What to Wear With a Pencil Skirt – Style Tips & Outfit Ideas

What to Wear With a Pencil Skirt - Gray pencil skirt and gray striped shirt outfit - Visit Stylishlyme.com for more outfit inspiration and style tips

How to Wear a Pencil Skirt

If you’re looking for a flattering and versatile skirt for the office, I would have to suggest the pencil skirt. This classic skirt works for all shapes and sizes and when paired with the right blouse and accessories will always look stylish.

You might be wondering what to wear with a pencil skirt—and there are a variety of ways a pencil skirt can be styled—but today we’re going to discuss how to wear a pencil skirt outfit to work.

If you are new to pencil skirts and wondering what to wear with a pencil skirt, let’s begin with the basics…


Fit and length are the two most important details that you must pay attention to when it comes to the pencil skirt. A pencil skirt tends to be most flattering when the hem ends around the knees. It can be slightly above or below but not any shorter.

The skirt should be fitted around the waist and skim over the hips. If the waistband is a bit too snug and you find it difficult to sit, then it’s too tight. Another telltale sign of a poor fit is if you see horizontal lines develop across the hip area.

By combining the right length and fit, you’ll find that the skirt will gracefully follow your natural curves and be comfortable to move and sit down in. Fit is critical for work—so make sure the length and fit are perfect so you feel stylish and confident. You shouldn’t have to fuss with your clothes at the office because what you need to be focusing on is the work in front of you.

NOTE: Most pencil skirts come with a slit, which allows you to walk more freely and sit easier. They can be located in the back, on the side, or the front. Be conscious of how high that slit is since you will be wearing your pencil skirt outfit to work.


Pencil skirts can be paired with a feminine blouse or a more masculine shirt, depending on your style and the skirt itself. When choosing a pencil skirt, you can opt for simple with a solid-colored or pinstripe straight skirt. This allows you to pair it with a blouse that has color, detail, interesting neckline, or embellishments. If you prefer to move the attention away from your waist or hips, this is the best style for you.

Alternately, you can look for a skirt that has some wonderful details or a bit of character—a vertical line of buttons, a ruffle, waist detailing, or accent pleats. In that case, you would pair the skirt with a simpler blouse or shirt. This styling works well on bustier figures or those without curves.


A sheer blouse paired with a pencil skirt can take you from the office to an evening out. The trick to remember is to pair the blouse with a tank that is similar in color. The color of your undershirt is very important because you want it to be understated and color coordinated. If you were to wear a white sheer blouse with a navy blue undershirt it would stick out like a sore thumb—nothing subtle about that. The look you’re going for when wearing sheer blouses to the office: subtle, modest but modern, and stylish.

Because the blouse is sheer and flowy, it is where the attention is focused, so you can pair this with a simple pencil skirt in either a solid or a subtle pattern, like this black-and-white pencil skirt outfit I am wearing. While I paired it with some neutral heels, I did add a pop of color with the red purse. Perfectly stylish for the office!

Patterned Pencil Skirt for the Office - Visit Stylishlyme.com for more outfit photos and style tips


Peplum tops are a perfect match for a pencil skirt. The flair of the peplum over the waist and hips is a nice contrast to the straight line of the skirt and does a good job of accentuating your waist and hiding hips.

Because of the peplum, be sure to choose a skirt without any detailing, as it will push the outfit over the top and inappropriate for work. Stick to a simple solid or thin pinstripe skirt. The peplum top can be a solid or pattern. In fact, black on black looks good with this pencil skirt combination. Add a pop of color with your heels and purse and you are good to go.


I love the detailing on the skirt in this picture. While the color of the skirt is a simple charcoal gray, the ruffle along the side adds so much character. Similarly, you could find a skirt with a tuxedo stripe, a row of buttons, or other embellishment to add some drama and flair.

When wearing a detailed pencil skirt, pair it with a simple top. I’m wearing a simple sleeveless button-down in a bright color that compliments the skirt. You could opt for a simple long-sleeve silk blouse or even offset the skirt’s femininity with a cotton button-down Oxford shirt. A pair of pumps, slingbacks, or even sandals in a neutral similar to your skirt color finishes the outfit.

Black Ruffled Skirt


In this outfit, I paired a gorgeous gray pencil skirt with a striped button down with contrasting cuffs. The thin vertical lines in the skirt look great against the thicker, bolder stripes on the blouse. When combining two striped pieces such as this, make sure the stripes are different in size, as it will keep the outfit from looking too crazy and busy. (You could also wear a solid color menswear-inspired shirt with a high-waist pencil skirt like this.)

As you can see from the photo, the gray color palette, and vertical lines help to elongate my figure by creating nice long lines. To keep this outfit from looking “stuffy,” I rolled up my shirtsleeves and had the dark cuffs peeking out for an extra touch of attitude.

The finishing touch for this wear-to-work look: leopard heels. The leopard heels help add pattern, color, texture, sexiness, and attitude to this stylish at work outfit. Yes a pair of heels can add so much to an office outfit!

NOTE: High-waist skirts can be difficult for you shorter girls. When choosing this or other pencil skirt, be conscious of where the top of the skirt hits you and that the waistband is not sitting too close to the bust line.

Along with answering what to wear with a pencil skirt I wanted to share a few things you should have in mind when it comes to fit.


If you wear a high-waist skirt or a skirt with a thicker waistband, then a blouse would look best tucked in.

Personally, I always wear my shirts tucked in when wearing a pencil skirt. There are many positives to wearing your shirt tucked in: it creates a slimmer waist, makes the look more sophisticated, which is especially appropriate for the office, and for the petite gals (like me) it creates the illusion of longer legs.


On another note, I feel like I need to share this because some mornings you may feel the same way.

Getting ready every morning can feel like a chore. Especially when you feel like you have nothing to wear, that’s the worst. Getting dressed in this gray outfit the other day was hard! My love affair with clothes doesn’t make me immune to feeling like I don’t know what to wear and I get a bit frustrated when I can’t seem to put together a decent outfit.

But when you don’t want to “dress nice” is when you especially need to. Remember, “you’re not always going to feel like it but successful people do it anyway.” After huffing and puffing about not knowing what to wear I ended up putting together this very stylish outfit for the office. I know there are many other important things going on in the world but when you feel put together you are more confident and are able to take on anything!

Don’t take getting dressed in the morning lightly because it sets the tone for the rest of your day! If you need some tips on how to look stylish every day make sure to read this post: How to Look Stylish Every day – Your 5 Step Checklist.

I hope this answers your question on what to wear with a pencil skirt!

Stay Stylish,

What to Wear With a Pencil Skirt  - Visit Stylishlyme.com for more outfit inspiration and style tips

Stylish outfit for the office - Visit Stylishlyme.com for more outfit inspiration and style tips

what shirt to wear with a pencil skirt - Visit Stylishlyme.com for more outfit inspiration and style tips

Striped professional shirt with dark cuffs - Visit Stylishlyme.com for more outfit inspiration and style tips

What to Wear With a Pencil Skirt - a stylish all gray look - Visit Stylishlyme.com for more outfit inspiration and style tips

wearing a striped button-down with a pencil skirt - Visit Stylishlyme.com for more outfit inspiration and style tips


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