Vintage Skirts | Rockabilly Pencil Skirt | 50s Skirt

27th August 2020

The 50s rockabilly pencil skirt and how to style it

rizzo | How to style vintage pencil skirts

Pouring over old pictures, vintage pencil skirts are the cornerstone of 50s rockabilly style. The humble pencil skirt is a staple in any wardrobe and even more of a key item in any vintage look, particularly those of you who have a rockabilly or pin-up flair to your style.

The history of pencil skirts & who designed the first one

It’s claimed that the pencil skirt originated in 1908 when a lady called Edith Berg boarded a plane with a wide, flowy skirt. Allegedly, her male companions were worried that her long skirt might get caught on the machinery. So, what did they do? They tied a cord around her ankles to help keep her skirt from flowing around. Very creative, we must say…

And then came the “Hobble Skirt”, which is the pencil skirt’s short-lived older sister. You may be thinking, why is it called a hobble skirt? Well, you may be shocked to hear, they were called hobble skirts because… they made you hobble. Due to being so tight below the knee, the hobble skirt didn’t allow for a broad range of motion.

Christian Dior was the first known designer to introduce what we now know as the classic pencil skirt in his 1954 H-line Autumn collection. And this is when we saw icons like Marilyn Monroe, who is arguably one of the biggest trend-setters from the 50’s, wearing the humble pencil skirt. Though we do see some similar styles in earlier years, mainly during the Flapper era, but they were slightly less form fitting.

HobbleSkirtPostcard | How to style vintage pencil skirts

So if you love the look of vintage pencil skirts but you don’t know how to style them…

We’ve got you covered.

If your style is more Bad Girl, or if you’re devoted to Dita’s style, maybe even besotted with Betty Page… Is it that Jayne Mansfield wiggle you’re looking to create, or do you just wanna have fun like Rizzo? To nail the look you need to have a great pencil skirt or 3 in your clothing arsenal.

Here’s our breakdown of how to style a pencil skirt & when we’d wear it

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The main star of the show here being our V2 pencil skirt, which is cut with rear darts & zip.

The front darts are cleverly hidden within the cut of the pockets. Yes, that’s right, these babies have pockets. Skirts with pockets rule & I mean, while they’re not big enough to carry your whole life around, you can keep your keys, phone & card right on you without needing a bag.

Made with stretch to move when you do, our V2 comes in simple block colours so they can work effectively throughout your wardrobe with all of your tops.


So, if you’re looking for a new stylish yet comfortable outfit that gives you the perfect rockabillies style, we’ve got you.

If 50s rockabilly fashion is more your style..

We’re talking Rizzo from Grease, and her classic badgirl look which is 100% sassy and 100% gorgeous. You know that full black ensemble where she just looks badass? Yeah. We’re obsessed with it! And we’re getting major sweetheart style inspo from Marty. We adore how she matches her accessories to her pencil skirt. Such a simple but effective idea – and you probably have some fabric lying around somewhere that you can use as a neck tie, so you can repurpose old unused fabric AND channel your inner Marty at the same time… um, yes!

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To recreate the iconic Rizzo outfit, pair our classic vintage V2 pencil skirt with our Priscilla top which is a fitted shirt with turned up sleeves & a collar for that true rockabilly look. Add a wide belt to sinch in your waist and throw on a denim or leather jacket for extra brownie points!

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If a more low-key modern vintage look tickles your fancy a bit more…

This look is going to be perfect for brunch with your friends, gigs, or just a casual sunny day.

Pair our V2 pencil skirt with one of our rockabillie inspired graphic tees or our Cher top. Why not channel your inner Ann Margret and go with one of our leopard print tops!

We adore this Barbie look by Miss Sweet Black. So fun! And our pink V2 skirt is perfect for it.

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Something for date night perhaps? But let’s make it pin-up!

Whether it’s a date with your boo or a date with your girl gang, a halterneck or fancy top transforms a range of vintage skirts from comfy casual day time to a perfect cocktail ready outfit.

Pair our Tabatha halterneck with our V2 skirt for that sweet but sexy look, like Jasmine has here. Add a pair of heels if that’s your thing, and get ready to strut your stuff!

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How have you worn yours? We’d love to see the looks you create with your vintage style skirts from Lady K Loves. Tag us on Facebook or Instagram. Why not leave a review too & help the community get the right size & fit.

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