Kendall Agrees—Pencil Skirts Look Chicest With This Specific Shoe

Collage of Jennifer Lopez, Kendall Jenner and RHW wearing pencil skirts with pointed-toe heels.

(Image credit: Getty, Backgrid)

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published 7 October 2025

Sorry to the circle skirts that dominated over the summer months, but I've been studying the runways and scanning the celebrity scene, and it’s clear that the style set has reached a consensus: pencil skirts are taking over as the most significant shape of the season.

While they had an undeniable moment on the autumn/winter 2025 runways in February—not to mention the spring/summer 2026 runways that just wrapped—runway trends don't necessarily guarantee success amongst the street style set. Pencil skirts, however, officially have, and interestingly, every iteration comes with a very specific footwear formula.

Kendall Jenner wears a black low-rise pencil skirt with a black jacket and pointed-toe heels.

Catching my eye as she made her way into the Chanel front row to catch Matthieu Blazy's debut, Kendall Jenner wore a hip-slung pencil skirt that skimmed the knees, teamed with two-tone pumps featuring a razor-sharp pointed toe—a skirt and combination that elongated her frame while adding elegance in ways a ballet flat could never match.

A chic pairing for a number of reasons, this shoe and skirt formula elongates the leg by means of the pointed-toe detail. Meanwhile, the two garments riff off each other's inherent poise to reinforce a supremely chic silhouette.

Rosie Huntington-Whiteley wears a leather pencil skirt with pointed-toe heels and a black fur jacket.

Also spotted styling the elegant combination, model Rosie Huntington-Whiteley was out this week styling a leather iteration of the trending skirt silhouette with a luxuriously fluffy coat and a black pointed-toe heel.

Meanwhile, Jennifer Lopez styled a seafoam green ensemble with a black wide-brim hat and black pointed-toe heels, adding height to her frame and elegance to her outfit, while keeping her styling uncomplicated.

Jennifer Lopez wears a seafoam green pencil skirt with black pointed-toe heels.

A two-piece get-up that guarantees elegance, read on to discover my edit of the best pencil skirts and pointed-toe heels below.

Shop Pencil Skirts and Pointed-Toe Heels:

Marks & Spencer

Jersey Knee Length Pencil Skirt

The classic knee-grazing pencil skirt comes in UK sizes 6—24.

Mango

Kitten-Heel Patent Leather Shoes

The chocolate brown colour trend isn't showing any signs of slowing down, and these elegant heels are an easy way to tap into the enduring trend.

H&M

Pencil Skirt

Between the calf-length finish and the trending slate grey hue, there's something incredibly expensive-looking about this affordable skirt.

Zara

Heeled Shoes With Embossed Detail and Side Vents

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

COS

Cotton Pencil Skirt

The cotton composition ensures a lightweight finish that means this will style comfortably across the seasons.

H&M

Pointed Court Shoes

While pointed-toe heels are a natural paring for pencil skirts, they also look impossibly chic when paired with tailored trousers and jeans.

Reformation

Fig Preserve Skirt

Style this with a single-breasted jacket to pick up on the skirt and blazer trend that's set to dominate across the autumn months.

The Row

Liisa Pump in Leather

While I love these in the classic black, they also come in a dark beige and a fiery red.

Zara

Faux Leather Midi Skirt

I monitor trends for a living, trust me when I tell you that the leather pencil skirt trend is going to be huge this winter.

Massimo Dutti

Soft Nappa Leather Court Shoes

Style these with thick wool tights as we move towards the winter months, before going without once the weather starts to brighten.

Mango

Midi Pencil Skirt

When styled with a slightly sloughy knit, or even a boxy tee, a sleek pencil skirt feels nicely contrasted, creating a chic, unfussy silhouette.

& Other Stories

Classic Leather Slingback Pumps

In my opinion, ever great wardrobe begins with a classic pair of black heels.

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Natalie Munro is Who What Wear UK’s news writer and has worked in the fashion industry since she graduated with a degree in Journalism from the University of the Arts London. Natalie’s experience in the industry spans journalistic and styling roles that have seen her work for publications including British Vogue, Conde Nast Traveller, Vogue Ukraine, AnOther Magazine and Elle UK.

With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Reporting on a daily basis, Natalie focuses on trends on and off the runway, as well as street style and celebrity fashion. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.