How to Wear a Pencil Skirt


Hi Imogen, Please tell me how to master the pencil skirt, including – which shoes can you wear with a pencil skirt other than the classic (and extremely painful!) pump.

How to wear a pencil skirt

Here are just a few ideas of how to style a patterned pencil skirt.

The trick with shoes, particularly if you’re not a fan of the pump, is to make sure the shoe isn’t chunky.

Styling the Pencil Skirt
What’s your favourite way to wear a pencil skirt?


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  • I love to wear mine with heels – but I have to mention that I do not usually wear any heels over 3 cm, and all of my open shoes have a mary jane-style strap for extra comfort.
    When I want to go for a more casual look, I combine my pencil skirts with a fitted t-shirt or casual sweater and canvas shoes, not Converse, but something a bit more slim and feminine. Here in Spain that would be Victorias, they come in many colours and have a juvenile retro-vibe, but I’m certain you can find that style of shoe everywhere.

    • I don’t know what the experts say, but I have an X-shape and I love to wear pencil skirts with a fitted top. I have taken mine to the tailors to have the waists taken in, because they were a bit loose, but know they just show off my waist beautifully.

  • I have a couple of pencil skirts, and the shoe depends on the length. My shorter skirt looks better with a ballet flat, and my longer skirt with heels. I have a 40s styled heeled sandal that I love, and it looks beautiful with my longer pencil skirt and a nice blouse (t-strap style sandal). The shorter pencil skirt really doesn’t look good with anything except flats – anything with a heel would make it look too aggressive.

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