Not All Shoes Go With Pencil Skirts, But These 5 Definitely Do

It’s official, pencil skirts are back. After ebbing out of the limelight for the past few years, the sexy style is finally back on the hips of those in-the-know. Unlike its ’00s counterparts, 2024’s pencil skirts look undeniably fresh. Void of bookish, stuffy or drab connotations, this season’s styles have utilised all of the learnings of yesteryear, to create figure hugging styles the top the chats for class, elegance and style.

Ushered in my the ’90s and ’00s resurgence, the office siren trend has looped back, and with it, fishnet tights, sharp kitten heels, and figure-hugging pencils skirts have all arrived in tandem. Whilst you might have been a fan during its initial popularity, the skin-tight skirt isn’t always the easiest to style. Trickier than a flowing maxi or a glamorous mini, a fitted pencil skirt looks amazing with certain shoe styles, and less captivating with others. To get your inspiration flowing, read on to discover the best pencil skirts and shoes pairings of the season.

Style Notes: Whilst we linger in this chilly winter, style your slim-fitting skirt with thick tights and knee high boots. To get the proportions right, shop a pencil skirt that falls below the knees or lower, and style with heeled boots or flat styles.

This deep espresso shade is a major trend this winter.

Style with a knee-length skirt or your favourite mini.

Style Notes: Copy the cool-girls and swap your heels for flats this winter. Sharp, pointed toe styles will work to elongate the look for an effortless look with a chic ’90s touch.

This grey pencil skirts looks more expensive than it is.

Style with socks and tights all winter long.

Style Notes: Juxtapose the feminine feel of the structured skirt, and pair with some chunky lace-up boots.

Dress this down with white t-shirt and up with a silk blouse.

Lace-up boots are due a huge revival next season.

Style Notes: One of my favourite combinations out there, the pencil skirt and kitten heel pairing works with any length of skirt. Style with tights in the winter, and go bare-legged when the sun comes out.

Style with brown shoes for a chic tonal look.

In my opinion, short kitten heels are the perfect party shoe.

Style Notes: This tried-and-true pairing is the easiest way to enter party season with style. Dress this up with a backless top, or down with a fine-knit.

This maxi pencil skirt is at the top of my wish list.

Gold heels are the wardrobe hero you didn’t know you needed.

Up Next: The Editor-Approved “Risky” Skirt Trend That Is Replacing Jeans This Winter

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