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Pencil Skirts (And The Way You Wear Them) Don’t Have To Be Boring

Take cues from the coolest girls on the streets, then shop our edit of corporate-cool skirts that will take you through the whole work year.
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When you think pencil skirts, you think white shirt, pumps and then end of story. Contrary to the images that it conjures of not-so-sexy librarians in orthopaedic shoes, the pencil skirt is possibly one of the most flattering things you can own – if you pick the right fit. And, if you avoid the whole courtroom student aesthetic. Slit or no slit, the pencil skirt that fits like a glove says business while fanning the flames of femininity and formidable femme fatale. How’s that for an alliteration?

In our continuing efforts to help you start the new year (and work year) on a fresh slate, we’re zooming in on the office wear staple – the pencil skirt. As always, the best place to look at how a certain simple wardrobe piece can be spun into something unquestionably cool is to look at the streets of the many fashion weeks. Everyone’s favourite runway.

The simplest way to kick up street cred with a pencil skirt is to layer it over over-the-knee boots. There’s just something extremely alluring yet badass about that continuous line that shoes no skin. Turtlenecks in a variety of colours are It girl ammo, but you adding an oversized shirt over doubles both the corporate and cool factor. (If you want to see how one pencil skirt can be worked in a variety of ways, look no further than Teddy Quinlivan.)

On Dressed Down Fridays, don’t be so quick to reach for those worn-out jeans. Keep the t-shirt and hoodies, then throw in things like oversized belts or sneakers. The ultimate office-meets-weekend remix. Finally, remember that there is more than one kind of pencil skirt. Balenciaga and the new Calvin Klein under Raf Simons may have proved that the classic over-the-knee straight-cut needs no fixing, but you’re entitled to options. Ruffles, tie-waists, patent, cargo pockets, slits, knits and tassels.


Altuzarra Embellished Silk Satin-Trimmed Crepe Skirt


Balenciaga Wrap Slit Skirt


Burberry Knitted Midi Skirt


Calvin Klein 205W39NYC Striped Cady Midi Skirt


Calvin Klein 205W39NYC Houndstooth Wool Midi Skirt


Marco de Vincenzo Ruffle-Trimmed Satin Pencil Skirt


Oscar de le Renta Fringed Checked Cotton-Blend Tweed Skirt


Palmer//Harding Tie-Waist Cotton Wrap Skirt


Saloni Patent Leather Pencil Skirt


Silvia Tcherassi Belted Gingham Cotton-Blend Pencil Skirt

What To Read Next: Our Best Places To Shop For Basics, From $5 To $500, How To Transform Your Work Wardrobe In An Instant (Well, Almost) and 9 Outfit Colour Combos You’ve Never Tried But Now Wish You Did | Cover Image: YOYOKULALA.com, with images by Sandra Semburg, Jonathan Daniel Pryce and Phil Oh 

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