More than 70 years later, designers are sharpening it once again. Pencil skirts led the charge across the autumn/winter 2025 runways, appearing at Gucci in Milan and Miu Miu in Paris. Rather than simply reviving boardroom dressing, both houses made the shape feel considerably less corporate: Gucci styled slit versions with sheer lingerie and sumptuous outerwear, while Miu Miu leaned into deliberately feminine layers, colourful tights and plenty of personality.
The good news is that today’s pencil skirt no longer requires a matching blazer, court shoes or an Outlook calendar packed with meetings. Because the silhouette fits closely through the leg, I personally prefer mine with a kitten heel or pointed toe, which helps to visually lengthen the line.
The gorpcore girls and athleisure crowd would almost certainly disagree, however, and make a convincing case for wearing one with Salomon trainers, sporty layers and an enormous nylon jacket. Consider the pencil skirt’s new job description pleasingly flexible.
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Ahead, a fashion writer’s guide to styling the pencil skirt in 2026.
A leather pencil skirt with western boots
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A leather pencil skirt can veer a little CEO if you’re not careful, which is where a pair of western boots comes in. The boots take the polish down a notch and make the whole thing feel better suited to Saturday lunch than a boardroom. Add a simple T-shirt, slouchy knit or a cropped denim waistcoat, and keep the rest of the outfit unfussy. Extra points for a skirt with a front split, mainly because those western boots are made for walkin’.