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

It’s official: pencil skirts are back. After retreating out of the limelight for the past few years, the sexy style is back on the hips of those in the know. Unlike its ’00s ancestors, 2024’s pencil skirts look undeniably fresh. Void of bookish, stuffy or drab connotations, this season’s iterations utilise all of the learnings of yesteryear to create figure-hugging styles that top the charts for class, elegance and style. Ushered in by the resurgence of the ’90s and Y2K, the trend, which was formally the reserve of the office, has looped back, bringing with it fishnet tights and sharp kitten heels.

You might remember from the first time around that the skin-tight skirt isn’t the easiest to style. Trickier than a flowing maxi or a cute mini, a fitted pencil skirt looks amazing with certain shoe styles and less captivating with others. I’ve done the hard work for you and figured out how to make it work, so to get your inspiration flowing, read on and discover the best pencil-skirt and shoe pairings. 

Style Notes: Whilst we linger in this lukewarm winter, style your slim-fitting skirt with tights and knee-high boots—additional layers up top are optional. To get the proportions right, shop a pencil skirt that falls below the knee or lower, and style with either heeled or flat boots.

This deep espresso shade is a major trend this winter.

Style with a skirt that falls just below the knee 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 body for a chic, ’90s touch.

This grey pencil skirt looks more expensive than it is.

Style with socks and tights all winter long.

Style Notes: Juxtapose the feminine feel of the longer skirt by pairing it with some chunky, lace-up boots.

Dress this down with a white T-shirt or up with a silk blouse.

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

Style Notes: One of my favourite combinations is a pencil skirt with kitten heels. This pairing works with any length of skirt, and you can add tights in the winter or go bare-legged when the sun comes out.

Style with brown shoes for a chic, tonal look.

In my opinion, short kitten heels make for the perfect party shoes.

Style Notes: This tried-and-true pairing is the easiest way to enter party season with style. Dress this up with a backless top and re-wear it with a slim 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.

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