20+ easy ideas to style a black pencil skirt

A black pencil skirt is a wardrobe essential. It is simple enough to be worn on it’s own and to be styled multiple different ways. It easily transitions from day to night and throughout different seasons.

Pencil skirts are flattering on all body types there are so many styling possibilities! The higher waist fit helps to highlight Nautral curves and give you an hourglass figure.

I love dressing up pencil skirts for work events and even date night but there are so many ways to style it casually as well! Here are 20+ ideas on how to wear a black pencil skirt!

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How to wear a black pencil skirt:

These pencil skirt outfits can be worn for so many different occasions. The best part of these outfits are that they are not complicated at all, you start with a straight skirt and different tops and you’ve got so many outfits to work with!

ideas on how to wear a pencil skirt

Black pencil skirt outfits for all body shapes

These styles can be worn for women of all ages and all body types. If you on the shorter side and looking how to style for a petite frame, you can look for petite skirts that run a bit shorter (hits above the ankle) or even add a top over a slim dress to create the same look.

#1 Denim Shirt

Along with the pencil skirt, a chambray shirt is a wardrobe essential! Pair them together and you have a perfect match to take you from day to night.

I love it paired with the leopard heels and it is so cute with a camel colored coat overtop for a pop of color. This is a great look for Fall/Winter or you could do a shortsleeved denim top for Spring/Summer.

denim shirt, pencil skirt, blazer
(Photo Source)

#2 Simple White Blouse

I love the idea of a crisp white shirt with a long pencil skirt. This is a classic piece that you likely already have in your closet and when paired with a tight pencil skirt it is super flattering and perfect for work or even date night.

The sleeves on the tops shown add a nice feminine and flowy detail that really complements the tighter fit of the pencil skirt.

#3 Plaid/Flannel Shirt

Pairing a pencil skirt with a plaid shirt is such an effortlessly fun way to style it. I love this combination and how she knotted it below to show her lace top underneath – so cute!

It’s really easy to work with different top combinations and with the right accessories you are set for work to happy hour!

You could also wear a flannel shirt buttoned up and tucked into the skirt or an oversized flannel left open over a crop top! The possibilities are endless.

#4 Layered Sweater and Collared Shirt

This is a great option if your work in a corporate office setting. Layering a pullover sweater over a button down shirt is so chic and ultra stylish.

You could do this with neutral colors or even pair a printed button-down underneath a bold colored sweater for a fun look.

The simple shirt paired with the midi pencil skirt is great for a straight to a pear shaped body type.

black pencil skirt outfit
(Photo Source)

#5 Simple Pullover and Sneakers

For a casual pencil skirt outfit, pick your favorite cozy oversized sweater and sneakers and you’re good to go to grab lunch!

This is another effortlessly cool way to style a typically more preppy/put together skirt. I find stretchy pencil skirts to be really comfortable so I would be more than happy running errands in an outfit like this.

#6 Knotted T-shirt and Booties

Knotting a simple t-shirt is a great way to amp up simple basics. I love it paired with nude booties for a cute fall look.

This knotted technique would look great with a graphic tee, tie-dye tee or tank top as well.

The long black skirt with the slit is great as it also makes it easier to walk in! Both of these are a staple piece that you’ll wear a lot with other pieces as well.

It’s the perfect casual look if you wear it with sneakers and add a baseball cap!

casual tee with pencil skirt
(Photo Source)

#7 Sweatshirt and Heels

Dress up a sweatshirt with a faux leather pencil skirt and heels!

I love this way of styling a pencil skirt because it feels put together and not too forced. This would be another outfit that would be totally great to wear to the office or even if you work from home! Comfortable but still put together.

I’d love this styled with a chic wool coat and scarf for cooler months as well.

casual sweatshirt with slim skirt
(Photo Source)

#8 Add a belt

The use of belts really helps to accentuate your natural curves or give you the illusion of curves. The belt really accentuates the flattering fit of the higher waist on a pencil skirt.

When styling with a belt I would stick to more neutral colors overall and let the belt be the focus. I love the oversized gold buckle as shown in the inspiration photo below.

This would also be cute if you have a designer belt that you want to showcase!

skirt and belt outfit
(Photo Source)

#9 Graphic Tee

Graphic t-shirts can be styled in so many ways, and with a pencil skirt is no exception! This is the perfect Fall outfit.

I love it with the cute little bag and the pointed toe suede booties as shown in the photo below. This would also be really cute with a faux leather pencil skirt.

#10 Silky Cami

A silky cami really elevates a black pencil skirt. Top it with a blazer for office wear and on it’s own for a cocktail party. This would also be great if you had a bodysuit with this type of silky material to pair with the pencil skirt.

date night pencil skirt outfit
(Photo Source)

#11 White Tee and Denim Jacket

This is one of my favorite ways to style a pencil skirt! So easy and you likely already have all of these items in your closet.

Just choose your favorite white tee/tank and go-to denim jacket. Add heels, boots, flats, sneakers or whatever else fits best for your occasion and you’re good to go!

white tee and denim jacket with pencil skirt
(Photo Source)

#12 Monochrome

Pairing a black pencil skirt with a top, coat and shoes in the same color is so chic! This is a street style look that is easy to replicate and really is stylish.

I love the cozy gray sweater and chic gray coat paired with fun gray sneakers. You could also do this with a camel colored sweater, coat and booties for a cozy Fall look.

gray coat and skirt
(Photo Source)

#13 Peplum Top

Peplum tops are so flattering and when paired with a pencil skirt is really gives you an hourglass figure. I love the feminine aspect to a peplum top and it is a nice contrast to the body hugging pencil skirt.

#14 Black Tee

Pairing a black tee with a knee-length pencil skirt almost gives the illusion of a little black dress! This is so chic and depending on your jewelry and shoes could easily be styled for day or night and different occasions.

Simple black heels and pretty gold jewelry make this perfect for the office during the day and drinks at night.

black tee and pencil skirt
(Photo Source)

#15 Black Turtleneck Sweater

I love wearing turtlenecks in the colder weather and I think they look so pretty paired with a pencil skirt. Just add some nude heels and you’re good to go for the office or happy hour.

turtleneck sweater and pencil skirt
(Photo Source)

#16 Trench Coat

Pairing a trench coat over a pencil skirt is another one of my favorite ways to style it! It looks so chic (I love the olive color in the inspiration photo shown below) and is great for Fall coming up. It would also be cute with a crop top underneath the trench coat!

#17 Cardigan and Knee High Boots

A great option for the modern fashionista – wearing a cardigan all buttoned up as a top and pairing with knee high boots.

leather pencil skirt
(Photo Source)

#18 Floral Blouse

A floral blouse is something you typically already have in your style and it adds feminine little details and a pop of color to a simple pencil skirt!

The possibilities are endless with floral blouses just based on the silhouette of the various tops – I think an off the shoulder style would also be so pretty!

You could also pick polka dots or stripes as a fun print with the pencil skirt if the floral option isn’t your style!

#18 Knotted Button Down and a Hat

I love the idea of doing a knotted button down for an effortless feel with a pencil skirt. As seen below, she styled it with simple scrappy heels and a cute hat! This would be a great outfit to transition into Fall weather.

long skirt with slit
(Photo Source)

#19 Leopard Print

A classic print like leopard is the perfect match for a black pencil skirt. Just add your favorite high heels for a sleek office ready look.

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#20 Florals for work

A classic combination for work. Just pair it with a classic pencil skirt and you’ve got a flattering and chic outfit. This is also a great outfit to look chic for the winter and not freeze!

Need more style inspiration? Don’t miss the below!

How to build a winter capsule wardrobe

The Best Dresses for Petite Women

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