Pencil skirts are a closet staple. Here’s how to wear them in casual outfits.
These slimming pencil skirts are commonly worn for work, but you can also wear them in cute casual outfits too.
Pencil skirts also come in all types of materials, styles, and colors, so there are plenty of versatile options to choose from.
If you’re looking to dress down your pencil skirt, I’ve got tons of tips and inspiration for you!
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Casual Pencil Skirt Outfits
There’s no doubt that pencil skirts are incredibly flattering. They hug your body and highlight your curves in all the right places.
A pencil skirt is feminine and sexy, which makes it one of the most empowering pieces a woman can wear. Plus, your waist and bottom never looked better. 😉
Keep reading for some chic, casual pencil skirt outfits. You don’t want to miss out on this!
Leather Pencil Skirt Outfit
There’s nothing like a cute leather pencil skirt that’ll add an edgy factor to a fall or winter wardrobe. Leather skirts are versatile pieces that bring a luxe factor to any outfit.
Plus, they can be dressed up or down for various occasions. Wear them to the office and bring them out for a fun night out.
A leather pencil skirt is versatile, stylish and comfortable. It can be worn for a wide range of occasions and is a timeless classic.
Lean into that rocker chic vibe by pairing a leather pencil skirt with a graphic t-shirt. Don’t forget to layer up with a denim jacket and complete the ensemble with ankle boots.
Shop The Outfit:
- Neiman Marcus: Marni: Logo Drawing Graphic T-Shirt
- Michael Kors: Denim Puff-Sleeve Cropped Jacket
- Hello Molly: BILLINI ZALI ANKLE BOOTS BLACK
Casual Pencil Skirt Outfit With Sneakers
A casual pencil skirt outfit with sneakers is ultra stylish and comfortable. Who can say no to a comfy pair of white sneakers? They go with everything!
To create this look, start with a ribbed knit pencil skirt with a leg slit. The leg slit makes it easier to walk in and it’s a subtle, sexy detail that shows off and elongates your legs.
Pair the skirt with a simple white t-shirt and you’re good to go! You can even layer up with a boyfriend blazer to add a bit more polish to the outfit.
Shop The Outfit:
- Michael Kors: Logo Tape Textured Knit Pencil Skirt
- maurices: 24/7 Forever Ribbed Scoop Neck Tee
- Venus: Boyfriend Blazer
Ankle Boots & Pencil Skirt Outfit
Ankle boots pair well with pencil skirts too! Try to get ankle boots with chunky heels. Not only will they elongate your legs, but they also dress down a pencil skirt outfit.
Get this look by pairing a mock neck tank top with a pencil skirt and ankle booties. Spice up your look with patterned ankle boots, such as faux snakeskin, for a pop of print in your casual pencil skirt outfits.
If you need to layer up, consider throwing on a leather jacket. A leather jacket goes well with leather ankle booties. What a vibe!
Shop The Outfit:
- maurices: Ribbed Mock Neck Tank Top
- maurices: Black Bengaline High Rise Pencil Skirt
- Venus: Faux-Leather Lace-Up Jacket
Sweater & Pencil Skirt Outfit
Chunky oversized sweaters are my go-to winter essential. They also coordinate effortlessly with pencil skirts.
Throw on a cozy oversized turtleneck sweater over a pencil skirt. Depending on the length of the sweater, you can either let the sweater drape over the skirt or do a french tuck in the front.
I recommend letting the sweater skim over the skirt if the sweater is long. If the sweater is waist length, a quick french tuck will help highlight your waist area.
Complete this ensemble with platform combat boots and this comfortable and chic look is done!
Shop The Outfit:
Denim Jacket & Pencil Skirt Outfit
Denim jackets are notoriously casual outerwear essentials. They go great with outfits in the spring and fall seasons.
Plus, they’re easy to layer on when it gets chilly and looks great with just about anything. For this look, pair a satin camisole with a pencil skirt.
The satin camisole adds a luxe detail to this casual outfit. Finally, top it all off with an oversized denim jacket.
Shop The Outfit:
White Pencil Skirt Outfit Idea
It might seem daunting to wear a white pencil skirt. However, they’re easy to style!
To create this look, pair a white cropped square-neck tank top with a white high-waisted pencil skirt. This monochrome outfit will look effortlessly classy and chic.
This outfit would look great on a tropical vacation. Just throw on a wide-brimmed sun hat and straw handbag. Now you’re ready for vacation pictures!
Shop The Outfit:
Black Pencil Skirt Outfit Idea
A black pencil skirt is a classic piece that’s incredibly versatile. You can transition them from the office to a clubbing night out.
For this casual pencil skirt outfit, here’s a fun way to dress down a black pencil skirt. To get this look, let’s embrace our feminine and sexy side with a plunging V-neck bodysuit.
Pair this with a black pencil skirt with a leg slit to make this outfit alluring. 😉 If you want to go the extra mile, choose a leather pencil skirt to spice up this look.
Now you’re ready for a fun girls’ night out!
Shop The Outfit:
How To Style Pencil Skirts
As you can see from the casual pencil skirt outfits above, there are so many ways to wear a pencil skirt casually outside of an office. It just depends on how you style them with tops, shoes, and accessories.
Plus, there’re so many styles of pencil skirts too. Play around with the colors, prints, leg slits, and materials of different pencil skirts to create new outfits.
Keep reading for more tips on what tops and shoes will pair well with casual pencil skirt outfits.
What Tops Can I Wear With A Casual Pencil Skirt?
Switching out the top is one of my favorite ways to recreate new outfits with a pencil skirt. It’s a great way to maximize the amount of outfits you can create with less pieces.
Here are some of my favorite tops to casually style a pencil skirt.
- White T-Shirt: You can never go wrong with a white t-shirt. They’re essential for a laid-back outfit. Plus, they look great with pencil skirts.
- Crop Top: A crop top is a great summer staple. Pair this with a high-waisted pencil skirt.
- Tank top: Tank tops look great with pencil skirts! These sleeveless tops will help you highlight your shoulders and arms.
- Sweater: A chunky knit sweater is stylish and makes a pencil skirt outfit extra cozy.
- Chambray shirt: A chambray shirt is a casual alternative to a typical office button-down. You can even unbutton a few buttons on the bottom and tie the ends together to create a cropped top.
What Shoes Can I Wear With Pencil Skirts?
Heels aren’t the only shoe option to wear with pencil skirts. Casual pencil skirt outfits open the doors to plenty of other cute shoe options.
Here are some of my favorite shoes to wear with pencil skirts.
- White Sneakers: Don’t have a pair? Get one. I’m serious, white sneakers are closet essentials. They go with everything and that includes pencil skirts too.
- Loafers: These preppy shoes go well with relaxed and casual outfits.
- Sandals: Sandals are summer shoe staples. These casual shoes will give your pencil skirts a more relaxed vibe.
- Ankle boots: Ankle boots are perfect for the fall season, look great with tights and can give you a polished look.
- Platforms: Platforms give you height without the heel. They’re way easier to walk in and less likely to give your feet blisters. They look amazing with pencil skirts too.
- Flats: These comfy shoes are great for daytime looks. Pair them with pencil skirts for casual outfits.
Frequently Asked Questions
What’s The Most Popular Pencil Skirt Style?
The classic slimming pencil skirt that hits right above the knees is the most popular pencil skirt style. After all, it is timeless, versatile, and suits a wide range of body types.
Pencil skirts in a neutral color with clean lines are the easiest to dress up or down. When shopping for pencil skirts, look for stretchy material and a leg slit. This will make it more comfortable when you’re sitting, standing, or walking.
Can I Wear A Pencil Skirt If I Have A Large Stomach?
Having a stomach is natural! There are plenty of ways to style a pencil skirt so that it doesn’t emphasize that part of your body. Pencil skirts can even make you look thinner.
It’s all about finding the pencil skirt that will flatter your body shape and visually direct attention away from your belly. The way you style and coordinate a pencil skirt makes a huge difference.
Read my article on how to wear a pencil skirt with a tummy. I have tips on what pencil skirt styles are the most flattering and ways to cover up a protruding stomach.
Why Are They Called Pencil Skirts?
Pencil skirts are named after their pencil-like shape. These skirts feature a straight and slim shape, similar to a pencil.
The classic pencil skirt silhouette is body hugging from the waist down to the hem. This creates a slimming illusion that draws the eye to the lower part of the body.
Christian Dior is largely credited for inventing the modern pencil skirt we know today. In 1954, he created a pencil skirt as part of his H-line collection.
What Is The Difference Between An A-Line Skirt And A Pencil Skirt?
Both the A-line and pencil skirt have a distinctive shape that makes it easy to tell them apart.
A-line skirts flare outwards from the waist area, which creates an “A” shape. In contrast, pencil skirts have a straight up-and-down cut.
If you lay a pencil skirt and an A-line skirt side-by-side, you’ll immediately see the difference. The pencil skirt has a rectangular shape and the A-line skirt has a shape similar to the letter “A.”
Their shape also affects how they fit on the body too. Pencil skirts are form-fitting throughout and often made with stretchy materials.
On the other hand, A-line skirts are fitted at the waist and flare over the hips and thighs. A-line skirts are great for hiding lower-body problem areas since it flows and flares out over them.
Pencil skirts aren’t just for the office. I hope this inspires you to dress them down and have fun with casual pencil skirt outfits. 🙂
Disclosure: Vain Affair is reader-supported. When you buy through affiliate links on our website, we’ll make a small commission, without impacting your price. Thank you. Learn more.
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