Not All Shoes Go With Pencil Skirts, But These 5 Definitely Do

It's official: pencil skirts are back. After retreating out of the limelight for the past few years, the sexy style is back on the hips of those in the know. Unlike its '00s ancestors, 2024's pencil skirts look undeniably fresh. Void of bookish, stuffy or drab connotations, this season's iterations utilise all of the learnings of yesteryear to create figure-hugging styles that top the charts for class, elegance and style. Ushered in by the resurgence of the '90s and Y2K, the trend, which was formally the reserve of the office, has looped back, bringing with it fishnet tights and sharp kitten heels.

You might remember from the first time around that the skin-tight skirt isn't the easiest to style. Trickier than a flowing maxi or a cute mini, a fitted pencil skirt looks amazing with certain shoe styles and less captivating with others. I've done the hard work for you and figured out how to make it work, so to get your inspiration flowing, read on and discover the best pencil-skirt and shoe pairings. 

5 PENCIL-SKIRT AND SHOE PAIRINGS TO TRY

1. PENCIL SKIRT + KNEE-HIGH BOOTS

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(Image credit: @iliridakrasniqi )

Style Notes: Whilst we linger in this lukewarm winter, style your slim-fitting skirt with tights and knee-high boots—additional layers up top are optional. To get the proportions right, shop a pencil skirt that falls below the knee or lower, and style with either heeled or flat boots.

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2. PENCIL SKIRT + POINTED-TOE FLATS

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(Image credit: @abimarvel)

Style Notes: Copy the cool girls and swap your heels for flats this winter. Sharp, pointed-toe styles will work to elongate the body for a chic, '90s touch.

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3. PENCIL SKIRT + LACE-UP BOOTS

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(Image credit: @neelam.ahooja)

Style Notes: Juxtapose the feminine feel of the longer skirt by pairing it with some chunky, lace-up boots.

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4. PENCIL SKIRT + KITTEN HEELS

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(Image credit: @sylviemus_ )

Style Notes: One of my favourite combinations is a pencil skirt with kitten heels. This pairing works with any length of skirt, and you can add tights in the winter or go bare-legged when the sun comes out.

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5. PENCIL SKIRT + STRAPPY SANDALS

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(Image credit: @deborabrosa)

Style Notes: This tried-and-true pairing is the easiest way to enter party season with style. Dress this up with a backless top and re-wear it with a slim knit.

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Next Up: The Editor-Approved "Risky" Skirt Trend That Is Replacing Jeans This Winter

News Writer

Natalie Munro is Who What Wear UK’s news writer. Previously freelance commerce writer at British Vogue, Natalie’s experience spans journalistic and styling roles, which have seen her work on shoots for publications such as British Vogue, Vogue Ukraine, AnOther Magazine and Elle UK and write for publications including British Vogue and Conde Nast Traveller. With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news and trends for Who What Wear UK, with a particular focus on celebrity style and emerging fashion trends.