Ava Gilchrist
It's official: pencil skirts are back. Naturally, our next step is to determine the shoes to wear with pencil skirts, especially if you haven't worn one in a few decades. (If you're yet to brave this silhouette's return, why not refresh yourself on how to wear a pencil skirt before perusing the footwear department?)
After retreating out of the limelight for the past few years, the sexy style is back hanging on the hips of those in the know. Unlike its '00s ancestors, 2025'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 elegance and style. Wondering how to look classy? This is it.
So, how are today's connoisseurs pairing pencil skirts with the right footwear to make the shape feel modern and not matronly? Ushered in by the resurgence of the '90s and Y2K fashion , the trend, which was formally the reserve of the office, has looped back and brought 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. (See: trainers.)
I've done the hard work for you and figured out how to make it work. Read on and discover the best pencil skirt outfits and their ideal correlating footwear options so you'l never ask what shoes to wear with pencil skirts again.
What Shoes Do You Wear With Pencil Skirts?
Consider this your guide to the ultimate 2025 shoe capsule wardrobe specifically curated for styles to wear with pencil skirts. As pencil skirts are quite fitted to the body, the best shoes to wear with pencil skirts are those that enhance the structure of the look. T
hese styles are usually polished like pointed-toe flat shoes, a sleek boot or an elevated kitten heel. Alternatively, soften the rigid fit with round-toe shoes like Mary Janes, ballet flats or penny loafers.
Historically, pencil skirts have been omitted from the canon of chunky shoes. It's rare we see a sporty trainer or buckled boot with the pencil skirt, but any longline shoe options can certainly balance out the formality of the garment.
6 Styles of Shoes to Wear With Pencil Skirts
1. Pencil Skirt + Knee-High Boots
Style Notes: While we linger in this lukewarm spring, 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 flat or heeled boots for the ultimate anti-trainer outfit.
Shop the Look:
This deep espresso shade is a major colour trend this year.
Style with a skirt that falls just below the knee or your favourite mini.
2. Pencil Skirt + Pointed-Toe Flats
Style Notes: Copy the cool girls and swap your heels for flats. Sharp, pointed-toe styles will work to elongate the body for a chic '90s touch, making it an ideal shoe to wear with pencil skirts as it plays into the tailored details of the piece.
Shop the Look:
This camel pencil skirt features a built-in belt hoop and knee-high slit.
Tory Burch's pierced ballet flats were a standout style at her Spring/Summer 2023 collection before becoming a mainstay at her New York Fashion Week last September. Fittingly, the eponymous designer styled hers both on the runway and in the front row with a pencil skirt, too.
3. Pencil Skirt + Mary Janes
Style Notes: For a more casual look, round-toe shoes like Mary Janes can help temper the rigidness of pencil skirts. I love how this pencil skirt is also made from suede and styled with a matching suede jacket, as the soft texture helps acheive a more lived-in effect.
Shop the Look:
Dress this down with a white T-shirt or up with a silk blouse.
The double strap feels like the footwear version of the dual or unnecessary belt trend that Bella Hadid helped pioneer.
4. Pencil Skirt + Kitten Heels
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.
Shop the Look:
Style with brown shoes for a chic, tonal look.
In my opinion, short kitten heels make for the perfect party shoes.
5. Pencil Skirt + Strappy Sandals
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.
Shop the Look:
If you love satin trousers, you'll adore this satin pencil skirt.
Black strappy heels are the wardrobe hero you didn't know you needed.
6. Pencil Skirt + Heeled Mules
Style Notes: If you've been hesitant to invest in this style because of their simplicity, consider the best shoes to wear with pencil skirts to be heeled mules, then. The raised sole brings a touch of primness and refinement to unfussy silhouettes, such is the case with this monochromatic look here.
Shop the Look:
This flared maxi skirt brings a bit more dimension and movement to your look.
Take it from Hailey Bieber, heeled mules are a staple.
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