This Exact Kind of Midi Skirt Is the Most Flattering Item You’ll Ever Own

I know, pencil skirts aren't exactly the most comfortable of items. They’re often thought of as stuffy and uncomfortable. Tugging and readjusting your skirt isn't exactly chic. That said, the working women among us rely on the fact that the pencil skirt is an essential when it comes to a professional wardrobe, right alongside a tailored suit and a closet full of button-down shirts. Long story short? The pencil skirt is going nowhere. As such, stylish women are reinventing cool new ways to wear one that has us giving the garment a second glance.

The high waist and tailored shape have long established this piece as a go-to figure-flattering option. Right now, we’re loving the way street stylers are making a pencil skirt feel fresh again with cool leather finishes, new deconstructed silhouettes, and off-duty styling (aka a graphic tee and sneakers). We never thought we’d say it, but we’re totally feeling a newfound romance for the professional mid-length skirt.

Read on to see how to wear a pencil skirt like these stylish women and shop the coolest ones out there.

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(Image credit: Getty)

Style Notes: There's something about a matching skirt and jacket that can feel a bit too Working Girl. However, to avoid any fancy dress comparisons, it's a good idea to add a pair of socks and sandals to make it way more interesting. 

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(Image credit: Getty)

Style Notes: This might be a bit chilly for the colder months but if you want a great wedding guest outfit for the spring, then this is it. You can always wear a checked pencil skirt with a pair of sneakers, a tee and big coat. 

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Style Notes: There's nothing we love more right now than a bit of feather embellishment. Prada has us lusting after this skirt. 

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Style Notes: A super cool way to do the pencil skirt is to layer with an oversized white shirt. Wear a roll neck underneath as well as a pair of ankle boots and you've got a fail-safe winter outfit. 

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Style Notes: Lisa Aiken's take on the pencil skirt is decidedly more sassy, which we totally love. Go for one with a split up the middle and pair with a form-fitting top. It feels modest but still revealing. 

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(Image credit: Collage Vintage)

Style Notes: Gloss it up in a vinyl or patent finish à la Christine Centenera. Good news: These pencil skirt iterations are all over the high street now too. 

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(Image credit: Collage Vintage)

Style Notes: Tuck a cosy sweater into a patterned skirt and you've got yourself the ideal fall workday outfit.

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(Image credit: Collage Vintage)

Style Notes: A must-try combination: gray checks and bright red. 

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(Image credit: Style du Monde)

Style Notes: Just add a statement top and statement earrings to make a grey skirt more interesting. 

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(Image credit: Style du Monde)

Style Notes: Leopard print and a graphic tee always go so well together.

Shop our favourite pencil skirts:

Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.