The History Of The Pencil Dress – From Pilots to Pop Culture


The pencil dress is a timeless piece and a staple for every wardrobe.

Flattering and modest, yet with a slight edge, pencil dresses are a wonderful creation.

They’re incredibly versatile and can be worn almost anywhere.

Although, they’re probably not the best for marathon running.

All jokes aside, this iconic shape also has a rich history, falling back all the way to the first female flight passengers in 1908.

Pilots And Parisians

When the Wright brothers sent the first female passenger on a flight in 1908, they noticed that the long, flowing cut of her dress would pose a fair problem in the high winds of flight.

The passenger (named Mrs. Berg) would not be able to keep her outfit in check at all- unless they tied something around her ankles, perhaps?

This is exactly what they did.

Thus, the eye-catching pencil shape was born from a piece of rope and some pesky wind.

This flight became infamous, and Parisian designers soon took interest in the unique shape of the skirt in question.

This became known as the ‘hobble skirt’.

Soon enough, the fashionable ladies of Paris were all hobbling around merrily.

Prior DiorWoman wearing a blue, floral print pencil dress and heels

After the Parisian fad of hobble skirts, the need for beautifully styled skirts died down as the 20s came in with war-time demands for less material and more practicality.

The next key point in history that the beautiful pencil shape came into fashion was in Christian Dior’s H-Line collection, in 1954.

This collection was the stuff of fashion legend.

Unlike typical A-line cuts which emphasized waistlines, this collection highlighted the wearer’s hips and encouraged more parallel lines in outfits.

There are so many gorgeous pieces to discuss from this collection- beautiful, boxy Bar suits, and fabulous formal dresses.

However, the most iconic introduction here is still the pencil shape.

This new idea of how to wear skirts and suits revolutionized fashion and sent Paris and its glamorous inhabitants reeling in shock.

Pin Ups

Dior certainly started a trend, and it was leaped upon eagerly by the starlets of the 50s.

The gorgeous Betty Page was known for wearing this style, and Marilyn Monroe was no stranger to it either.

There is an infamous scene where Monroe is wearing a pencil-cut skirt, strutting past her co-stars at the train station in the film Some Like It Hot.

This is one of the first times the pencil shape has been seen in popular media, and it definitely left an impression on the public.

Princess Grace Kelly also enjoyed wearing this iconic style of dress and skirt, inspiring awe with her classic yet stunning looks.

The green pencil skirt suit that she wears in the film Rear Window is often cited as one of the most iconic movies looks from that era.

Possibly the most well-known example of a pencil dress on a well-known movie star is Audrey Hepburn’s little black dress in Breakfast At Tiffany’s.

There is a reason that this outfit is replicated so often- it is instantly recognizable and absolutely classic.

To this day, fashion inspiration can still be drawn from this outfit.

Woman wearing a red pencil dress and heels near a window with curtains

Pop Idols And Pretty Patterns

Throughout the next few decades, the pencil dress changed in length, textures, colors and more.

The 60s added a new, daring twist to the cut by simply making it shorter.

Influential designers such as John Bates and Mary Quant adored this look, and this can be seen by looking back at their unique collections.

The pencil dress wasn’t as popular during the 70s- perhaps it wasn’t flared enough? It roared back to life in the 80s, however.

Stylish fans of this cut paired it with bright, padded jackets and unique jewelry for a truly eye-popping look.

Even Madonna was known to wear this style on stage during her concerts.

Pencil dresses and skirts can also be found in Vogue, showing the adoration the fashion world had for this statement look.

The 90s added new patterns and textures to the pencil cut, making the look edgy in the way only 90s fashion can.

Tartan, animal print and distressed material were all staple ingredients for a successful pencil dress look.

To try this look out yourself, pair a patterned pencil dress with chunky boots, fishnets and an oversized hat to channel your inner Courtney Love.

When the Millenium hit, textures in fashion were everything.

PVC and latex were new, daring mediums to experiment with, and these translated well to pencil dresses and skirts.

Lady GaGa was spotted in the press showcasing a blushing pink latex pencil skirt and a black bralette, highlighting her individual, quirky style.

Pencil dresses and skirts were also seen popping up on catwalks, experimenting with embroidery and embellishment to liven up a classic look.

Present Day

Woman wearing a pink and navy blue pencil dress by a blue background

To this day, the pencil dress is still an absolute classic.

It is a staple for powerful, working women, but is also being revolutionized once again by forward-thinking fashion lovers.

If you’re a fashion fan, you’ve probably seen women experimenting with dressing the pencil cut for day and night wear.

It can still be found on catwalks, but also in high street stores.

For a daytime look, pencil dresses can be worn with oversized knitwear and comfortable sneakers to create a casual vibe.

Drawing inspiration from the 80s trend of statement jewelry would work wonderfully here- try a chunky, colorful necklace or a few eye-catching bangles.

Alternatively, this look can be styled for the office with a simple jacket and a pair of neutral pumps.

The pencil dress can be styled for night time as well, especially for formal events.

To really glam up your outfit, channel your inner Audrey Hepburn and go for a sleek, all black gown.

Pair with simple silver jewelry, a glamorous shawl and heels, and you’re good to go.

If you’re hoping to go somewhere more casual in the night, try a pencil skirt instead.

Complete your look with a graphic t-shirt, leather jacket and platform heels for an edgy, alternative vibe.

If you’re still wondering whether to try out this look or not, think about the history behind it and how many beautiful women have worn it.

There’s a pencil dress for everyone!

Just choose a good quality material and a color that suits your complexion.

Then you’ll be sure to have a killer look.