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If you’ve ever seen the first episode of Mad Men you might recall the scene where Pete tells Peggy she has cute ankles and she should make them sing — in one of the sexy pencil skirts the other secretaries wear. "How dare he! She should not have to wear a newfangled sexy pencil skirt if she does not want to!" You might have thought. If you’ve not seen that scene, you probably think of pencil skirts as the skirts that you buy off Modcloth that your Grandma really approves of.
But they actually do have a pretty sexy history, beginning in 1908 with the first female passenger on an airplane. When Wilbur and Orville Wright brought Edith Berg onto their brand new plane, they were worried that her long skirt might get caught on the machinery. So they tied a cord around her skirt slightly below her knees to help hem it in. When she stepped off the plane she was photographed wildly (it was a big deal! She was the first woman on the plane!) and the hobble skirt was born. The hobble skirt was a traditional long skirt that was tied around the legs below the knee, created an effect similar to the pencil skirt, if the pencil skirt had a long ruffle poking out beneath it. You can see a picture from of it from the 1910’s here.
By the 1940’s, Christian Dior decided to do away with that excess ruffle and the pencil skirt was born. However, his pencil skirts really took off in 1954 with his H-Line collection. Immediately after World War II Dior had become famous for his New Look, which featured dresses with huge ruffled skirts and tiny cinched waists. The popularity of that look had a lot to do with the post-war economic boom and the end of rationing, which meant that people could get clothes with tons and tons of fabric in them. Some of the New Look skirts were meant to be paired with a crinoline to make them even wider and more billowing. The popularity of the H-Line and the pencil skirt had to do with people getting really sick of the New Look. Women who’d been wearing overalls through the war realized that wearing a ballgown everywhere was not necessarily as fun as it might have initially seemed. The new pencil skirts allowed women to show off their feminine curves, and not be quite as impeded from going about the business of daily life as they would have been in the immediate post wartime fashions.
I should stress the not quite as impeded part, though. The original design for pencil skirts was meant to cling to a woman’s body so tightly that some women had difficulty walking in them, especially if the skirts went over the knee. The slits you see in the back of pencil skirts weren’t just to add a cool little extra glimpse of leg. They were a practical necessity that meant women could stretch their legs out enough to walk. The dance the Twist became popular around 1960 after Chubby Checker demonstrated it on the Dick Clark show. Partly, that’s doubtless because the Twist — which just involves swiveling your hips back and forth — is a fun dance. But part of its popularity was also due to the fact that, given the fact that they couldn’t kick their legs out or take very large steps, it was the easiest dance for women in pencil skirts to do.
Fortunately, the skirts got a bit looser as time went on. And, at first, well, at least you didn’t have to strap yourself into a crinoline before you headed outside.
Imperfect though they might have been from a practical standpoint, a lot of celebrities really embraced the opportunity to show off their curves in pencil skirts. Pencil skirts became a staple of Marilyn Monroe’s wardrobe prompting Jack Lemon to exclaim "Look at how she moves!" when she wore one in Some Like It Hot. Cool fact — Marilyn Monroe’s wiggly walk was actually due to the fact that one of her legs is said to have been shorter than the other. Or because pencil skirts are sexy and they make you walk like a sexy lady! I don’t know, probably the former, maybe the latter.
Once Marilyn was doing it, plenty of other stars known for their sex appeal starting wearing the new skirts. You’ll see them on celebrities like Elizabeth Taylor, Grace Kelly, and Betty Brosmer (a largely forgotten but gorgeous model). Even ladylike Audrey Hepburn got in on the trend when she played a call girl in Breakfast at Tiffany’s.
The notion conveyed was that the pencil skirt was an item for the sexually confident and sophisticated woman. Teenagers were told not to wear pencil skirts on account of how it would probably turn them into uncontrollable sex sirens. Teenagers ignored that advice and wore tons of pencil skirts, because that’s what happens when you tell teenagers they’re too young to do something.
By the end of the 1960’s, however, pencil skirts began to seem dated. Teenagers who wanted to be sexy sirens would adopt mini-skirts instead. Some claim that miniskirts were merely a natural shorter evolution of pencil skirts, but that is a lie. They’re a different thing that you can definitely kick your legs out in. That said, pencil skirts never really went away, and today they’re a staple for office workers — and thank God, they’re a little easier to walk in than their original incarnation. You’ll see them on celebrities today like Kim Kardashian and Angelina Jolie, and they look just as curvy and great in them as Marilyn Monroe did 50 years ago. Pete Campbell would be so delighted.