How to Wear a Pencil Skirt

Pencil skirt outfits are flattering, fabulous choices for women of any size. They’re always in style and exude elegance, making them perfect for the office or date night. Yet their tight fit and upscale appearance can make them intimidating if you don’t know what else to wear. In this article, we’ll discuss the different types of pencil skirts and what to match with them.

Plus size model in pink top black skirt, black pumps and silver purse

Shopping for the Right Skirt

Go for Fit First

As with any type of clothing, fit is exceptionally important. You want a pencil skirt to fit over the widest part of your hips without cinching in your stomach. If necessary, buy a size up and have your skirt tailored to fit your proportions.

Decide on Shapewear

There’s nothing wrong with shapewear to give your body a smooth silhouette! You’ll want to wear a body suit, body control dress, corselette, shaping camisole, or other piece that covers both your waist and hips. This way, the area around the top edge of the skirt won’t pucker or pull in an uncomfortable way.

Smiling woman in a beige cable-knit sweater and black skirt, walking confidently against a soft, neutral background.

Choosing a Pencil Skirt

“The color, pattern and texture of your pencil skirt make all the difference.”

Although they all have the same basic look, the slight differences between skirt styles can make all the difference.

Traditional

A traditional pencil skirt starts right at or below your natural waist and ends at or below the knees. Traditional skirts are classic and timeless, and they should be in every woman’s closet.

High-Waisted

High-waisted pencil skirts start inches above your natural waistline, sometimes coming all the way up to the bust. They’re a favorite of plus-size women for their flattering, body-shaping capability: They both enhance and create the illusion of an hourglass figure. However, they’re made to be worn with a tucked-in shirt.

Patterned

Most pencil skirts come in solid colors or simple business patterns like pinstripes. That said, you can still find skirts in a variety of patterns. Large floral prints are a popular choice, but don’t be afraid to seek out an animal print like leopard or zebra. You may even be able to find a fake snake- or alligator-skin skirt.

Because pencil skirts take up more of the body than tops or tights, you’ll want to be less flashy with your other articles of clothing so things balance out. You can still wear a patterned top, but make sure it isn’t as eye-catching as your skirt.

Embellished

Trim, ruffles, and lace overlays are all ways to jazz up a typical pencil skirt. Some will have ruffled edges or seams that add to the outfit’s femininity. Others may flare out slightly at the bottom, falling somewhere between a pencil skirt and a mermaid skirt.

You can also find skirts paired with an oversized belt. This enhances the skirt’s hourglass-shaping nature and adds a pop of interest to any piece.

Woman in a fitted pink top and black pencil skirt, standing confidently with hands on hips against a neutral background.

Outfits with Pencil Skirts

“Pencil skirts are best worn as part of a professional or formal outfit.”

That is because they’re a more classic piece of clothing, pencil skirts are best worn as part of a professional or formal outfit. Pull them out for an office presentation or for date night at an upscale restaurant.

Need some ideas? Here are a few suggestions for how to wear a pencil skirt:

Skirt Suit

If you need to pull a power pose at work, a pencil skirt suit is the perfect finishing touch. Look for one with classic business elements like dark neutral colors, pinstripes, and a formal matching blazer. Small earrings and a simple necklace will complete the look.

Plus-Size Pencil Dress

If your office’s dress code is a little more forgiving, you can wear a plus-size pencil dress. These are available in a variety of colors, and color-blocked bright tones are particularly stunning. Pencil dresses are also great for an upscale date to your favorite theater or sushi place.

Tops that Flatter

“A classic button-down shirt tucked into a pencil skirt is a great office look.”

You have lots of options when it comes to your upper half. You can continue the figure-hugging look with a tight 3/4-sleeve shirt or sleek tank top. Throw a blazer or cropped jacket on top and you’re ready to go!

Or, you can go loose and flowy on top and tight on the bottom for an interesting visual contrast. Try billowy kimono-style sleeves, an empire waist or a short tunic top.

For the office, a classic button down tucked into the skirt is perfect.

woman wearing sleeveless white blouse, tropical pencil skirt and ankle tie heels

Shoes to Wear with Pencil Skirts

A classy skirt deserves a classy pair of shoes to go with it. Pumps and pencil skirts are always a great pair, and you can have a lot of fun experimenting with patterns.

Many people consider animal print to be a neutral now, so why not pair leopard-print pumps with a bright pink pencil skirt?

Flats are also a great option if you’re more practical. Both pointed and round toes work well, and again, play with embellishments like patterns and gold buckles.

When it comes to sandals, fancy or heeled ones work better than casual flip-flops. Try heeled strappy sandals in a metallic tone or wedges with braided hemp on the heels.

Two pairs of high-heeled shoes, one in burgundy and the other in black, displayed on a gold background.

Amazing Accessories

Because pencil skirts contour the body, experiment with accessories that add volume or create interesting silhouettes. Try a bulky infinity scarf (opt for a thin fabric in the summer and knit wool in the winter) or a fabulous hat.

You can also experiment with statement jewelry, especially if the rest of your outfit is in solid colors, neutral tones or small patterns.

Feeling Fabulous in Your Outfit

Everyone looks good in a pencil skirt, no matter what their size! The silhouette is made to enhance a woman’s curves, and the length makes everybody look tall and gorgeous.

When choosing a pencil skirt, it’s important to select styles that make you feel great. You don’t have to stick to a navy business type if that isn’t your thing. There are plenty of colors, patterns, accessories and trims to choose from.