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 skirts 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 pencil skirts have 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 penicl 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 inarguable classic style 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.

This summer, we’re all about the classic high waisted pencil skirt with some modern spins. We’re shaking things up with some eccentric pencil skirts that would make Dior himself proud. From funky prints to chic embellishments, these high-waisted pencil skirts are getting rejuvenated with some contemporary style. So, stitch work-professional and casually chic together with these universal pieces. We promise they’ll make a great fit in your summer rotation.

Are your skirts seeming a little dull? Then sharpen your style with high-waisted pencil skirts.

Athleisure Approach

So apparently pencil skirts and athletic-wear have become one…  Athleisure for many can be seen as a blessing and a curse, on one side of the coin it’s an excuse to throw on your “best” workout clothes in an attempt to get away with looking pulled together by cucking on a blazer or strappy sandals. In the same breath, it’s also the same troubling issue. Whichever side of the coin you prefer there is always one solidifying factor that anything able to alleviate the stress of getting dressed in the morning is a plus on either end of the spectrum. Pencil skirts, in a similar aspect receive the same bad rap, on one side they’re chic, figure-hugging, and more times than not allude to an hourglass-like figure, no complaints there. Stella McCartney enables the racer chick in all of use with the Knit Cotton Pencil Skirt. The navy stockinette-stitched cotton, rib-knit waistband, and red self-stripes make this silhouette flattering on all body types as an inclusive piece that keeps on giving.


Knit Cotton Pencil Skirt

$735 $289

Sequin Stunner

What’s a skirt without a little pizazz, right? Pencil skirts no longer need to be a boring garment that sits in your closet when the “Sunday scaries” kick in and your haunting nightmares of that Monday morning wake-up call comes to life. From the boardroom to the bell of the ball sequins have gone from a formal event to an everyday affair. Sally LaPointe’s Degrade Sequin Pencil Skirt brings out the inner Stunt Queen in all of us. Featured in a neutral colorway that is versatile for any style preference, so dress it up or DRESS IT UP because this one is a stunner just waiting for its debut from the office to the club, or happy hour drinks with coworkers and frenemies alike.


Degrade Sequin Pencil Skirt


Make Do and Mend

Nifty, thrifty design ideas gave way to a chic, elegant, and poised creations made from old men’s clothing. Utilitarian fashion beckons the inclusion of men’s silhouettes, padded blazers synced and belted at the waist, khaki material pencil skirts and tortoise-shell buttons were among many of the notable design elements. Fashion is continuously finding ways to reinvent the wheel, but if it ain’t broke don’t fix it. In recent seasons, the utilitarian aesthetic has found its way from the pages of rationing booklets and onto the runways by the likes of numerous designers from Eudon Choi to Tibi. Max Mara is also making a statement this season with their Dindy skirt mirroring the classic trench style features. The camel-brown silk-organza is a minimalist playground adorned with a high-rise foldover waistband, side slip pockets, and doubled front-button fastenings nostalgic of a 1945 housewife.


Dindy skirt

$1,150 $805

Denim Days

Who here isn’t currently addicted to denim pieces in some form or another, and this Maison Mayle denim pencil skirt just fuels that fire even more. The light-wash denim pencil skirt has a geometric panel construction that gives it a modish breath. Its minimal silhouette-stamped coin charms (which are a signature detail for the brand) adds just a touch of detail without stealing the spotlight, and the skirt sits just over the knee for a style that’s fitting for just about any occasion.


Bibi Denim Pencil Skirt

595$ $359

Pair this skirt with your favorite combat boots for a grungy attitude, or give it a femme appeal with some nude heels. The possibilities are endless.

Suede Persuasion

This knee-length pencil skirt from Escada is everything you need to stay pretty in pink this summer. Its captivating pink-rose hue just screams summertime fine, and the suede material makes it as comfy as it is sexy. This pencil skirt’s banded waist gives your figure a snatched effect and creating an hourglass silhouette that’s both flattering and appealing. This skirt is perfect for any nighttime outing, especially if you’re hitting the hottest club in town.


Laris Suede Pencil Skirt

1,450$ $870

To make the most out of this skirt, try wearing it with a cropped tank top and your favorite stilettos, or dress it down with a cropped graphic tee and a pair of ballet flats.

Greek Inspiration

While nothing says summer more than tanning on the beaches of Mykonos, most of us will find ourselves sitting on the rooftops of Bushwick. So that’s why you need this Versace Collection pencil skirt. It allows you to bask in Greek greatness while running down the streets of New York. The swirling prints are inspired by the Greek god of love, giving this skirt a romantic appeal. These vibrant swirls give the skirt’s base baby-blue color an intriguing effect that will definitely catch some eyes.


Eros Cady Pencil Skirt

525$ $314.98

This is the perfect pencil skirt to wear to the office, and also has enough life to be worn to happy hour. Let this skirt run the show by pairing it with a simple blouse and subtle heels.

So Surreal

Don’t stick to the basic black pencil skirt this summer. Instead, stand out from the crowd by putting on this Maticevski pencil skirt. It’s far from your average black skirt—this piece has an oversized side ruffle detail that gives it a striking and fun spin. It has an surrealist air that would leave even Salvador Dalí stunned, while staying current and vogue.


Intriguing crêpe pencil skirt

1,510$ $1,057

Pair this skirt with a white top for a classic office look with raw attitude, or take your black-on-black style to the next level by wearing your favorite black top.

Horizontal Edge

If you’re more into a conservative style, this knit skirt from BOSS will do just the trick. The white base hue is minimally contrasted by thin black stripes. This skirt makes a major style statement in a minuscule way, and still has all of the figure-hugging power of your average high waisted pencil skirt. If you’re ready to dress to impress, then wear this skirt. It’s a great staple piece for heading to a big meeting and showing everyone who’s the real girl boss.


Knit Pencil Skirt

245$ $147

For a sophisticated style that can’t be beat, pair this pencil skirt with its matching top or keep things low-key with a basic-toned blouse.

Robust Red

To give your summer style some flavor, try out this fiery red pencil skirt from Givenchy. This candy-apple red is great for giving your look some energetic vibes that can’t be topped. Its sheer hemline adds feminine charisma while still staying bold. The elasticized waist gives your body some extra shape and curve, making this your top pick for date night or party.


Knit Pencil Skirt

1,280$ $512

Try wearing this skirt with your favorite black chunky ankle boots and a graphic tee for the ultimate rebellious look.

Chill Vibes

Need a pencil skirt for those relaxed, summer beach days? Then grab this Fendi vertical-lined pencil skirt. This dark blue maxi skirt ends just above the shin, and its dark blue color paired with thin white stripes makes this the staple skirt for any downtown style influencer. Its loose fit gives you the best of both worlds: style and comfort.


Drill Pencil Skirt

1,250$ $750

Tuck your favorite tank into this skirt and stay relaxed with some Birkenstocks for the coolest laidback feel.

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