Trends may come and go, but our vintage obsession is clearly here to stay. We love everything retro and everything retro seems to love us. That’s right. Pin up hairstyles, first and foremost, the epitome of vintage, have a certain je ne sais quoi about them. They’re all about the over the top feminine look, that one can only achieve via victory rolls, baby bangs, and upswept curls. So get your pins out girls, because today we’re going full vintage!
1. The Ash Blonde Pin Up Hairstyles
Say hello to your next Halloween costume. Or your next party getup. Either way, you cannot possibly go wrong with this gorgeous ash blonde color pinned up in a loose victory roll on top of your head. Skeleton hands optional, of course.
2. The Classy Pin Up Hairstyles
Here’s a very classy and subdued way in which you can wear pin up in your everyday life. Since this is not the 50s anymore, it might seem a bit odd when you show up at the office with huge V-rolls. Not like this, however. The orange lipstick is always a win.
3. Lavender Victory Rolls
Modern meets pin up when two simple victory rolls are here to display a fabulous lavender hair color. Part your hair down the middle and use your iron curler for a few soft waves at the bottom.
4. Pink and Ivory Pin Up Hairstyles
Looking for some extra va-va-va-voom? You just found it. Not only is this pin up gone wild, but the hair color is an ice-cream swirl as well. It’s a combination of bright peony pink with lavish ivory on the sides. The rose is an outstanding touch.
5. Sea Foam and Bows
Another significant aspect of the pin up hairstyles trend is the bangs. Here’s an excellent example of very short and soft bangs, in a smashing sea foam color. One fabulous way to bring it out is by sporting a jumbo, retro, dark coral turban with a bow.
6. Vixen Pin Up Hairstyles
Pin up for a night out with this vixen attire. Everything about this screams sensuality, starting with the hair and makeup. The two asymetrical jumbo victory rolls elongate the face and add some height to your figure.
7. Perfection in a Pic
Another way of wearing your hair is by using a lot of bobby pins to create roses all over your head. It does take a little practice and a lot of hairspray, but just look at how perfect the result is.
8. Rockability Pin Up Hairstyles
Who says mermaids didn’t pin up? Just take a look at this wonderful washed up seaweed green hair color for inspiration, and you’ll understand. The lesson here is that you shouldn’t be afraid to mix the pin up trend and the mermaid trend for a spectacular result.
9. Katy Perry Pin Up Hairstyles
The queen of transformations herself, this modern day Madonna, Katy Perry is no stranger to the pin up trend. Here she is sporting a delicious shade of bubble gum pink hair that highlights her blue eyes and two perfect victory rolls at the front.
10. The Artistic Pin Up Hairstyles
If you’re artsy and creative, you can put that side of you to good use and come up with amazing hairstyles. This low unicorn victory roll with a neon baby blue streak will be the talk of every party.
11. Messy Pin Up Hairstyles
If you’re in a hurry or just a lazy girl, then you’re on our team. Join the modern trend and go for a loose coil on the side of the head rather than the perfectly polished rolls our great grandmas used to wear. Welcome to the new century!
12. The Cristina Aguilera
Another favorite celebrity who is very partial to the pin up age is singer X-tina. Her ice blonde hair perfectly complements her blue eyes and red lips. She loves victory rolls as well, which she wears every chance she gets.
13. Simple Pin Up Hairstyles
All you need to pull off this look are a few bobby pins. Choose the strands of hair that usually hug your face and coil them up on top of your head. Fill in your eyebrows to contour your face and use a dark, matte lipstick for this look.
14. Teal, Green, and Jewels
This is pin up meets formal wedding. Yes, you don’t have to give up your favorite trend even when you’re invited to a very formal event. Run the rolls to one side, create small ‘birds’ nests’ and fill them with eye-catching jewels.
15. Lazy Holiday Pin Up Hairstyles
We love this hairstyle because it reminds us of Madonna in her early years. It’s also very much pin up girl gone on holiday. All you need is some mousse for your hair to give it texture and make sure it stays in place. Add a lovely head scarf for fun.
16. Retro Meets Hipster
With this look, you get your grandma, and your young self all rolled into one. How cool is that? It’s just like you Nana, with her hair rolls and winged eyeliner decided to sport a nose ring and black nail polish. Awesome!
17. Neon Pin Up Hairstyles
If you want to take pin up one step further, all you need to do is dye your hair in a neon color. Take this shade of cobalt blue, for example. The short bangs and the sweet pink bow will have you looking like a modern day Lolita in no time.
18. Snow White, Is that You?
Yes, we believe it is. Could Snow White look even prettier than she already did in her Disney movie? Yes. If she went all pin up. Here’s a style in the classic Snow White blue and red color combination that will transform you into a princess. Watch out for the Evil Queen!
19. Forest Green Pin Up Hairstyles
Here’s another hair color that captured out heart forever. Forest green. The black and white skinny scarf and small roll at the front do it justice as well.
20. Mint Green Pin Up Hairstyles
In case you need something on the softer side, however, maybe mint green is the shade for you. Pair it with powdery pink and you’ll be a bonbon ready to eat. Talk about 50s glamour!
21. Ariel Pin Up Hairstyles
We’ve had Snow White, now it’s Ariel’s turn. If she had lived in modern times, and were prone to the vintage trend, this is how she would have worn her hair. In beautiful, perfect, red victory rolls, complete with cat-eye sunglasses.
22. The Birdcage
Not the movie, the accessory. No special occasion pin up look is complete without a birdcage, and you know it. The combination between the black intricate pattern covering your eyes and the sultry red lipstick will prove charming beyond belief.
23. Beautiful Bangs
A lovely trick for elongating your face is to have your stylist cut your bangs in a V. Use your curler to give them some volume. The high rolls are a must here as well, for they add some height to your figure.
24. Red Roses
Wear a red rose behind your ear to complement your lips. It creates a lovely chromatic balance at face level, that will make you look like a walking painting. The winged tips are a must, as are the false eyelashes.
25. Matching Eyebrows
If you want to pull off this look, you have two options. You can dye your natural eyebrows in the same shade as your hair. Or you can shave them off and use a special colored pencil to draw them back on. The choice is yours!
26. Next Level Pin Up Hairstyles
Why stop at only a few rolls when you can have them all over your head? This is more of a party look coming to us from the 40s and 50s. Think vintage couture Dior and you’ll understand what this look is all about. The ‘New Look.’
27. Ice Blonde Pin Up Hairstyles
The great thing about having ice blonde hair when you’re into the pin up trend is that it really highlights your makeup. It becomes a blank canvas for your black eyeliner and red lipstick, showing them off like nothing else can.
28. Short and Heavy Bangs
If you’re looking for pin up hairstyle ideas, don’t be afraid to go all out on your bangs. With this trend, they typically need to be medium sized, one layered, straight, and very heavy. You also need to curl them a bit.
29. Bumper Bangs Pin Up Hairstyles
Let’s talk about bangs some more. Here is a perfect example of bumper bangs. Pro tip – it’s best to attempt your bumper bangs one or two days after you’ve washed your hair. It’s a lot easier to make the beehive stand in its place if the strands are a tad dirty.
30. Bubblegum Pink Pin Up Hairstyles
Pink on top, red on the bottom. This is how we could describe the perfect tableau that is your head once you decide to don this shade of hair dye. Don’t be afraid to wear flowers or other hair accessories. Anything to make you look pretty in pink!
31. Headpieces and Pin up
Glam it all up by using a one of a kind headpiece. You know what the great thing about this idea is? That you can create the headpiece at home. That’s right. Take a button you don’t need anymore, a bit of lace from an old dress, some pretty fabric from another, sew them together and you’re good to go!
32. The Scarlet Johansson
Even Black Widow herself fell prey to the lovely vintage trend. Here she is sporting some lovely upturned victory rolls. Notice how they continue in one, giant roll all-round the back of her head.
33. The Red Snood
We cannot possibly talk about pin up hairstyles without mentioning snoods. They were the epitome of style back in the day and you can wear them again if you want to. Buy them online or crochet them yourself. There are tons of tutorials and knitting patterns on the internet.
34. Pin Up Hairstyles for Long Hair
Go wild with this messy hairdo. All you need to do is start off with the good old victory rolls at the top and soft curls at the bottom. Then take your hairbrush and tease at the hair until you get the desired result. Remember, the messier, the better.
35. Molten Copper Swirls
Now this is a beautiful hair color if we’ve ever seen one. Needless to say, it is in superb highlight, thanks to the one and only pin up trend. The unicorn roll at the front perfectly showcases the ombre copper shade. At the same time, the decadent old Hollywood curls at the bottom are a touch of class.
36. In Flames
What goes well with flaming red? Why, more red, of course. Don’t be afraid of solid blocks of color, even when it means your hair and your clothes. However, if you do want to break the pattern a little, you can do so with your accessories. Notice the white, thick, plastic sunglasses in our example.
37. Vintage Perfection
Remember the Old Hollywood sirens of the silver screen back in the 40s, with their perfect makeup and hair? You can be one of them as well, thanks to our beloved pinup hairstyles. A touch of eye shadow, a little mascara, some eyeliner, and a lot of rouge complete the look.
38. The Amber Heard
And speaking of Hollywood sirens, here is Amber Heard herself, sporting a toned-down version of the pin up hairstyle. Complete with wing tips, red lipstick, and animal print top, the actress turns heads wherever she goes.
39. Medium Length Pin Up Hairstyles
Proof that this trend works for every hair length there is, here is a shoulder cut. The lovely jumbo curls add some volume to the hairdo. On the other hand, the red rose is simply romantic perfection.
40. The Fauxhawk
As you might have noticed, it’s not just a fauxhawk, but it’s a double rose one. That means double the sensuality and the coolness. Use as many bobby pins as necessary to make everything stand up. However, make sure you hide them underneath the rolls themselves and out of sight.
41. The Lolita Pin Up Hairstyles
Throwing red bows in your blonde hair and using copious amounts of red lipstick should come with a warning. Caution! Might cause a serious case of Lolita! All the better for us, because the Lolita look has always been somewhat of a fashion icon.
42. The Rihanna
The good girl gone bad sometimes goes vintage as well. Like in the case of this red carpet appearance when she tied down her luscious and fiery curls with a pin up bandana. The sweetheart neckline and golden jewelry add to the total effect.
43. The Short Pin Up Hairstyles
There are pin up hairstyles for short hair as well. All you need to do is break out your curling iron and put it to good use. We especially liked this amazing 40s do complete with a kimono-inspired blouse and a large pink peony above the temple.
44. Nude Pin Up Hairstyles
The nude trend has really taken shape in the past couple of years. We now love everything in shades of nude – clothes, makeup, nail polish, and so on. But did you know you can combine it with the glamorous pin up? Just look how pretty and feminine the result is.
45. White Hair, Don’t Care
Already got white hair? Then this is the trend for you. You don’t have white hair? Then you need to dye it right now. It’s the one hair color that transitions seamlessly from one season to the next, without you having to worry about it.
46. The Janelle Monae
The pin up trend is so powerful that even the black and white Janelle Monae jumped on it. Just look at how wonderful she looks in her signature two non-colors, one jumbo victory roll on top of her head, and a striking matte coral lip.
47. Three Rolls to Go, Please
The more rolls you can fit on you head, the better. Pin up is all about going over the top and embellishing yourself. Therefore, grab those curlers and start practicing as soon as possible!
48. Two Toned Pin Up Hairstyles
Highlight your beautiful locks by adding some well-placed peekaboos. They will give the illusion of volume and depth, which is particularly good, especially if you happen to have fine hair.
49. The Comb Over
Another way of doing your hair the pin up style is by combing it all over the crown of your head and tying it in the back. Create some soft curls at the tips and pin a large flower of your choosing on one side.
50. Victory Rolls and Dreads
Here is the true mix of modern and vintage – pin up hairstyles and dreads. All in an amazing moss green shade that will highlight your eyes and put all other hair colors to shame.
What about you? Have you experienced with pin up hairstyles? If so, why don’t you tell us all about it in the comment section below? Relive the glamour and fun of the 50s and share it with us.
Richard is fascinated by everything that has to do with styling techniques and how technology can play an important part in the industry’s development. He started out his career as a barber, and later found his passion for both men and women’s hairstyles. Richard now works as a writer for fashion magazines, blogs, and is actively taking steps toward launching his own online platform!