Sorry to the circle skirts that dominated over the summer months, but I've been studying the runways and scanning the Replica Handbags scene, and it’s clear that the most fashion-forward have reached a consensus: pencil skirts are taking over as the most significant shape of the season.
Whilst they had an undeniable moment at the autumn/winter 2025 shows 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, have got the official seal of approval, and interestingly, every excellent look I'm seeing uses a very specific footwear formula.
Catching my eye as she made her way to the Chanel front row for 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 whilst adding elegance in ways a ballet flat could never match. A chic pairing for a number of reasons, the pointed toe elongates the leg whilst both pieces riff off each other's inherent poise to reinforce a supremely chic silhouette.
Also spotted styling the elegant combination, model Rosie Huntington-Whiteley was out this week in a leather iteration of the trending skirt silhouette, paired with a luxuriously fluffy coat and black pointed-toe heels. Meanwhile, Jennifer Lopez wore a seafoam-green ensemble with a black wide-brim hat and matching pointed-toe heels, adding height to her frame and elegance to her outfit.
If you want a two-piece look that guarantees elegance, read on to discover my edit of the best pencil skirts and pointed-toe heels.
Shop Pencil Skirts and Pointed-Toe Heels:
The classic knee-grazing pencil skirt comes in UK sizes 6 24.
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.
Between the calf-length cut and the trending slate grey hue, there's something incredibly expensive-looking about this affordable skirt.
Honestly, I would easily believe you if you told me these were designer.
The cotton composition ensures a lightweight finish that means this will style comfortably across the seasons.
Pointed-toe heels are a natural pairing for pencil skirts, but they also look impossibly chic when paired with tailored trousers and jeans.
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.
I love these in the classic black, but they also come in a dark beige and a fiery red.
I monitor trends for a living, so trust me when I tell you that the leather pencil skirt is going to be huge this winter.
Style these with thick wool tights as we move towards the winter months, before going without once the weather starts to brighten.
When styled with a slightly slouchy knit or even a boxy tee, a sleek pencil skirt feels nicely contrasted, creating a chic, unfussy silhouette.
In my opinion, every great wardrobe contains a pair of classic black heels.
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Okay, Noted—the Most Elegant Dresser I Follow Just Traded In Her Dark-Wash Denim for This Controversial Color TrendIt looks so expensive.
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From Pilates in L.A. to Meetings in Paris, Kendall Jenner Can't Stop Wearing These Classic Designer FlatsI don't blame her—they look sleek and so comfortable.
