How To Dress Pin-Up Style [With A Tutorial]

In love with the 1940’s fashion? The pin up girl is an icon of the 1940’s.

How To Dress Pin-up Style [With A Tutorial]

The pin-up girl aesthetic has endured through the ages thanks to its timeless designs and seductively charming appeal.  

Want to try it out but not sure where to start? Below we cover what you need to dress pin-up style.

From the fitting pencil skirt to the flirtatious stockings, you can show your true self through this iconic vintage style. 

All you need is to read below and have confidence for all of the states of wonder you are going to receive!

What Is Pin-Up Style?

Before we get into the ins and outs of how to dress in the pin-up style, it is important to know what it is and what it represents. 

As men were shipped off to war in the 1940’s, women became the backbone of the workforce.

Allowing women to explore more freedom with their dress sense, makeup looks, and hair styles. 

The pin up style was hugely popular among models, burlesque performers and eventually the everyday women. 

The pin-up style was loved so intensely by women all over the world that it even made its way into the 1950’s.

In this time it began to merge itself with Hollywood and became a symbol for the rock ‘n’ roll lifestyle of glamor. 

Essentially a pin-up sense of fashion represents women taking control of their independence.

Much like the Flapper Girl style did in the 1920’s.

The pin-up can be seen throughout time as being elegant and classy with a sense of sensual and alluring. 

Pin-Up Style Essentials

When beginning your journey into the world of pin-up fashions there are a few staples you are going to need.

These are items that you can wear in multiple ways to create gorgeous outfits that will encapsulate your daring, sensual side. 

A Pencil Skirt 

A pencil skirt is more so worn at the office in today’s fashion.

However, a pencil skirt is perfect for providing your pin-up wardrobe with more range. 

A well-fitted pencil skirt will outline your feminine features such as your hips and bottom while remaining conservative with the long hem line. 

Your pencil skirt should be bright and eye-catching to achieve a traditional pin-up look or keep things more gothic and subdued with a black skirt.

Either way this sultry piece of clothing is sure to make you feel like a confident woman. 

A Circle Skirt 

A tight fit is not pleasant for everyone. Circle skirts were a mainstay of the pin-up look in the 1950s.

Due to their straightforward design, they’re nicknamed circle skirts! 

Simply cut out a circle of fabric with a smaller circle in the center.

the smaller circle will serve as your waist and the larger circle will serve as your hem to create one.

Cigarette Trousers

You may remember cigarette trousers being widely popular throughout the 2010s.

With everyone from young girls to working women seeking the stunning fit of these trousers, it is no wonder they find themselves in and out of the fashion trends. 

These pants give you an hourglass look by drawing your waist in and hugging your hips; they then cut off stylishly right above the ankle.

High-Waisted Shorts

Throughout Spring and Summer you may find the high-waisted shorts a saving grace.

Tight at the waist and wider at the thighs provides the illusion of a smaller waist with wider hips. Perfect for a pin-up silhouette.

How To Dress Pin-up Style [With A Tutorial]

Take your high waisted short outfit up a notch and pair with a flirtatious pair of stockings for an even more daring look. 

A Cardigan/Sweater

As the main body of pin-up outfits are rather tight fitting, adding a waist-line cardigan can add just a touch of movement. 

A cardigan is certain to add the finishing touch to your ensemble whether you wear it over it, on its own as a top, or tucked into the hem of your skirt.

A Wriggle Dress

The wriggle dress is one of the most iconic items of clothing when it comes to the pin-up style.

It is form fitting with a ruching section in the middle.

This allows the dress to highlight your natural figure and show off those curves. 

This has become the pencil dress of modern times but it is an essential item of any pin up wardrobe. 


If you find changing your entire wardrobe a bit too daunting, why not try adding a simple pair of stockings. 

In order to highlight your legs in pin-up style, you must wear a pair of stockings that emphasize your pins.

Picking tights or stockings with suspenders will definitely modernize your attire, but choosing seamed stockings with the line running up the back of the leg will give you a genuine 1940s style.

Pin-Up Outfit Tutorial 

Once you have looked out all of your favorite clothing items that best fit the pin-up style, you might be stuck on what to do with them.

Do you just try them on and hope for the best? 

Assembling a pin-up outfit can take a little bit of work if you don’t have the know how.

That’s why we have included this simple video tutorial to ensure that you have a simple pin-up look that you can wear every day. 

There is also no need to go out and purchase new items.

You are sure to find something in your current closet that gives you the sensuality of a pin-up model. 

Final Thoughts 

No matter your size, shape or style, you can find a way to incorporate the pin-up style into your everyday looks. 

With a simple pair of stockings and a form fitting skirt you can create a figure hugging outfit that shows off those womanly curves and brings your confidence. 

Take a look at the pin-up style essentials above and find items in your closet.

Then follow the video tutorial and create your own classic, seductive look that you feel confident and powerful in. 

Willa Price