49 Pencil Skirt Outfits that Will Make You Look Like a True #Girlboss


A pencil skirt is an incredibly versatile clothing item. You can use it to create a no-fuss office look that will impress your boss, pair it with a crop top for a crazy night out, or wear it as part of a suit to turn heads at the next office meeting. It goes with a wide variety of shoes, so it’s wearable practically every season. Most importantly, it highlights your silhouette in a subtle way, so you can look feminine and professional at the same time.

Pencil Skirt Outfits

Pencil Skirt Outfits



Every woman should invest in a few quality pencil skirts, especially if they have a job that entails wearing business attire for most of the time. We’ve gathered a few looks from around the Internet to show you how a pencil skirt can be the base for an outfit that will make you look like a true #Girlboss.

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Pair your pencil skirt with a denim shirt and nude heels to get the best #neutrallife look possible. A clutch goes perfectly with this dazzling ensemble.

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For a bit of color, opt for a red shirt and accessorize your outfit with a statement necklace. You will look professional and chic in no time.

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A pencil skirt doesn’t have to be boring. A colorful print will elevate your mood and give your outfit a bit of a pop. Pair it with a simple shirt, to keep things classy.

Fall Outfit: Pencil Midi Skirt

A fancy belt and a sheer shirt will help you create a feminine look, perfect for a first date. Heels are mandatory.

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If you would prefer to keep things simple, this is the outfit for you. Recommended for those days when you need to look flawless with minimal effort.

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Accessories can really make a pencil skirt outfit stand out from the crowd. Case and point: that interesting scarf is the perfect addition to an otherwise plain (and even a bit boring) outfit.

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If you’re looking for something more edgy, a denim pencil skirt can certainly turn heads, especially when paired with a plain white tank.

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This beautiful lace pencil skirt is dressed down with a denim shirt for a spectacular result. Since we’re on the subject, nude pumps are also a mandatory purchase for every fashion enthusiast out there. They go with almost everything.

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An oversized belt highlights your waist and helps the outfit pop.

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Another great example of a patterned pencil skirt, this time paired with a denim shirt. As you can see, keeping things simple in the upper half allows the skirt to make a more powerful impression.

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Do you have a date or cocktail party after work? No problem! This top might not be office-appropriate, but it goes well with the skirt and will look great with a blazer. Once you leave the office, take the blazer off and update your look in seconds without having to go home and change.

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We love the color on this gorgeous ensemble, proving that pencil skirts don’t always have to be plain and business like.

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For an eye-catching party look, pair a pencil skirt with a crop top.

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Your boss might disapprove, but the crowd at the bar will surely applaud your look. Wear a shirt over the top during the day to avoid condemning glances from coworkers or supervisors.

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Dress up your pencil skirt with a funky top to give the look a bit of an edge.

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Pencil skirts look great as part of a power suit. Opt for a lace top underneath the blazer to soften the look and showcase your femininity.

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You can wear pencil skirts every season. During fall, they look awesome with tights, boots, and a colorful sweater.

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Wear your power suit with a plain shirt to look uber-professional. The pearls will help you stand out from the crowd.

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The print on this skirt is gorgeous. Plus, the red bag adds a much-needed pop of color to this black and white ensemble.

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Miranda Kerr can rock any outfit, and the pencil skirt is no exception. Here, she decided to pair her patterned skirt with a simple, yet effective top and black heels. No wonder she’s a style icon.

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Black pencil skirt + white shirt = office perfection.

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The same combination, this time with an oversized belt which draws attention to the waist.

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We are big fans of floral prints, so we simply adore this look. As we’ve said before, nude pumps really seem to go with everything. Don’t you agree?

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A faux leather black pencil skirt works well on any silhouette, even if you don’t have Blake Lively’s curves. Pair the skirt with high heels and your legs will look longer.

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Wear this outfit to a business lunch or cocktail party. It’s the perfect amount of daring for the office.

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Blazers are all the rage when it comes to what to pair with a pencil skirts, but cardigans can work well also.

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Horizontal stripes can create the illusion of curves, so avoid this type of pattern if you’re already curvy. Pair it with a white top to keep things simple. By the way, we’re obsessed with these oversized earrings.

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A power suit worthy of a #Girlboss. For when you really want to impress your manager.

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You can wear patterned pencil skirts at the office as long as you pair them with something simple in the upper half.

NEW YORK, NY - JANUARY 31: Miranda Kerr is seen in Downtown Manhattan on January 31, 2014 in New York City. (Photo by Alessio Botticelli/GC Images)

Miranda Kerr strikes again with the perfect all-black ensemble for when you want to go back to basics.

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A lace pencil skirt that screams summer. It will certainly turn heads.

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The devil is in the details, as they say. As far as style is concerned, some funky details can certainly spice up a plain black pencil skirt.

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Add a zipper into the mix to make the entire outfit sexier. Pair the skirt with a top that showcases your cleavage and you have the perfect look for date night.

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Fan of buttons? Make them work for your advantage. And add a long necklace to give the entire outfit a hint of glam.

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If you want to kill it at a networking event, go for an elegant all-black ensemble.

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A cozy look for those rainy fall days. Trench coats go great with pencil skirts.

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A pop of color can do wonders for an otherwise plain outfit.

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She’s bringing sexy back.

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Classy and chic.

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Pencil skirt, fluffy sweater, oversized sunglasses, and messy bun make for a stylish look.

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Rock some polka dots for a more playful but still utterly professional look.

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Animal prints look great on pencil skirts, as long as you keep the top simple.

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Showcase your figure with this interesting pencil skirt and a plain crop top.

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An autumn pattern for the perfect business look.

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The glittery clutch adds a drop of glam to this office ensemble.

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Don’t be afraid of colors. Life can be boring in black and white.

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Taylor Swift is the queen of crop tops, and she loves to pair them with pencil skirts. Don’t be afraid to follow her lead.

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A powerful flower print that will surely help you stand out from the crowd.

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This shade of purple is mesmerizing.

As you can see, the pencil skirt may have started as an office essential, but that doesn’t mean that this versatile piece of clothing is strictly business. With the right accessories and styling, you don’t have to worry about ending up with a plain librarian look. More importantly, a pencil skirt can be worn with a variety of blouses and blazers, which means that you will get plenty bang for your buck. Here are a few additional tips to keep in mind when creating an outfit that revolves around a pencil skirt:

  • A pencil skirt is extremely flexible. It’s easy to dress it up for parties or dress it down for a casual look. You can wear it with a dress shirt at the office and pair it with a tee in the evenings. Or you can keep things simple and opt for a basic tank top for a casual day look.
  • Tucking in your top or shirt adds a more sophisticated touch to your look, elongates your legs, and created a trimmer looking waist. It’s especially recommended to tuck in the top when wearing a high waist skirt, for a more dazzling effect. If you’re petite, wear a top in a similar color as a skirt, to avoid shortening your torso.
  • Don’t want to tuck in the top? If you’re going for a loose top, you should then wear a belt to look more pulled together.
  • Pencil skirts can look good on all body shapes. If your problem area is your bottom half opt for a skirt in a solid color and pair it with a textured sweater or patterned blouse. If you want to look slimmer, pair it with a deep V-neck shirt or top. When you want to achieve an hourglass silhouette, make use of belts or try a peplum top. Finally, if you’re slim and want to create the illusion of curves, go for a skirt with a pattern or bold print.
  • If you’re plus size, don’t shy away from the pencil skirt. Instead, go for a high-waisted one with a shorter hemline – the style really suits your body type and it can make you look slimmer.
  • Make sure you buy the right fit. Your pencil skirt should always look smooth – if the skirt has bumps or rolls when you stand up straight, it’s way too tight. Go up a size. A skirt that’s too tight won’t look very flattering; plus, it will make everyday activities like walking or sitting at your desk more unpleasant. No one wants that.
  • Pencil skirts look gorgeous with heels, but they can be paired with flats as well, for a more casual look. Opt for flats that match the color of the shirt. You can add some funky bright jewels to spice up the look.
  • When it comes to perfect outerwear pieces to combine with pencil skirt, you will never go wrong with a leather jacket of denim jacket in spring/summer, and a trench coat in autumn/winter.
  • A pencil skirt works for after-work events as well. You can add instant glam to your pencil skirt with some sparkling jewelry or a colorful statement necklace. Heels work best in this instance, but you can also keep some ballet flats in your back to resort to once the event is over.
  • While wearing a pencil skirt with a crop top is a great way to show some skin and create an eye-catching look, it might not be the best idea for the office. The good news? You can tone down the outfit with a blazer or cardigan.
  • Kim Kardashian is the queen of rocking pencil skirts with sheer tops and blazers, so you can follow her style if you want to create an elegant evening look. Pencil skirts are great for cocktail parties, and a sheer shirt will make you look feminine and professional at the same time.
  • Another fun way to express yourself with the help of pencil skirts? Color blocking. Just make sure that the darker side covers the areas of your body you’re trying to conceal and the lighter shade showcases your best features.
  • For winter, pair your pencil skirt with thigh high leather boots. They will keep your legs warm while adding just the right amount of texture to your look. Alternatively, it also goes well with an oversized sweater and ankle boots.
  • What about length? If you’re petite, you should opt for a skirt that sits right about the knee, as this style will create the illusion of longer legs. If you’re of average height or tall, then the hemline of the skirt should hit you at the smallest point of your legs – usually above or below the knee. At the end of the day though this is strictly a matter of personal choice, so feel free to experiment with different lengths to see what fits you best.

All in all, the pencil skirt is a mandatory part of any style arsenal. It’s classy, flexible, and timeless. If your wardrobe doesn’t include one, it’s clearly time to do some shopping. We’re talking about an investment piece, so it will be worth every penny.


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