Pencil skirts are making a comeback, and everyone is pairing them with this style of footwear.

      Apologies to the circle skirts that ruled the summer months, but after observing the runways and celebrity fashion, it’s evident that the style-savvy have reached a consensus: pencil skirts are becoming the key silhouette of the season. While they made a notable appearance at the autumn/winter 2025 shows in February—along with the recently concluded spring/summer 2026 runways—runway trends do not always ensure success in street style. However, pencil skirts have received the official stamp of approval, and interestingly, every standout look I’ve come across features a specific footwear pairing.

      (Image credit: Getty Images) Kendall Jenner caught my attention as she arrived at the Chanel front row for Matthieu Blazy's debut, wearing a hip-slung pencil skirt that grazed her knees, paired with two-tone pumps that had a sharp pointed toe. This combination not only elongated her silhouette but also added an elegance that ballet flats cannot replicate. This stylish pairing is chic for several reasons: the pointed toe stretches the leg and both pieces complement each other’s sophistication, creating a truly refined look.

      (Image credit: Backgrid) Also seen sporting this elegant ensemble, model Rosie Huntington-Whiteley was out this week in a leather version of the on-trend skirt style, matched with a luxuriously plush coat and black pointed-toe heels. Meanwhile, Jennifer Lopez opted for a seafoam-green outfit complemented by a black wide-brim hat and matching pointed-toe heels, enhancing her height and the elegance of her ensemble.

      (Image credit: Getty Images) If you're looking for a two-piece outfit that guarantees sophistication, keep 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 timeless knee-length pencil skirt is available in UK sizes 6–24.

      Mango

      Kitten-Heel Patent Leather Shoes

      The chocolate-brown color trend shows no signs of fading, and these stylish heels offer an effortless way to embrace this ongoing trend.

      The calf-length cut combined with the trending slate grey color gives this affordable skirt a look of luxury.

      Zara

      Heeled Shoes With Embossed Detail and Side Vents

      I would easily believe you if you said these were designer items.

      The cotton material provides a lightweight finish, making it comfortable to wear throughout the seasons.

      While pointed-toe heels naturally pair well with pencil skirts, they also look incredibly chic with tailored trousers and jeans.

      Reformation

      Fig Preserve Skirt

      Pair this with a single-breasted jacket to embrace the skirt-and-blazer trend that’s set to be significant this autumn.

      The Row

      Liisa Pump in Leather

      I adore these in classic black, but they also come in dark beige and vibrant red.

      Zara

      Faux Leather Midi Skirt

      Given my profession of tracking trends, trust me when I say the leather pencil skirt is going to be major this winter.

      Massimo Dutti

      Soft Nappa Leather Court Shoes

      Style these with thick wool tights as we approach winter, then wear them bare when the weather brightens up.

      When paired with a slightly oversized knit or a boxy tee, a sleek pencil skirt creates a lovely contrast, resulting in a chic, effortless silhouette.

      & Other Stories

      Classic Leather Slingback Pumps

      I believe that every great wardrobe includes a classic pair of black heels.