How We’re Styling Pencil Skirts This Fall

As we get ready for fall, one thing we can’t get enough of is the classic high waisted pencil skirt with some modern spins. Nothing lets out our inner girl bosses more than the pencil skirt. This work-approved piece lets us add just a dash of sultriness to our everyday office attire. Plus, it’s a perfect way to transition your daytime style into a sexy post-shift look.


The slim-fit style of pencil skirt makes them a playful (and tasteful) way for office fashionistas around the globe to express their sartorial edge while staying professionally polished. At the same time, pencil skirts are versatile enough to wear to any casual occasion without suffering from the dreaded sense of over dressing, so  don’t think for a minute that this slender skirt is made to sit under a desk all day.


Although it seems like the pencil skirt has been around since time itself, it’s actually pretty new in comparison to the LBD and other timeless wardrobe staples. The pencil skirt was first created by none other than Christian Dior back in 1954 as part of his H-Line collection. Similarly to the concept behind his creation of the A-line skirt, the H-line was named after the silhouette this piece created with its parallel-lined structure. Dior’s fresh concept on the skirts of this era shifted the focus from the waist to the hip. He did so by tailoring the skirt to curve over the hip and narrow towards the knee, creating a more voluptuous figure. Its form-fitting shape also stood out in its fit, which added a bit of sex appeal to its wearer’s stride. Think Joan Holloway in Mad Menoffice secretaries around the globe had never felt more sexier, and it was all thanks to the revolutionary pencil skirt.


Since its conception, the pencil skirt has seen various recreations of hemline, material, and design. Dior’s initial pencil skirt makeup was drastically altered in the 1970s when designers started using Lycra to render their iterations. Even now, quite a majority of pencil skirts we see on both working girls on Madison Ave and downtown it-girls are made of the stretchy, form-hugging material. However, there are still plenty of options for pencil skirts made from a variety of fabrics, including comfortable cottons and luxurious silks.


While there are many low-rise pencil skirts, the inarguably classic pencil skirt is high-waisted. Dior’s first pencil skirt was high waisted, so who are we to mess with the king of fashion’s vision? Still, that doesn’t mean this classic fit doesn’t deserve a modern refresher. With the new season coming up, we’re emptying out our wardrobes and stocking them with some exhilarating takes on the standard fit.


We’re shaking things up this fall with some eclectic pencil skirts that would make Dior himself proud.


Our top pencil skirt picks this season:


The pencil skirt to wear to work: Misook Tweed Knit Pencil Skirt

How to Make a Pencil Skirt Work For Just About Everything

Most people opt for a simple black pencil skirt for a workplace outfit. But black can get boring. The reason we turn towards the simple black look with our professional pencil skirts is because it is a classic. But keep in mind that black is not the only classic. This fall, opt for a tweed look for work. Tweed is just as classic, if not more, dating back to Chanel’s revolutionary tweed skirt suit number. This style by Misook is done in a dark gray color with a sleek contrasting waistband. For a fall workwear look, pair this pencil skirt with a maroon sweater and nude pumps.



Classic V-Neck Sweater

$550 $175.69


Tweed Knit Pencil Skirt



Wide Fit Paris pointed high heels - Beige



The pencil skirt for a casual daytime look: Nobody Denim Siren Skirt Natural in White

How to Make a Pencil Skirt Work For Just About Everything 1

Can’t mess with the classics. A denim skirt never goes out of style as a timeless piece every woman should covet in their wardrobe, and a denim pencil skirt fits the bill. The denim obsession continues to hold near and dear dating back to the 19th century, later popularized during the mid-1950s with the likes of James Dean and Marilyn Monroe. As the saying goes, the rest is history as brands such as Levi Strauss and 7 For All Mankind have capitalized on the stapled item. From denim jackets to jeans this versatile textile is transformative including that of a high-waist pencil skirt. Try an alternative twist with Nobody Denim’s white denim skirt, perfect for fall. Pair this skirt with cable knit sweater and a classic pair of Chelsea boots.



Cable Knit Sweater



Siren Skirt Natural - White



Moscow Chelsea Boot, Size 9.5 M - Brown



The pencil skirt for dinner and drinks: Costarellos Velvet Pencil Skirt

How to Make a Pencil Skirt Work For Just About Everything 2

Velvet is the quintessential cool-meets-dressy casual look. It is an elegant material but also very on-trend this season. This velvet number by Costarellos is a fantastic pencil skirt for fall, not only because of its classic fit and form. Its knee-length hem with a back split and a back zip allow for an easy wear, and with a 100% cotton makeup, you know this skirt will feel comfortable. But what makes this skirt absolutely perfect for fall is its deep, rich mauve coloring. The color is just what you need for any fall plans. Wear this skirt for a casual dinner and drinks evening alongside a long sleeve button down top and cute ballet flats.



Button Down Shirt - Black



Velvet Pencil Skirt



'Carson' Ballet Flat, Size 8.5 M - Black



The pencil skirt for a night out: Milly Jami Sequined Pencil Skirt

How to Make a Pencil Skirt Work For Just About Everything 3

A little party never killed nobody— (insert Great Gatsby quote here). The 1920s or the “roaring-twenties” as it was often referenced was the birth of the modern world. The age of speakeasies and prohibition, industrialization and wealth, flappers and all that jazz. The style of choice followed It-girl Clara Bow the quintessential flapper type. Flappers were young women who wore short skirts, bobbed hair, bee-stung lipstick, and often danced to jazz music in speakeasies flaunting their disdain for what was then considered acceptable behavior. Women were promiscuous, daring, and in-tune with their sexuality as they shuffled passed in their sequin and fringe ensembles. Unleash your inner flapper with the Milly knee-length sequin pencil skirt. Shake and shimmy your way to a jazz bar near you or paint the town red asking for a Gun Rickey on the rocks — shaken, not stirred.



V-Neck Sheer-Sleeve Sweater



Jami Sequined Pencil Skirt



Kamilli Kitten Heels



The pencil skirt for a daytime party: Akris Jacquard Pencil Skirt

How to Make a Pencil Skirt Work For Just About Everything 4

When you look at this cotton jacquard skirt by Akris, the word “casual” does not immediately come to mind. Typically, a jacquard pencil skirt is best worn with a matching blazer and sent to work for a stylish professional outfit. But when paired correctly, a jacquard skirt is just what you need for a casual daytime party. Our suggestion? Wear this skirt with a simple white blouse and heeled ankle boots.



Central Blouse



Jacquard Pencil Skirt

$395 $158


heeled ankle boot in snake print - Multi



Photo: Shutterstock

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