40 Gorgeous Vintage Hairstyles for a Classic Touch

Vintage hairstyles like pin-up styles remain a popular choice, reflecting their enduring appeal since their rise in the 1940s and 1950s. This look actually dates back to the 1890s and incorporates influences from various decades. Whether you’re after a classic or contemporary twist, there’s a pin-up look to suit any hair length, type, or color. If you’re considering a retro makeover, explore these chic pin-up hairstyles.

Top Pin Up Hairstyles to Try

From voluminous curls to sleek waves, pin up hairstyles offer a range of styles. Consider adding a unique hair color to give your look a modern twist. Here are some standout pin up styles to inspire you:

1. Voluminous Victory Rolls

Victory rolls are iconic from the 1940s, embodying vintage hairstyle glamour. This look combines classic curls with a polished finish.

2. Retro Ponytail with a Bow

If you love hair accessories but aren’t keen on hats, opt for a retro ponytail adorned with a colorful bow to add a playful touch.

3. Classic Starlet Style

Embrace the starlet vibe with a look reminiscent of African American icons like Dorothy Dandridge and Lena Horne, celebrating their influence on vintage hairstyle fashion.

4. Modern Gray Pin Up Hair

Update a retro style with a sleek gray dye job. Pair defined waves with cropped bangs for a contemporary twist on classic pin up aesthetics.

5. Pin Up Hairstyle with Flowers

Inspired by Vargas girls, this style features a polished low updo with pin up bangs, finished with flowers on each side to highlight your features.

6. White and Purple Half Updo

This hairstyle blends modern elements with retro charm, featuring white blonde and purple ombre hair in a half-up style with defined curls and rolled bangs.

7. Curled Mid-Length Pin Up Hair

Even shorter hair can achieve a stunning vintage hairstyle with defined curls and stylish bangs, complemented by a decorative flower.

8. Green Vintage Curls

Add a modern twist to traditional pin up curls with a vibrant green color, and contrast with black bangs for a unique edge.

9. Long Orange Pin Up Hairstyle

For long hair, a simple half-up style with a teased crown and curled ends creates a classic vintage hairstyle with a touch of glamour.

10. Retro Box Braids

Showcase your braids with a pin-up style by opting for a vintage hairstyle-inspired half-updo, enhanced with colorful hair flowers.

11. Medium-Length Pin Up Curls

Channel Marilyn Monroe with blonde curls and bold red lipstick. This look remains timeless, proving pin up styles are as relevant now as ever.

12. Bandana Glam Hairstyle

Incorporate a bandana into your pin-up look for a stylish accessory that adds flair to a long vintage hairstyle.

13. Curly Half-Up Style

Experiment with curl size and shape to create varied pin up looks. Smaller ringlets and an off-center victory roll offer a playful twist.

14. Long Pin Up Hair

Long hair lends itself well to pin up styles. Combine defined curls with a mini pompadour and a red bandana for a classic appearance.

15. Voluminous Blonde Pin Up Hair

Go big with voluminous shoulder-length hair, featuring tousled waves and a sweeping bang flip for a glamorous pin up style.

16. Oversized Victory Roll Updo

For a dramatic pin-up style, try oversized victory rolls in your vintage hair, secured with strong hold hairspray and topped with a stylish kerchief.

17. Pink Hair with Tight Pin Up Curls

Bright pink hair adds a modern twist to defined vintage curls, creating a look that’s both nostalgic and contemporary.

18. Short Blonde Pin Up Curls

Shorter hair can also embrace the pin up look with soft waves that add volume, making the hair appear fuller and more elegant.

19. Flowing Red Pin Up Hair

Bold red hair paired with undone waves and rolled bangs exudes vintage hair charm. Add a large hair flower to complete the look.

20. Sleek Pin Up Waves

If you prefer a less voluminous approach, opt for sleek waves in a vintage hairstyle, defined with a lightweight serum or gel for a refined retro appearance.

21. Retro Updo with Headband

An updo styled with a headband can be as glamorous as loose waves. Gather hair into rolls and add face-framing tendrils for a classic touch.

22. Vintage Half Up Half Down

Enhance your look with two victory rolls and leave bangs out for a striking appearance. The petroleum color enhances the vintage hairstyle’s appeal.

23. Wispy Hairstyle for Short Hair

Short hair can also embrace vintage hair styles with side-swept bangs and a backcombed crown section for a chic pixie look.

24. Second-Day Hair Pin Up Style

Pin up hairstyles are perfect for second or third-day hair. Use dry shampoo, shine serum, and bobby pins to style a signature roll, with a scarf to finish.

25. Classic Pin Up Curls

Soft curls framing the face offer a timeless look, perfect for medium-length hair. This style is ideal for days when skipping shampoo is preferred.

26. Elegant Easy Updo

A glamorous updo for long or medium hair can be achieved with minimal effort. Pin curls and add a hat for a sophisticated finish.

27. Laid-Back V-Rolls

For a more relaxed pin up style, try loose and tousled victory rolls. This easy-to-do look is perfect for beginners.

28. Classically Elegant Pin Up

Aim for a polished appearance with structured curls and a glossy finish. Dark hair colors enhance the shine typical of vintage hair pin up styles.

29. Long Hair with Perfect Curls

For a striking pin up look, combine long curls with a stylish hat, angled perfectly to complement the big rolled curl.

30. Defined Curls for Straight Hair

Even if your hair is naturally straight, you can create defined curls with a thick barrel curling iron for a pin up style.

31. From Pin Up to Starlet

Achieve a glamorous starlet look with well-arranged curls that are both bouncy and natural, perfect for achieving hair goals.

32. Pin Up Rolls Updo

For a bold pin up style, try large bouffant rolls. This dramatic look is a quintessential pin up hairstyle.

33. Vintage and Modern Blend

Combine vintage pin curls with a modern ombre trend, such as bright purple dip-dye, for a unique hairstyle that merges past and present.

34. Rosie the Riveter Inspired Look

Embrace a pin up style with a bit more edge, reminiscent of Rosie the Riveter. This look features black hair with a tougher, more contemporary twist.

35. Intricate Curly Updo

Creating an intricate updo with curls requires patience, but the end result is worth it. Secure and style curls for a detailed pin up look.

36. 1950s Flair

Capture the essence of the 1950s with a high ponytail, bouncy curls, and a headband. This look evokes nostalgia and classic pin up vibes.

37. Headscarf Pin Up Style

Use a headscarf to create a pin up hairstyle with most of your hair covered. Add perfectly curled bangs for a vintage touch.

38. Vintage Style for Short Hair

For short hair, a sleek and neatly styled vintage look requires skill and precision. Seek out a skilled hairstylist to achieve this classic pin up appearance.

39. Volume with V Rolls

Opt for an impressive voluminous roll for a bold pin up style. Crafting a large roll may take effort, but the impact is striking.

40. Modern Color with Retro Curls

Combine retro pin curls with contemporary hair color for a stylish blend. Medium-length hair works well, as it’s manageable and showcases the look.

Pin up hairstyles offer options for every hair type and length. Whether your hair is long, short, or somewhere in between, find a style that highlights your features and complements your look. What’s your favorite pin up hairstyle?