15 Pencil Skirts for An Easy, Put-Together Look

Never goes out of style.

Pencil Skirt Style Inspiration on Paloma Elsesser

@palomija/Design by Cristina Cianci

Nothing beats a classic, and a sleek pencil skirt is just that. While the name can conjure images of the '50s and Audrey Hepburn, this piece never went out of style and still has a talent for pulling together an outfit to this day. 

Pencil skirts, which today are versatile enough to complement a whole range of aesthetics, weren't as sleek as they are now when they first hit the scene. In 1908, Edith Berg tied a rope around the bottom of her skirt to hold it in place while riding Wilbur and Orville Wright's airplane. The look caught on and the hobble skirt, a traditional long style tied just below the knee, became a popular 1910s trend.

Over the years, the look continued to evolve. The '40s centered around intentional design, and in 1954, Christian Dior's H-line collection defined today's pencil skirt. Ever since, it's been an office and style staple without ever losing its recognizable shape.

Looking to work the iconic piece into your style, but not sure where to start? Scroll on to find 19 pencil skirt styles that would make a great addition to any closet.

Buttoned Pencil Skirt

For a meeting at the office, a classy evening out, or any time when you want a sleek and structured silhouette, you can't go wrong with a buttoned pencil skirt. Today, the high-waisted design is as much a trend as it is a staple, and a black one with gold buttons stands out while coordinating well with almost anything. Pair one with a crisp white shirt and flats for work, then switch into pumps for dinner that evening.

Anthropologie black button down skirt
Anthropologie Sunday in Brooklyn Cargo Midi Skirt $130.00
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Classic Black Pencil Skirt

If you're looking for a pencil skirt that's more versatile than any other, a classic black style is your answer. The one below features technology to accentuate curves, but still has the shape that made pencil skirts famous. Wear it with a bodysuit and blazer for the perfect anywhere, anytime look.

Theory black pencil skirt
Theory Classic Skirt in Sevona Stretch Wool $225.00
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Denim Pencil Skirt

Whether you want to feel especially put-together in denim or are looking for a pencil skirt that plays well with casual pieces, the denim pencil skirt is the best of both worlds. This black option is stretchy and textured and would look great with a classic white T-shirt and fashion-forward sneakers.

Front Slit Denim Midi Skirt
Cos Front Slit Denim Midi Skirt $130.00
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Fishtail Pencil Skirt

Pay tribute to Berg with a maxi-length fishtail pencil skirt that gathers at the knees before flaring out. Also easy to find in a knee length and a range of colors, this style would pair well with a tank top or bodysuit and may be the type of vintage-inspired piece you'd want to search for secondhand to find a truly unique version.

Khaite Fishtail pencil skirt
Khaite The Levine Skirt $480.00
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Tweed Pencil Skirt

Work gear doesn’t have to be boring, and you can make it less so with a tweed pencil skirt that features vibrant colors in a classic print. Pair this above-the-knee style with a coordinating blazer for full Clueless vibes, or try a bodysuit to make the tailored look work for a night out.

Tweed Pencil Skirt
Misook Tweed Pencil Skirt $220.00
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Lace Pencil Skirt

For a sophisticated, evening-ready feel, try a lace pencil skirt. Even though you can also wear it to work, the floral print and rich colors of this style make it elegant enough for celebratory events like engagement parties or baby showers.

Orange lace santorelli pencil skirt
Santorelli Ellie Lace Pencil Midi Skirt $295.00
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Leather Pencil Skirt

Nothing's sleeker than a leather pencil skirt, and the crocodile texture of this style takes it into full-on fashion territory. A front slit works great for a night out, so pair it with your favorite ankle boots and a statement crop top for a look to remember.

Good american black faux leather skirt
Good American Better Than Faux Leather Midi Pencil Skirt $139.00
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Knit Pencil Skirt

Many pencil skirts have a stiff feel, so if you want something a little more comfortable, try a knit style. This M.M. La Fleur Harlem Skirt ($198) is stretchy with side slits, making it great for everyday wear while still being posh enough for special occasions.

MM La Fleur Green Pencil Skirt
M.M. La Fleur Harlem Skirt La Fleur Harlem Skirt $195.00
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Ribbed Pencil Skirt

For another comfortable piece that still makes you look perfectly pulled together, try a stretchy ribbed style. Pair one with a coordinating tank to jump on the matching sets trend that's a current favorite for nights out.

Staud multi colored pencil skirt
Staud Karina Skirt $195.00
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Ruched Pencil Skirt

For a look that fits with the most modern interpretations on the pencil skirt, try a close-fitting, ruched style. Great for parties, casual drinks, a day out and about, or anything in between, this Norma Kamali number ($110) makes a statement alongside a minimalist tank and bold accessories.

Norma Kamali orange ruched skirt
Norma Kamali Shirred Skirt $110.00
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Belted Pencil Skirt

Nothing ties a pencil skirt together quite like a belt, and a pale pink shade is fun for warmer months. Pair this Club Monaco Piqué Belted Skirt ($180) with a neutral top and sneakers or polished sandals for a look that pops at your next brunch or wherever you decide to take it.

Club Monaco White pencil skirt
Club Monaco Pique Belted Skirt $180.00
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Satin Pencil Skirt

If you are looking to try the pencil skirt trend but want something a little fancier, the satin fabric is for you. Not only does it offer a more elevated take on the look, but it also feels more modern than some of the other options on this list. Some of our favorites include the Old Navy Satin Midi Slip ($40) and the Aritzia Babaton Slip Skirt ($55).

Old Navy black satin skirt
Old Navy Satin Midi Slip $40.00
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High-Waist Pencil Skirt

Pencil skirts hit at every level of the torso, but we are partial to the high-waist silhouettes. This area tends to be the smallest and cinching in helps create an hourglass silhouette.

Reona black suit skirt
Reona Bobbi Suit Skirt $175.00
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Checkered/Plaid Pencil Skirt

A printed pencil skirt can feel a little loud for some, but trust us, this piece is versatile. For example, the Altuzarra Belili Gingham Cotton Blend Skirt ($645) is on the pricier side, but we promise you will get your money's worth. Wear it with a black turtleneck for a more professional look or a cropped top for something a little more fun.

Altuzarra Black gingham Plaid
Altuzarra Belili Gingham Cotton-Blend Midi Skirt $995.00 $646.00
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Wrap Pencil Skirt

For a twist on the classic (literally), opt for a wrap pencil skirt. This adds some subtle ruching around the waist and the lower tummy. The Rails Adrienne Skirt ($198) comes in two ultra-chic colors and can be dressed up or down depending on your mood.

Rails satin tie skirt
Rails Adrienne Skirt $198.00
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