50 of the Best Pencil Skirts

by Kathleen Loxton
3 colourful pencil skirts

Pencil skirts, created in 1954 by Christian Dior, are today found in every fashionistas closet thanks to their versatile nature and seasonless appeal. From how to wear a pencil skirt to finding that top to wear with pencil skirt inspiration, we’ve put together 50 stunning pencil skirt looks. This collection of pencil skirt outfit ideas and expert guide to what to wear with a pencil skirt will help style the perfect skirt outfit for you!

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How to Wear Pencil Skirts During the Day

Pencil skirt outfits for the daytime are all about sorting through what tops to wear with skirts. Tops to go with skirts can include slogan t-shirts, simple shirts, blouses or sweaters. In terms of skirt and top outfits a shirt or blouse and pencil skirt combo are an effortlessly stylish and quick look to throw together.

For cooler seasons or a changeable climate, a pencil skirt with boots and layered jacket or coat is an ideal solution to what to wear with a pencil skirt. When the temperature rises heels, pumps and flats are the perfect match for a light top and pencil skirt; they also look great with sunglasses and hats! What top to wear with a tube skirt can follow much the same pattern, simply see the examples of tube skirts how to wear below.

A black pencil skirt outfit doesn’t have to be boring and you don’t need to steer clear of colour. A red skirt outfit can make for a striking fashion moment, but when choosing what to wear with a red skirt go for a monochrome top, or muted layers so that the main piece takes the focus. Colour blocking or print mixing is always another option for when you’re feeling bold.

Woman in yellow pencil skirt and white shirt - 50 best pencil skirts
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Woman in pink pencil skirt and white top - 50 best pencil skirts
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Woman in red aztec print pencil skirt - 50 best pencil skirts
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Woman in red pencil skirt with fringe detail and slogan t-shirt - 50 best pencil skirts
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Woman in back and white check pencil skirt - 50 best pencil skirts
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Christine Teigen in black and white print pencil skirt - 50 best pencil skirts
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Girl in dark grey pencil skirt and t-shirt - 50 best pencil skirts
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Hilary Duff in grey pencil skirt and white top -- 50 best pencil skirts
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Olivia Palermo in black pencil skirt with slit and a jumper - 50 best pencil skirts
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Woman in yellow pencil skirt and coat, fashion week street style - 50 best pencil skirt
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Woman in light beige pencil skirt and blazer - 50 best pencil skirts
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Woman in red pencil skirt with front slit and a pink shirt - 50 best pencil skirts
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Emma Watson in black pencil tube skirt, trench coat and white top - 50 best pencil skirt
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Rihanna in red pencil skirt and coat - 50 best pencil skirts
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Woman in purple lace overlay, leather jacket and slogan t-shirt - 50 best pencil skirts
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Celebrity pencil skirt looks for the day

Now here are some celebrities who know how to rock a pencil skirt! A perfect example of what top to wear with a pencil skirt these women show how pencil skirts can go from classic and feminine, to chic and sophisticated.

How to wear pencil skirts during the day - Emilia Clarke in blue and white pencil skirt and striped skirt

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 How-to-wear-pencil-skirts-during-the-day-Meghan-Markle-in-blue-pencil-skirt-and-coat-with-red-handbag

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How to Wear Pencil Skirts at Night

With a simple few tweaks, selecting what to wear with pencil skirt ensembles can turn pencil skirt outfits into a lovely nighttime look. Black pencil skirt outfits may be your first port of call, so a leather pencil skirt outfit or black lace skirt outfit can make your garments dressier for an evening out. Then for the final touch, nailing the tricky element of tops that go with pencil skirts.

Pencil skirts and tops for a nighttime look can include a little bit of sparkle or luxurious fabric mixes to elevate your style. For an elegant approach remember to balance heel and hem height and focus on more structured or delicate tops to finish the look. Finally, the colour palette of your pencil skirt can play in to a chic all-black look, a feminine soft pastel outfit, or a stylish put-together outfit.

Alexa Chung wearing silver sequined pencil skirt and sweater
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Victoria Beckham in leopard print pencil skirt
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Model in black lace pencil skirt and v-neck black top
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Sandra Bullock back shirt and black pencil skirt
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Olivia Culpo in red and pink pencil skirt and a red sweater
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Blake Livley in black pencil skirt, heels and black top
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Model in coral pencil skirt and black top
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Fashion week street style woman in black pencil skirt with graphic design and a black blouse
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Fashion show model in sequined pencil skirt
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Kate Hudson in black leather pencil skirt and hot pink blouse
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Miranda Kerr in pink and black pencil skirt and black shirt
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Model wearing white lace pencil skirt and pink blouse
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Rosie Huntington Whitley wearing a red print pencil skirt and a pink shirt
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Emily Ratajkowsk wearing black pencil skirt and crop top
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Model in lace black pencil skirt and jumper
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Celebrity pencil skirt looks for nighttime

Follow Lily Aldridge’s example when it comes to searching through your closet to find that top to wear with pencil skirt and heels for a night on the town. A classy and sexy style is achieved by the demure length pencil skirt, while the off-the-shoulder blouse cut, and leather element meant that it’s anything but boring! Pencil skirts styled in this way aren’t fussy, old-fashioned or too casual either. It’s all about the accessories that partner them!

Lily Aldridge in black leather pencil skirt and blue blouse with floral print

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How to Wear Pencil Skirts for Work Whatever Your Industry

A good capsule professional wardrobe will always include a black and white skirt outfit and suitable tops for pencil skirts. Whether you’re running the board room or out on assignment, classic combos like a black and white skirt outfit never go amiss. However, getting stuck in a rut for black pencil skirt outfit ideas is a common hazard. Being thoughtful over what accessories and tops to wear with pencil skirts can turn a blasé relationship with your black pencil skirt outfits into a new closet asset and style skill.

There’s plenty of ways to recreate this classic ensemble however, a white pencil skirt outfit or more colourful option can still be a professional and fresh take. Polished blouses, shirts and sweaters are a great partner for pencil skirts; not to mention always work appropriate and versatile for desk-to-dinner occasions. Office wear, like the way we work, is changing. Branch out with your pairing choices and you’ll never have to dread what to wear with a black pencil skirt again!

Jemma Dewan in white pencil skirt and black blouse
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Kate Bosworth in brown pencil skirt and white shirt
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Olivia Palemero in burgundy pencil skirt and jumper
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Lily James in white pencil skirt and checked shirt
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Queen Letizia in red pencil skirt and white top
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Jessica Alba in black pencil skirt and white shirt with tie detail
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Model in floral pencil skirt and gingham shirt
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Model in black pencil skirt and green top
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Model in grey skirt and black blouse
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Model in pink top and polka dot pencil skirt
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Woman in cream pencil skirt and white blazer
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Model in red sweater and checked pencil skirt
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Carine Roitfeld in green and blue pencil skirt and black shirt
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Kate Bosworth in blue-green pencil skirt and black roll neck top
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Kate Bosworth in brown pencil skirt and yellow and black top
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Celebrity pencil skirt looks for work

Still debating what to wear with a black pencil skirt or white pencil skirt outfit? Olivia and Reese show us that skirt and top outfits can be extremely successful with concerted effort and smart choices – just like any brilliant business deal! Always try tops tucked-in and untucked to see what looks best, and remember belts are the best additions in this area!

Reese Witherspoon in blue pencil skirt, pink heels and blue blouse

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Olivia Palmero in light blue pencil skirt and navy shirt

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Final Note: 50 of the best Pencil Skirts

● Pencil skirts have been a wardrobe essential since they were first designed by Christian Dior in 1954.
● Pencil skirt and top combinations for the day include; casual shirts, jumpers, and T-shirts. Layer-up with coats and boots, or keep it cool in a light top. Experiment with colour, print or fuss-free design in a daytime skirt and top outfit.
● Pencil skirt and top combinations for nighttime include; pencil skirts and tops in dressier fabrics like leather, lace or sequins. Tops to wear with pencil skirt outfits at night need to be either structured or delicate.
● Pencil skirts and tops are an essential part of any professional wardrobe. Tops to wear with pencil skirt in this scenario need to be polished and chic. A white or colorful pencil skirt can upgrade a skirt and top outfit.
● Invest in and trial different tops for pencil skirts; make the most of the garment’s versatility, and don’t underestimate the power of accessories. Use shoes, jewellery and belts that best suit the occasion (see the video below for more ideas).

Who knew you could do so much with the humble pencil skirt! Versatile and timeless, get inspired to create your dream pencil skirt outfit. Are you ready to write the next stage of your fashion journey? Read more great articles on women’s fashion here at alexie