These 14 handpicked pencil skirts command the sphere between comfort and office style

Where comfort meets style

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Introduced way back in 1954 by none other than Christian Dior himself, the pencil skirt soared to success due to the previous lack of any ‘new’ fashionable designs during WWII. Once the pencil skirt hit the runway, it became quite the icon for the 1950’s era, particularly when paired with back-seamed sheer stockings and heels.

Given their knee length hemline and relatively modest design, pencil skirts have become the epitome of ‘office chic’ and for the stylish ones amongst us, they’re a firm work wardrobe staple.

The only downside? They are rather constricting. Due to the tapered cut, they bind the thighs tightly and this alone can put women off choosing a pencil skirt for her office OOTD – however elegant and feminine they may be.

But, what if we told you that the femininity and comfort are not mutually exclusive concepts – you can have a pencil skirt that is both. WIN.

Click through for our curated handpicked list of the best 15 pencil skirts that are available to buy right now.

Hopsack midi skirt

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“I wanted to create an urban uniform for busy woman who love fashion,” says Samantha Cameron, designer of Cefinn. Made from flexible hopsack, this skirt sits loosely at the waist, allowing breathability.

It ends mid-calf with front and black slits for easier movement and also helps in tempering the slim pencil silhouette. Wear this with a v-neck blouse, tucked in and teamed with pointed stiletto shoes.

Cefinn Hopsack midi skirt, $269 from Net-a-porter

Leaf print skirt

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Cut to sit snugly at the waist, the skirt tapers down with a wrap-effect that allows you to take bigger strides when walking, without compromising on class.

Printed all-over with leaf motifs, we suggest keeping the top simple to not outshine the skirt.

Warehouse leaf print skirt, $38.79 from ASOS

Flocked lace pencil skirt

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Crafted from delicate lace that’s gathered with plush velvet, this cream skirt from DKNY sits at the slimmest part of your waist, offering you a slender frame.

We love the partially lined coverage with a little peek-a-boo of the legs, sexy and stylized all at once. Wear this with an oversized sweater for a more casual look or try on an equally cream blouse for a dressier outfit.

DKNY Flocked lace pencil skirt, $476 from Net-a-porter

Billie lace-up crepe skirt

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The Billie skirt is made from a white crepe that comes fully lined for opacity, making it very suitable for work. But here’s where the fun comes in – a flirty signature front split decorated with silver D-rings and fluttering grosgrain ribbon.

Why not show off the high-waist with a tucked-in top for that sharp office outfit. We say, make it monochrome with a black top and ankle boots.

Rebecca Vallance Billie lace-up crepe skirt, $365 from Net-a-porter

Pencil skirt in stripe with large buckle detail

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We love the wrap-effect, giving you more freedom to move about without all that tapered constriction. Plus, the vertical stripes creates an illusion of a slimmer frame, meaning you totally can reach for that final cupcake during your tedious team lunch meeting.

Pair yours with a ruffled sleeve blouse for corporate vibes or, if you’re in a creative industry, why not rock this with a logo print tee and some mules.

Asos pencil skirt in stripe with large buckle detail, $81.89

Aysha embroidered cotton-canvas skirt

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Elegant and feminine, this structured cotton-canvas skirt from Erdem is beautifully embroidered with colourful Japanese flowers reminisce of a kimono.

Lined in silk-georgette, this skirt boasts of a smooth fit. Style yours with a turtle-neck or collar neck blouse to turn heads in the office.

Erdem Aysha embroidered cotton-canvas skirt, $1,968 from Net-a-porter

Metallic floral-jacquard pencil skirt

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We are in love with the hibiscus pattern that glimmers in gold, against all that rich navy blue jacquard.

The skirt is figure-hugging near the waist, but it loosens up around the thighs to just enough space for easy movement while retaining the snug fit. We recommend wearing this skirt with a neoprene structured box tee.

Prada metallic floral-jacquard pencil skirt ,$1,342 from Net-a-porter

Leather-trimmed wrap-effect wool pencil skirt

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The ultimate comfort you can ever find in a pencil skirt, Max Mara’s leather-trimmed pencil skirt allows you to move freely with its flattering wrap-effect detail.

Knitted from mid-weight wool, finished with soft leather pockets and a smooth waistband that hangs loosely, pair it with a soft beige camisole for the office.

Max Mara leather-trimmed wrap-effect wool pencil skirt, $771 from Net-a-porter

Suedette pencil skirt with tie detail

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Made from a beige suedette, NaaNaa’s pencil skirt with tie detail will be your go-to skirt whenever you’re pressed for time…but be sure to pair it with a modest top as the high slit can be somewhat revealing for certain office environments.

Team with a simple round neck t-shirt plus a blazer and you’re ready for work.

NaaNaa sudette pencil skirt with tie detail, $68.96 from ASOS

Floral-print silk-blend charmeuse midi skirt

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Very feminine and ‘ladies who lunch’, Dolce & Gabbana’s silk-blend charmeuse skirt is figure-skimming and patterned with lush hydrangeas.

All attention will be on the skirt, so we suggest pairing this with a plain blouse to complement all that floral action. We also suggest wearing it on an actual lunch…away from your desk (you need breaks too you know).

Dolce & Gabbana floral-print silk-blend charmeuse midi skirt, $1,268 from Net-a-porter

Houndstooth wool pencil skirt

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We love the pink and white houndstooth pattern – a refreshing change from the usual monochromatic theme.

Paneled at the sides to create a slimming effect, the satin lining and back vent ensures a smooth and comfortable fit. Team yours up with a black oversized top slightly tucked in for that punchier look.

Prada Houndstooth wool pencil skirt, $1,252 from Net-a-porter

Bow-embellished cloque midi skirt

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Dainty and stylized, Fendi’s pencil skirt is crafted from tactile cloque blend with touches of silk and a thigh slit. We love the playful row of grosgrain bows right above the slit, giving a flirtatious charm to the skirt.

This detail makes this skirt a perfect option for any after-work activities – it is versatile enough to extend to an evening occasion. Tuck a white v-neck shift blouse with this during the day, then just swap for a sweetheart neckline tube top for your evening antics. Sorted!

Fendi Bow-embellished cloque midi skirt, $1,325 from Net-a-porter

Silaas pencil skirt

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Ted Baker’s Silaas pencil skirt is flattering for the frame, while the solid white colour allows for it to be easily paired with any top.

Versatile and chic, team yours up with a one-shoulder cropped top for a more feminine charm.

Ted Baker Silaas pencil skirt, $301.70 from ASOS

Bugia stretch-wool pencil skirt

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Keep your outfit fresh with this soft pink Bugia pencil skirt from Max Mara. Made from stretch-wool and fully lined in satin, each panel is subtly detailed with zigzag topstitching and flattering pleats at the back.

This helps to balance the hips and creates a little graceful sway with every step. Wear yours with a bow detailed blouse.

Max Mara Bugia stretch-wool pencil skirt, $540 from Net-a-porter

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14 pencil skirts for the office that balances style with comfort

There’s no need to sacrifice your style (your sanity, maybe) when it comes to those long days at the office

Privacy Menu

S / Shopping

14 pencil skirts for the office that balances style with comfort

There’s no need to sacrifice your style (your sanity, maybe) when it comes to those long days at the office

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