40 Vintage Pin Up Hairstyles Every Women Should Try At Least Once

Variations of the vintage pin up hairstyle have been present dating back to the 1890’s. It was popular during the 20’s, 40’s, and 50’s and is ready to make another comeback this century. Give your look a retro twist with some of these gorgeous pin up hairstyles.

Half Up Victory Rolls

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Victory rolls were seen as patriotic and were extremely popular during the 1940’s. This look allows you to keep your long locks flowing while pinning up Victory rolls with some serious volume.

Ponytail with a Bow

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It’s all about the accessories with pin up hairstyles. A simple ponytail is dressed up and given a retro twist with a bold red bow. Don’t forget to wear some matching red lipstick!

Side Pin Up

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This is considered a more formal pin up hairstyle. African American trendsetters such as Lena Horn and Dorothy Dandridge made this hairstyle popular and inspired women everywhere to embrace their inner starlet.

Gray with Blunt Bangs

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Update a vintage hairstyle with a funky hair color. This hairstyle uses a beautiful sheer gray to give it an edgy look. Loose round curls and bluntly chopped bangs are reminiscent of the pin up style.

Smell the Flowers

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This hairstyle draws inspiration from the Vargas girls with a low updo and pin up bangs. Add some flowery accessories to make the look ultra feminine.

White and Purple

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Just look at how gorgeous this hairstyle is with these defined colors. The contrast of the purple and white is just amazing, especially when curled and pinned up!

Medium-Length Curled Pin Up

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Pin up hairstyles look great with both long and medium length hair. This beautiful hairstyle has defined curls and curved bangs. The blooming flower really pulls the look together.

Green Curls

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To make any pin up look more modern, consider adding a bold and unique color! We can guarantee women ni the 20th century sported green hair.

Pin Up Hairdo for Long Hair

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You can make a pin up hairdo with almost any modern hairstyle. This simple style pulls back bangs away from the face and pinned. Make sure to tease the crown to get some extra volume. Curl the rest for a bouncy style.

Retro Box Braids

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Style your braids into a pin up hairstyle. This particular hairstyle has only half of the hair pulled up. Accessorize with a flower or other accessory to make the hairstyle really pop.

Blonde Curls

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Pose as Marilyn Monroe with this beautiful blonde hairstyle. The spiral curls are bouncy and give life to your hair. It was trendy back in the 1950’s and it’s still trending now!

Side Pin with a Bandana

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A bandana is the perfect accessory to any pin up hairstyle. This side pin up style is both flirty and sophisticated. Try your best to make your bandana match your outfit for the ultimate pin up look.

Half Up with Curls

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Make this adorable hairstyle match your personality by playing around with the size of your curls. They can be large and bouncy or tight ringlets. It’s up to you!

Long Hair with a Scarf

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The pin up hairstyle is super easy and cute. This hairstyle is simply curled, bangs pulled back, and tied off with a bold colored scarf. It doesn’t get any easier than that!

Blonde Bombshell

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There is no limit to volume when it comes to pulling off a pin up hairstyle. This blonde bob is the perfect pin up style, especially if you’re going for a Marilyn Monroe look. The sweeping side bang is just gorgeous!

Mega Victory Roll

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This over sized victory roll is perfect for those women who want to stand out. You’ll need some strong hair product and spray to keep this victory roll standing tall all day long. Top it all off with an adorable scarf or kerchief.

Tight Curls

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This pin up hairdo has tightly defined curls. It’s absolutely adorable! Be daring and dye your hair a bold or pastel color to make the look more modern.

Short Blonde Pin Up

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If you have short, thin hair, then this pin up hairstyle is for you! The soft waves give your hair ultimate volume and hide the fact that it’s thin. It’s vintage and elegant all in one.

The Little Mermaid

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Dive down deep under the sea with this gorgeous red pin up hairstyle. The natural waves and voluminous Victory roll is reminiscent of our favorite little mermaid. Add a big flower to really make your look stand out.

Dark and Sleek

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If major volume isn’t your style, then this subtle pin up look is the way to go. The large defined curls are light and freeing. You still have the retro style of a pin up girl, just a little less harrumph.

Piled High

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Keep cool on those hot summer days with this vintage look. Pile your hair on top of your head in large rolls and curls. Leave a few strands hanging down to frame your face. Wrap it up in a cute scarf. Voila!

Vintage Rolls

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Who wants only one Victory Roll when you can have two? This hairstyle is great for women who love getting attention! It’s fun, retro, and unique all at once. Play around with different colors and highlights to get the most out of his hairstyle.

Wispy Style

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The beauty of pin up styles is that they look great with every hair length. This short hairstyle looks great wrapped up in a polka dot scarf and teased.

The Modern Pin Up

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This look is perfect if you are waiting to wash your hair. With just a few sprays of dry shampoo and a scarf to cover the back, you’re good to go for another day or two!

The Classic Pin Up

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If you’re looking to do an authentic and classic pin up look, you’ve come to the right place. This works best with medium-length hair that hasn’t been washed that day.

Elegant Pin Up

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As intricate as this hairdo looks, it’s as easy as pinning up your gorgeous curls. Literally, just as easy as opening a bobby pin. This look is extremely elegant and a floppy hat makes it that much better.

Loose Victory Rolls

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Your pin up curls don’t have to always be perfect and in formation. This tousled look is relaxed and laid back. It’s perfect for those trying out victory rolls for the first time.

Glamorous and Classy

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You can’t get any more glamorous than this hairstyle right here. The curls are voluminous and have the perfect wave to them. Perfection!

Higher the Better Victory Roll

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This look is perfect for girls with long hair. The curls are extra big and super bouncy. Just look at how high that victory roll is!

Side Swept Curls

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To achieve this look, take a thick barrel curling iron and run wild! Make sure to use hairspray to keep your curls looking perfect all day long.

The Starlet

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Go from pin up girl to starlet with this gorgeous hairstyle. The curls are structured and defined. The bangs are also curled away from the face to show off your beautiful facial features.

Rolled Updo

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These enormous rolls are absolutely stunning! This is the ultimate pin up hairstyle. We dare you to try it!

Vintage Ombre

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Use different colors to give this vintage look a more modern twist. The possibilities are endless!

Rosie the Riveter

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Show everyone how badass you are with this Rosie the Riveter inspired hairstyle. Pin up styles look fantastic with dark hair, as seen above. Tie it all together with a bandana of your choice.

Ultimate Curly Updo

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This pin up style is perfect for spending the day at the beach or by the pool. Pile your hair on top of your head and pin your curls down. It’ll keep you cool, but looking hot!

50’s Flair

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In a rush but still want to look cute? This hairstyle is super easy and very 50’s era. Put your curled hair up in a high ponytail and wrap it up with a scarf. Curl your bangs under for the ultimate vintage look.

The Long Victory Roll

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This victory roll really grabs your attention! It adds tons of volume to your hair. You can see the scarf just barely peeking out from behind it.

Sleek Curls

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Sometimes the perfect pin up style takes a lot of patience. Take this style for example. The structured curls are perfectly in place and gorgeous!

Va-Va-Voom!

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It’s all about volume with this pin up style. It’s so big it’s hard to look away from it!

Retro Curls

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This hairstyle works best for girls with medium length hair. The bangs have some major volume while the rest of the hair is curled to perfection. Try out a pastel color to get the best look.