Pencil skirts have made a comeback, and they're being paired with this shoe trend by everyone.

      Apologies to the circle skirts that reigned during the summer, but after observing the runways and analyzing celebrity fashion, it's evident that leading style influencers have come to a unanimous decision: pencil skirts are emerging as the standout shape of the season. Although they enjoyed a notable presence during the autumn/winter 2025 shows back in February—and likewise at the recently concluded spring/summer 2026 runways—runway trends don't automatically translate to street-style popularity. However, pencil skirts have received official endorsement, and interestingly, every impressive outfit I’ve noticed incorporates a very specific footwear combination.

      (Image credit: Getty Images) I was captivated by Kendall Jenner as she arrived at the Chanel front row for Matthieu Blazy's debut, sporting a hip-slung pencil skirt that grazed her knees, paired with two-tone pumps featuring sharply pointed toes; this combination not only elongated her figure but also injected an elegance that ballet flats can't quite achieve. This stylish pairing is chic for several reasons—the pointed toe lengthens the leg, while both garments complement each other’s innate grace to create a remarkably stylish silhouette.

      (Image credit: Backgrid) Model Rosie Huntington-Whiteley was also seen in a similar elegant ensemble this week, wearing a leather version of the trending skirt shape, matched with a luxuriously fluffy coat and black pointed-toe heels. Meanwhile, Jennifer Lopez donned a seafoam-green outfit accentuated by a black wide-brim hat and coordinating pointed-toe heels, enhancing her height and adding sophistication to her look.

      (Image credit: Getty Images) If you're in search of a two-piece outfit that promises elegance, continue reading for my selection of the finest pencil skirts and pointed-toe heels. Shop Pencil Skirts and Pointed-Toe Heels:

      M&S Collection

      Jersey Knee Length Pencil Skirt

      This classic knee-length pencil skirt is available in UK sizes 6–24.

      Mango

      Kitten-Heel Patent Leather Shoes

      The trend for chocolate brown is still going strong, and these stylish heels are a simple way to embrace this ongoing color trend.

      With a calf-length design and a fashionable slate grey shade, this affordable skirt exudes a remarkably expensive appearance.

      Zara

      Heeled Shoes With Embossed Detail and Side Vents

      Honestly, I would easily believe you if someone told me these were designer.

      The cotton material provides a lightweight feel, making it suitable for styling throughout the seasons.

      Pointed-toe heels naturally complement pencil skirts, but they also look incredibly chic when paired with tailored trousers and jeans.

      Reformation

      Fig Preserve Skirt

      Pair this with a single-breasted jacket to tap into the skirt-and-blazer style trend that's poised to trend this autumn.

      The Row

      Liisa Pump in Leather

      I adore these in classic black, although they are also available in dark beige and a striking red.

      Zara

      Faux Leather Midi Skirt

      As someone who tracks trends professionally, I can assure you that the leather pencil skirt is set to be hugely popular this winter.

      Massimo Dutti

      Soft Nappa Leather Court Shoes

      These can be styled with thick wool tights as we transition into winter, and later worn without as the weather improves.

      When combined with a slightly loose knit or even a boxy tee, a sleek pencil skirt provides an appealing contrast for a chic and effortless silhouette.

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      Classic Leather Slingback Pumps

      In my view, every excellent wardrobe should include a pair of classic black heels.