The Best Dressed Women Agree, *This* Is the Chicest Shoe Trend to Wear With Pencil Skirts

The feeling of spring is finally in the air, and for those of us, especially in New York, the excitement is palpable. We're getting through the days by looking forward to shedding winter layers and swapping our favorite jeans or trousers for skirts. The pencil skirt, a fitted, knee-length silhouette that tapers from the waist to the hem, is the trend currently dominating our thoughts. Its clean, sophisticated aesthetic and runway endorsement—seen in the spring 2026 collections of brands like Khaite, Saint Laurent, and Tory Burch—have made it a favorite among the fashion insiders. While versatile with a range of footwear, the current go-to pairing for the best-dressed women is knee-high boots.

It girls like Bella Hadid and Hailey Bieber are championing the pencil skirt and knee-high boot combination. During Paris Fashion Week, Hadid was spotted in a vintage Fendi skirt and a white long-sleeve shirt, elevated with tan heeled knee-high boots and a suede Prada tote. Meanwhile, on her trip to Tokyo, Bieber wore a leather pencil skirt styled with a leather blazer, a V-neck sweater, and black sock-like knee-high boots.

In the past, the styling rule dictated that the skirt hem had to overlap the top of the boot to create a polished, streamlined look. However, in 2026, Hadid and Bieber are challenging this idea. They demonstrate that showing your kneecaps is now the chic way to go. Plus, it provides a welcome bit of breathability on warmer spring days.

If Hadid and Bieber have inspired you to embrace the pencil skirt trend and pair it with knee-high boots, keep scrolling because I've curated an edit of the best styles for both.

On Bella Hadid: Fendi skirt; Dôen Lidie Tee ($178); Saint Laurent Francoise Leather Knee-High Boots ($2150); Prada Bonnie Bag ($3650)

Shop Pencil Skirts and Knee-High Boots:

Susana Monaco

Faux Leather Pencil Skirt

Replicate Bieber's look by pairing this skirt with brown knee-high boots and a V-neck sweater.

Open Edit

Elara Pointed Toe Knee High Boots

You can't go wrong with this classic pair.

Size down for the best fit.

Saint Laurent

Francoise Smooth Leather Knee-High Boots

The exact pair that Hadid wore.

Understated Leather

Handkerchief Leather Skirt

There's no need to go through racks of clothing when this vintage-like skirt exists on Revolve.

Sam Edelman

Sylvia Knee High Boots

If you're in the market for an under-$300 black boot, this pair is for you.

Style with a white tank and neutral knee-high boots.

Reformation

Remy Stretch Knee Boot

These boots fit like a glove but aren't too tight on the legs.