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.
5 PENCIL-SKIRT AND SHOE PAIRINGS TO TRY
1. PENCIL SKIRT + KNEE-HIGH BOOTS
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.
Shop the Look:
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 this winter. Sharp, pointed-toe styles will work to elongate the body for a chic, '90s touch.
Shop the Look:
3. PENCIL SKIRT + LACE-UP BOOTS
Style Notes: Juxtapose the feminine feel of the longer skirt by pairing it with some chunky, lace-up boots.
Shop the Look:
Dress this down with a white T-shirt or up with a silk blouse.
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:
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:
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
Natalie Munro is Who What Wear UK’s news writer. Having worked in the fashion industry since her time at university—where she obtained a BA in Journalism from University of the Arts London, Natalie's experience spans journalistic and styling roles. In the early stages of her career Natalie predominately worked on editorial shoots for fashion publications such as British Vogue, Vogue Ukraine, AnOther Magazine and Elle UK, before moving into journalism roles.
On completion of her degree she interned in the editorial team at British Vogue and later went on to freelance for the publication. Here, she developed her interest in reporting on the latest fashion news and trends. Inspired by the dynamic nature of the industry, Natalie went on to write for other lifestyle and fashion brands and publications before taking on the role as News Writer for Who What Wear.
With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Focusing on trends on and off the runway, as well as street style and celebrity fashion, Natalie reports on a daily basis, ensuring that she remains ahead of the trends. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.
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