How to Wear a Pencil Skirt and Look Amazing

Thalita Ferraz // Last Update: September 17, 2022 // 0 Comments is reader-supported. When you buy through links on my site, I may earn an affiliate commission.  Learn More

I watched a girlfriend throw out a pencil skirt the other day. Well, she tried. Her reasoning was that it was a work skirt, and she didn’t need it for work anymore; therefore, it was just taking up room in her closet. 

After the shock wore off, I helped myself through her wardrobe and picked out a handful of different outfits that looked stunning with her pencil skirt to show her exactly why she should NOT get rid of it.

And guess what? She didn’t end up tossing it. So, as a woman that loves clothes as much as I do, I felt I needed to protect any pencil skirts that may be in your wardrobe that need loving.

Best Places to Buy a Pencil Skirt

Our Favorite: Topshop | Luxury Option: Revolve| Budget Option: Zaful

How to Wear a Pencil Skirt for Work

Pencil skirts are great fashion pieces for work because they’re simultaneously modest and flattering. Unfortunately, some work attire isn’t the most fitted or feminine, so these skirts are excellent ways to stay covered, while looking work appropriate and cute or sexy!

This first outfit is super slimming and unpretentious, while being subtly fashionably forward. Her tweed skirt isn’t a pattern often worn outside of the business place, usually because of it’s thick material. She did great pairing a green sweater with small ruffle accents and a deep burgundy pair of velvet heels with it! 

The second outfit is stunning with a more flirty desert sunset palette. Her camel colored skirt is perfect with a tucked in black chiffon top. The addition of the crisp white blazer adds a professional touch, while her matching bag and nude pumps up the sexy!

How to Wear a High Waist Pencil Skirt

High waist clothing never fails us, and with pencil skirts, they usually offer a little extra support up there if needed. Who could complain about that, right? 

In this first image, we see Emily Ratajkowski, a fashion icon that’s no stranger to the big screen. She’s wearing this amazing, velvet, high waist, pencil skirt with a cropped, turtleneck tank top to show some skin. Adding to the sexy factor, she’s wearing metallic strappy heels, which help elongate the look of the leg.

You could easily tone down the look and still show skin by wearing a cropped t-shirt with a high waist pencil skirt. 

In this second outfit, she’s wearing a black, shorter, high waisted skirt with a green, short sleeved tee tucked into the front. It’s not really a dressed up look, but the addition of her chunky statement necklace does wonders for it!

What kind of shoes would you wear with this? Depending on what I’m doing that day, I’d either wear a pair of black heels or a pair of black flats. You could easily wear sandals or even sneakers with this too!

How to Wear a Pencil Skirt with Sneakers

Sneakers are a girl’s best friend. Really, they can be made to work with so many outfits, so of course, I had to show you a couple of cute ways to wear a pencil skirt with sneakers.

When you initially glimpse at this first outfit, you’d never imagine she’s wearing a pair of old vans with it. It’s so edgy, and I love the zipper detail down the front of her pencil skirt. 

You could easily add any plain or graphic tee with this and tuck it in like she did, just like you could wear whatever favorite pair of sneakers you have. 

This second outfit though! Isn’t it stunning? Her chocolate pencil skirt is amazing with this oversized taupe/ gray sweater that is partially tucked in. 

Had you not seen her shoes already, what do you think she’d be wearing? Heels maybe? But surprise! These sneakers look amazing with her outfit, and it helps dress it down a bit. 

If these are not proof that sneakers look great with skirts, I don’t know what is!

How to Wear a Pencil Skirt Casually

I love when clothes that would otherwise be formal can be worn casually. This is a great trick, too, that can help prevent having too many clothes, if there is such a thing. Having pieces that can be dressed up and down are the best!

So take a look at this first outfit! I really love a good, denim jacket. You can see one of my favorites here, in this Zara Jean Jacket with Pink Dress outfit

All she has done, is pair a gray, heathered, pencil skirt with a white tee or tank and draped a denim jacket over top and added a pair of gray sneakers. Super easy, anyone can do it. I’d love to even see a baseball cap added to this.

This second outfit is a cute and casual one, with an adorable floral printed pencil skirt! If you were buying this floral skirt, where would you be wearing it to? Me? I’d buy it for a semi-formal event of some sort.

But then when do you wear it again? THIS IS HOW. You add a plain v-neck or crew-neck tee with it and viola! Plus, her heels are great, but you can absolutely wear sandals or even sneakers with it.

How Plus Sized Girls Can Wear a Pencil Skirt

I love this first outfit. Her color pallet is on point for a perfect fall look. Remember me saying how pencil skirts help support us in places that we all love to be supported? This is it, ladies. 

Don’t be afraid to wear the fitted skirt and shirt! Your curves are beautiful, as is this outfit. I love the addition of her green blazer or cardigan with the tan skirt and flats. It adds this pop of color to the rest of the neutral colors in her scarf and bag. 

This second outfit plays with bell sleeves, which is so fun. Her blouse is a flowy one that covers the top of her black pencil skirt, but she enhances her curves by adding a belt around her waist. Those red velvet heels too, aren’t they great? They pull the red from the flowers on her blouse. 

Also, a fashion tip! Vertical stripes more slimming than horizontal ones.

How to Wear a Pencil Skirt in Winter

This first outfit may not really be a good one to wear to play in the snow, but it definitely is a good one if you’ll be indoors during the winter!

She looks like she stepped off the runway. Which is wild, because it’s a really simple outfit with three main items: an oversized turtleneck sweater, a pencil skirt, and ankle boots. 

If you’re concerned about your legs being cold, a pair of black or even patterned tights can be worn with this. The fall/winter fashion forecast is predicting patterned tights being big for the 2019 season!

This second outfit, excuse the mirror selfie, but isn’t it gorgeous? She’s so color coordinated, her fingernails match her skirt. To be on that level, is just… fashion goals. 

So let’s talk about this. She’s wearing an oversized sweater tucked into her white pencil skirt with knee high boots. I wanted to show this one, not only because it’s stunning, but because she’s killing it with the boots! You can add boots like these with a pencil skirt so easily.

If you’re wearing an outfit like this during the winter, it would be amazing to drape a peacoat over the shoulders, or even wear a trench coat. A coat like this Camel Coat I’m wearing this OOTD would be perfect. 

I hope that after reading this post, you’re loving pencil skirts as much as I do. I really couldn’t believe that my girlfriend thought they were only for work. 

I understand, though. I have worn mine mostly for work and I have one that is lacy and strictly for, “going out,” so I could use some improvement on wearing mine more regularly. I’m inspired though, aren’t you?

We both had a refresher on how to wear them for work, with sneakers, casually, in winter, and how curvy ladies can confidently rock them!

So now, let’s you and I chat. Do you own a pencil skirt? If no, are you interested in getting one? If yes, is it for work? For play? 

What was your favorite way to wear a pencil skirt? Tell me in the comments below!

Best Places to Buy a Pencil Skirt

Our Favorite: Topshop | Luxury Option: Revolve| Budget Option: Zaful

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