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14 Pencil Skirt Outfits to Update a Classic Staple

This workwear basic can be so much more.

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After Christian Dior introduced the modern pencil skirt in the 1950s, the narrow, knee-length skirt has been a mainstay of offices everywhere. Whether you're wearing it as part of a skirt suit or as a separate, it's a ubiquitous part of work culture. But! If you've only ever thought about a pencil skirt in the context of your job, it can be an item of clothing that can be surprisingly versatile—even playful, when paired with the right top. Giving this old favorite a Clueless-like makeover is also possible by choosing pencil skirts in different cuts and colors for a cooler professional look. Like the blazer and the heeled shoe, it's absolutely possible to operate within a framework and still make some fantastic work outfits. So much the better if you work in an office where the dress code isn't as strict—it allows you to play around with length and even be a little daring.

If this sounds appealing (or even if you just want some inspirational photos to see what we're talking about), keep scrolling for some work- and play-appropriate pencil skirt outfits you can emulate now.

Simple Black

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If you're a working professional, chances are you've owned a pencil skirt. But that doesn't mean it has to be boring—the length doesn't have to stop at the knee, as we see here, and can be a more lengthening midi. It can still look professional with a matching vest (just put a collared shirt on underneath if your office dress code leans conservative).

Plain White

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A white pencil skirt is, similarly, a ubiquitous work staple—and often takes the place of a black pencil skirt in the warmer months. A simple, stark white skirt lends itself nicely to tonal dressing (going head-to-toe white) and adding a cool belt and shoes for some polish.

For a Tonal Look

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If you have a pencil skirt in a neutral color like navy, it pairs beautifully with a similarly colored jacket and shirt. You could go full tonal if you have blue shoes, but why not give the outfit some visual interest? Not everyone has gold shiny boots, sure, but a multitude of colors would work here.

As a Color Moment

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If you're anything like me, your workwear staples are pretty basic—meaning, I don't have a bright pink pencil skirt to break out when I'm feeling fun. But if you're dying to dress up your professional attire, a pencil skirt is the perfect way to take a silhouette you're already familiar with and change one thing (getting one in a cool color) to make it more interesting.

With a Peplum

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Technically this might be two skirts on top of each other (which is also a cool look!). But if you'd rather not play with the color of your skirt, try the shape instead. The top layer of the skirt flares out, and then the bottom continues down your legs. It's simultaneously lengthening and figure-accentuating.

In a Lighter Hue

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I would actually argue that the fall and winter months are exactly the right time to break out a fun, light color—it'll instantly lighten your mood even if the weather is gray outside. Butter yellow is "trendy" but it's also a lovely classic color, especially when paired with a similar hue on top. Swap the pink shoes for black or nude for a more subdued approach.

In Body-Con Style

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Pencil skirts can also come in tighter, more form-fitting styles. Obviously, this isn't for everyone, but they can still be appropriate for an office environment. For a figure-flattering style, search for a body-con skirt in a heftier material that nips in at the waist and then hugs close to your form without being tight. As we see here, a midi feels more work-ready than a mini.

In a Pattern

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Splashes of color and print are an easy way to add visual interest to any wardrobe. If you don't want to let go of black completely, how about experimenting with bold patterns that add to the classic color in an unexpected yet complementary way?

With Buttons

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I won't lie, I've been daydreaming about this cozy set—imagine how comfortable you'd be at work! The joys of a button-up skirt are manifold, but primarily, you can wear it in a number of ways, and you can choose how much of your legs you want to show depending on how many buttons are buttoned.

Showing Some Skin

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Showing a hint of skin really depends on the type of office you work in—it's probably not going to fly at a bank, for example, but it would potentially work for a cool, edgy startup! This particular pencil skirt is probably more appropriate for a work cocktail event, but surprising cutouts and slits can make for a fun silhouette (and you can always wear tights underneath if you don't want to show skin).

As a Matching Set

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The skirt suit does not have to be boring! This green snake skin-printed skirt with a matching jacket feels very appropriate for a work meeting (including the tights under the skirt), but it's still got a ton of eye-catching intrigue in the color, contrasting collar, and oversized shape.

In Denim

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This would fall under business casual if you were wearing this at work—and would make an awesome alternative to jeans if you were going out to dinner or drinks. The tulle lace insert seen here keeps the skirt from feeling too casual with its romantic frilly flare.

With a Mid-Mini

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This is not a mini-mini skirt (as in, you can still sit down and move around in it), but it does hit above the knee. Pairing this style with black tights can help you feel a bit more elegant, and add a long blazer in a different color so that it just nearly grazes the bottom of the skirt hem for a more put-together look. This clever styling reads thoughtful yet effortless.

With a Pretty Two-Piece

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If you're really hoping to spice things up, combine color and pattern for a pencil skirt that's bursting with personality. Here, it's paired with a matching top—which is very similar to a dress except for the delineation at the waist—and a trench with a slightly longer length helps bring dimension to the look.

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