Outfits with Pencil Skirt-40 Best Ways to Wear Pencil Skirts

What to Wear with Pencil Skirts- Pencil skirts are slim-fitted skirts with a straight and narrow cut. They could be knee-length or longer, but no matter how long or short they are, they undeniably are a timeless gem. They work whether you’re going to grab a cup of coffee with a friend or simply getting ready

for a meeting at work. They are chic and feminine, which is why every woman loves them.

No matter what your age or size is, pencil skirts always look classy on a lady, so read on for 40 beautiful outfit ideas with different types of pencil skirts, along with some great tips and even a video tutorial to help you master this skirt.

How to Wear a Pencil Skirt


Let’s start with the dos and don’ts of wearing pencil skirts:

  • If you have an hourglass figure, do wear pencil skirts with a shirt tucked in or with a crop top as this will highlight your slim waist.
  • Don’t tuck your shirt in the pencil skirt if you are wider around the hips or have an apple-shaped figure. Instead, opt for tops that are looser and longer in length.
  • Don’t wear high-waisted pencil skirts if you’re petite. Instead, go for mid or low-waisted ones.
  • Always buy pencil skirts with the right fit and length, so you feel at ease when wearing them.
  • Don’t wear printed skirts with printed tops.
  • To keep it office or school-friendly, buy knee-length pencil skirts.
  • Avoid wearing striped pencil skirts with animal prints.
  • Pastel colored pencil skirts are best for Spring.

what to wear with pencil skirts


↓ 40 – Pencil Skirts for Women Over 40

Whether you’re over 40, 50, or 60, pencil skirts will continue to be your best friends and help you age gracefully. You should also have a look at these 20 Best Dressing Styles for 40 Plus Women.

pencil skirt outfits for 60 plus women

Viapencil skirt outfits for 50 plus women

Viapencil skirt outfits for 40 plus women


↓ 39 – Plaid Pencil Skirt Outfit for Winters

pencil skirt outfits


↓ 38 – Carnival Outfit in Pencil Skirts

Slay at the winter carnivals in your gorgeous pencil skirts. Here are some more Girls Carnival Outfits Ideas.

pencil skirt outfits


↓ 37 – Elegant Outfit in a Midi Pencil Skirt

pencil skirt outfits


↓ 36 – How to Wear Pencil Skirts Modestly

You should also try these 20 Gym-wear Ideas for Modest Look.

pencil skirt outfits

Viapencil skirt outfits

Viapencil skirt outfits


modest pencil skirt outfits


↓ 35 – Pencil Skirts with Boots

Pencil skirts undoubtedly look best with ankle boots.

how to wear pencil skirts


↓ 34 – Pencil Skirt Look for Weddings

An olive green pencil skirt paired with an off-white or cream-colored blouse will be the ideal outfit for guests in this wedding season. You can find more ideas from these Outfits to Wear for Vineyard Wedding.

women pencil skirt outfits


↓ 33 – Pencil Skirt Outfit for Work

Here’s a classic work outfit for women with some sleeve drama, as statement sleeves are trending more than ever now.

women pencil skirt outfits


↓ 32 – What to Wear with Pencil Skirts Casually

For casual wear, pair your pencil skirt with a crop top, and for the hairstyle, go with a messy top bun. Here are 20 Cute Outfits with Top Bun Hairstyle to Compliment Style

pencil skirt outfits


↓ 31 – Pencil Skirts with a T-shirt

how to wear pencil skirts


↓ 30 – How to Wear Pencil Skirts if You Have a Belly

If you’re heavy at the waist, avoid tucking your shirts in with pencil skirts. Instead, go with loose and flowy tunic tops that are slightly longer in length. Here are 20 Stunning Skirt Outfits Combinations for Plus Size Ladies.

how to wear pencil skirts


pencil skirt outfits


↓ 29 – Cute Shirts to go with Pencil Skirts

The cutest shirts to go with pencil skirts right now are ones with ruffles or statement sleeves.

different ways to wear pencil skirts

Viadifferent ways to wear pencil skirts

Viadifferent ways to wear pencil skirts


↓ 28 – Pencil Skirts with Flat Shoes

When it comes to flat shoes, sneakers are the best option to go with pencil skirts. They’re particularly recommended for traveling as sneakers make all your travels much more comfortable. Here are the 18 Best Sneaker Styles for Girls this year.

pencil skirts with sneakers


↓ 27 – Wearing Pencil Skirts to Church

Here are some modest but chic outfits with pencil skirts that can be worn to the church.

pencil skirt outfits

Viapencil skirt outfits


↓ 26 – Pencil Skirt Outfit for Plus Size Women

Always remember that dark colored pencil skirts are more slimming than lighter ones.

pencil skirt outfits for curvy girls


↓ 25 – Go Monochrome

Get the perfect cute and flirty look by pairing a black and white striped pencil skirt with a cutout top and silver pointed-toe pumps!

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↓ 24 – Yellow It Up

When going for a bright yellow skirt, take it up a notch by pairing it with a yellow bag and a yellow bandana. With the addition of a funky top and cuff bracelets, you’re ready to turn some heads! Here are 27 Ideas on How to Wear a Yellow Skirt.

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↓ 23 – Keep It Simple

Whether going out with friends or simply running some errands around town, keep it simple by going for a black crop top and black accessories with an adorable checkered knee-length skirt.

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↓ 22 – Chic In Neutrals

Who said neutral colors are boring? Grab your go-to white button-down with a tan pencil skirt and nude heels for that classy day look. Don’t forget the leopard print clutch for the extra edge!

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↓ 21 – Date Night in Pencil Skirts

Looking for a way to take your plain black skirt to the next level? Pair it with a red top and black accessories, and you’re ready for your dinner date! Here are 20 Best Outfits to wear on a Date.

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Step by Step Video Tutorial on How to Wear Pencil Skirts in Different Ways

↓ 20 – Day-Time Lace

Lace skirts are often worn at night since they are considered a bit formal. To make it daytime casual, all you need is a grey t-shirt and you’re good to go! Here are 28 Ideas on How to Wear Stylish Wrap Skirts.pencil skirt outfit ideas 6

↓ 19 – Tribal Prints Done Right

Not sure how to pull off your tribal print skirt? A plain white top and white heels are all you need!

Tribal Prints Done Right


↓ 18 – Winterize your Pencil Skirts

Be your own stylist and see which patterns go together. Pair a striped skirt with polka dots and let the magic unfold! You should also see these 27 Ideas on How to Wear Orange Skirts.

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↓ 17 – Flawless In Leather

Knee length skirt and a graphic T-Shirt. Looking flawless was never this easy.

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↓ 16 – Over-Sized Sweater

Looking for comfort AND style? An oversized sweater and a deep navy blue pencil skirt is the way to go. Modern chic done right! Here are 18 Best Styles of Sweater for Women this Year.

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↓ 15 – How to Wear Pencil Skirts with Leggings/Tights

Here are some ideas on wearing your pencil skirts with stockings, leggings and tights.

how to wear pencil skirts with leggingshow to wear pencil skirts with leggings

Viahow to wear pencil skirts with stockings

Viahow to wear pencil skirts with tights


↓ 14 – Play With Textures and Prints

Make a bold patterned pencil skirt work for you by keeping everything else black and simple.

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Create an outfit with one dominant color like burgundy or navy, while mixing with different textures. For some more amazing ideas, you must look at the Amazing pencil skirts collection for women.

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Or go for a funky look with an artistic and colorful top, paired with a black or grey pencil skirt. It looks awesome on redheads for sure.

how to wear pencil skirts


↓ 13 – Flirty In Plaid

If you’re not ready to give up on your plaid button-down just yet, turn it into a flirty outfit with heels and a black pencil skirt.

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↓ 12 – Navy Blue Horizontal Stripes

Keep it classy with a navy striped skirt and beige accessories. You should also have a look at these 10 Ways to Wear Striped Shirts.

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↓ 11 – High Street Fashion Look

It’s time to pull out that unusually patterned skirt from the back of your closet and pair it with a poncho-style top, to get this effortlessly chic look.

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↓ 10 – Cute in Blues

Bring a new meaning to ‘Monday Blues’, by mixing light and dark blue hues for work. With the addition of statement jewelry, give the outfit the edge it needs. Here are 25 Ways to Wear Cobalt Blue Skirt.

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↓ 9 – Slay In Suede 

Don’t hesitate when reaching for a suede pencil skirt, as long as it’s the perfect fit; you’re ready to slay!

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↓ 8 – Hot Casual Friday

A chambray blouse and a perforated floral designed skirt for a casual day at work are perfect. And if you’re comfortable in heels, go for black leather mules. Also, have a look at these beautiful Ideas How To Wear Mules Shoes.

Casual Friday

↓ 7 – Pop Of Color for Fall

When keeping it simple with a black and white striped skirt and white blouse, add a pop of color by wearing bright red shoes and a matching lip color.

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It’s hard to create an outfit for work that is both stylish and chic. This knee-length grey skirt and maroon top help you check both the requirements while going well with the Fall palette.

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↓ 6 – The Professional Suit with Pencil Skirt

pencil skirt suit outfit


↓ 5 – Check Print Skirt for Work

Add a blazer and t-shirt with your check print skirt, and you can pull this off as a day AND evening look. Also check out 10 matching outfits to wear with pencil skirts for A chic look.

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↓ 4 – Pencil Skirt Colours for Winters

Peach, Grey And White are perfect for the cold Winter days. When going for a light colored outfit, add texture with a lace skirt and shiny silver heels.

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↓ 3 – The Hearty Look for Valentines Date

Heart patterned shirts and accessories are not just for Valentine’s day. Wear this all red outfit for a fun day out with friends.


↓ 2 – How to Wear Pencil Skirts in Summers 

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↓ 1- Plaid And Leather

Don’t be shy when opting for a skirt with a slit. Wear it with confidence and sunglasses for a day out in town.

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