Pin Up Dresses Through the Decades: Vintage Fashion

Introduction

Few fashion icons are as enduring as the pin up girl. With her bold curves, flirty poses, and show-stopping wardrobe, she’s influenced everything from red carpet style to everyday vintage looks. And at the center of her look? The pin up dress—timeless, tailored, and endlessly iconic.

In this blog, we explore the history of pin up dresses through the decades and how they continue to inspire modern pinup portraits and fashionistas around the world.

The 1940s: Practical Yet Glamorous

During WWII, women’s fashion leaned toward functionality—but that didn’t mean giving up style. Pin up girls of the era often wore:

• Halter dresses with sweetheart necklines

• Modest hemlines with flattering waists

• Patriotic colors and military-inspired trims

These styles reflected resilience and femininity during wartime, often seen in WW2 pinups and vintage posters that boosted morale for troops.

The 1950s: Full Skirts & Bold Statements

The golden age of the 1950 pin up model introduced:

• Full swing skirts and cinched waists

• Bold prints like polka dots, cherries, and gingham

• Off-shoulder sleeves and sweetheart bodices

• Crinolines for extra volume and flair

These styles highlighted the hourglass figure and are still favored in modern pin up photography and vintage pinup portraits.

The 1960s–1980s: Evolution and Edginess

As fashion evolved, so did pinup style. Though less mainstream, retro influences stayed alive through:

• Pencil skirts and fitted wiggle dresses

• Rockabilly edge with leopard prints and leather

• Tattoos and pin up female empowerment through alternative modeling

This era birthed the tattooed pin up girl tattoo look, combining vintage fashion with modern ink and attitude.

Today’s Pin Up Style: Mix & Match

Modern pin up girls blend the best of every era with a twist. Today’s popular styles include:

• Vintage-inspired swing dresses

• Curve-hugging wiggle dresses

• Corsets and retro lingerie sets

• Custom-tailored dresses for any body shape

You’ll find these looks in photo shoots, pinup parties, burlesque shows, and of course—custom pinup art.

Pin Up Dresses in Digital Portraits

At Pinup Portrait, we let you choose your outfit! Whether you want:

• A sweet polka dot dress from the 1950s

• A sailor-style halter dress from WWII

• A modern twist with tattoos and bold heels
  —we’ll digitally create a look that flatters you while staying true to the pinup tradition.

Choosing the Right Dress for Your Portrait

Not sure what to wear in your custom pin up portrait? Our artists help you decide what works best for your body, pose, and personality. Plus, no need to shop for a real dress—we’ll dress you up in digital style!

Conclusion

From the battlefield to the photo booth, pin up dresses have stood the test of time. Their flattering cuts and vintage glamour continue to inspire women of all ages—and now, with custom portraits, you can wear them in digital art that celebrates you.

Call to Action

Ready to step into vintage style with your dream dress?
👉 Order your custom pin up portrait today and let us dress you in timeless fashion—no wardrobe needed.

Frequently Asked Questions

What is pin up style fashion?
It includes high-waisted skirts, vintage dresses, bold red lips, and glamorous pin up hairstyles from the 40s–50s.

How can I get classic pin up hair?
Victory rolls, curls, and bandanas are signature looks — tutorials are available or you can request them in your portrait.

Can I dress like a pinup for my photoshoot?
Yes! Choose outfits that highlight curves, add bold makeup, and strike a confident retro pose.