 AIR HOSTESS

    Written by Tanya Ramirez

    Take things to a new level with this fun and sassy, 1940’s inspired hairdo.

    Fun Sassy 1940s Hairstyle

    Photo credit: Shutterstock.com

    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!

  • #21 REAR WINDOW

    Written by Tanya Ramirez

    This softly deconstructed after-hours hairstyle offers intrigue into the day’s affairs.

    Softly Deconstructed Pin Up Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #22 SOME LIKE IT HOT

    Written by Tanya Ramirez

    When frizz is your enemy, keep it smooth and controlled with this cute updo.

    Cute Vintage Updo with Scarf

    Photo credit: Shutterstock.com

    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.

  • #23 ANCHORS AWEIGH

    Written by Tanya Ramirez

    You’ll be ready to set off on new adventures with this adorable pin up-inspired hairstyle.

    Long Vintage Hairstyle with Bangs

    Photo credit: Shutterstock.com

    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.

  • #24 A PLACE IN THE SUN

    Written by Tanya Ramirez

    Catch some rays with this tropical-inspired hair design.

    Tropical Inspired Vintage Hairstyle with Rose

    Photo credit: Shutterstock.com

    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.

  • #25 NONE BUT THE LONELY HEART

    Written by Tanya Ramirez

    You’ll certainly find love in all the right places with this sweet look.

    Long Blonde Sweet Vintage Hairstyle

    Photo credit: Shutterstock.com

    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.

  • #26 BLUE HAWAII

    Written by Tanya Ramirez

    This look will have you ready to Rock-a-Hula with your favorite island baby.

    Long Red Vintage Hairstyle with Bangs

    Photo credit: Shutterstock.com

    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.

  • #27 CRYBABY

    Written by Tanya Ramirez

    Take no prisoners with this Wanda Woodward-inspired hairstyle.

    Long Curled Vintage Pin Up Look with Bangs and Bow

    Photo credit: Shutterstock.com

    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.

  • #28 FOREVER, DARLING

    Written by Tanya Ramirez

    Capture an era with this slick style that’s smart and classy.

    Classy Slicked Back Vintage Pin Up Hairstyles

    Photo credit: Shutterstock.com

    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.

  • #29 HOW THE WEST WAS WON

    Written by Tanya Ramirez

    Explore new horizons with this classic look that’s both wild and twisted.

    Classic Vintage Look with Curls

    Photo credit: Shutterstock.com

    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!

  • #30 IT HAPPENED ONE NIGHT

    Written by Tanya Ramirez

    Get ready for that closeup with this decadent style.

    Decadent Pin Up Hairstyle with Curls

    Photo credit: Shutterstock.com

    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!