Classy Pencil Skirt Outfits

Pencil skirts are a timeless and classy edition to every wardrobe. Their elegant maxi silhouette is so versatile, allowing you to switch effortlessly from occasion to occasion. But, knowing how to style them can sometimes be a bit tricky. So today, I am excited to share a range of chic and sophisticated pencil skirt outfits to give you inspiration for your wardrobe. From a classy workwear looks, to stylish evening outfits, and even elevated daily looks, these outfits will have you feeling confident and gorgeous in your pencil skirts!

If you’re looking for more ways to style your skirts this season be sure to check out my Black Slip Skirt Outfits for Fall and my Fall Skirt Outfits for Every Occasion posts as well.

Classy Pencil Skirt Outfits

Today, I’m excited to share a variety of classy pencil skirt outfits. From formal events to casual outings, these pencil skirt looks are sure to elevate your style.

Black Pencil Skirt Outfits

A black pencil skirt is definitely a must-have in any wardrobe. This is because they not only offer a multitude of stylish outfit options, but its versatility allows you to create chic looks from this single piece. So, check out some of my favorite black pencil skirt outfits below.

Leather Blazer + Black Pencil Skirt + Boots Outfit

Classy Pencil Skirt Outfits

Black Maxi Skirt | Vegan Leather Blazer | Knitted Tank | Black Calf Boots

One of my favorite ways to style a black pencil skirt is with a monochrome black outfit. Opt for a sleek black leather blazer, a classic pencil skirt, and stylish leather boots for a versatile look that can transition from the office to date night seamlessly. This timeless look exudes sophistication and elegance, and the monochrome style is always on trend Check out more of my favorite black monochrome looks here.

Classic White Button Up + Pencil Skirt + Loafers Outfit

Classy Pencil Skirt Outfits with loafers

Black Maxi Skirt | Black Loafers | White Button Down Shirt

For a sophisticated pencil skirt look perfect for heading to the office or a business meeting, pair a white button down shirt with a classic black pencil skirt and chic loafers. This combination is not only elegant and timeless, but it is easy to style. Also, you can add black accessories or a structured blazer to complete the look, ensuring you look both stylish and professional. If you are in need of more workwear outfit inspiration, be sure to check out my post here.

Striped Knit Tank + Black Pencil Skirt Outfit

Classy Pencil Skirt Outfits with tank

Black Maxi Skirt | Knitted Tank | Black Calf Boots

If you’re looking for a more casually chic outfit, opt for a striped knit tank with a black pencil skirt and stylish boots. This combination is elevated while being comfortable. It’s an excellent choice for various casual occasions, whether it’s brunch with friends, exploring the city, or a stylish day out. Also, if you love going to brunch with friends, but never know what to wear, be sure to check out my 10 Classy Brunch Outfits for Fall.

White Pencil Skirt Outfit Ideas

A white pencil skirt is a perfect alternative to its black counterpart, offering a fresh and versatile addition to your wardrobe. There are endless ways to style this piece all year roun. So, check out some of my favorite white pencil skirt outfits below.

Lightweight Sweater + White Pencil Skirt Outfit

Classy Pencil Skirt Outfits with light sweater

White Maxi Skirt | Sleeveless Turtleneck Sweater | White Slingback Pumps

I love pairing my white pencil skirt with a lightweight sweater for those transitional weather days. Also, if you never know what to wear in that in between weather, be sure to check out my Week of Fall Transitional Outfits here. Elevate this look by opting for white heeled slingbacks, perfect for work or a chic family brunch. Or, for a more laid back outing, swap the heels for sneakers and embrace comfort.

Lady Jacket + Pencil Skirt | All White Outfit Idea

lady jacket fall outfit

White Maxi Skirt | White Lady Jacket | White Slingback Pumps

When in doubt, go for an all white monochrome outfit. It’s not only easy to style, but always timeless and classy. For this look, pair a white lady jacket with a white skirt and matching slingback heels. If the weather gets cold, simply swap out your slingbacks for sleek white boots to stay stylish. This look is perfect for anything from heading to the office or to a special event with family and friends. Be sure to check out some of my favorite monochrome white outfits for the colder weather here.

Pop of Color + White Maxi Skirt

white maxi skirt outfit

White Maxi Skirt | Pink Sweater | White Slingback Pumps

Elevating your style with a pop of color is both easy and chic when you incorporate a white maxi skirt and a colorful sweater into your look. I personally love this pink sweater, which would be so perfect for a variety of occasions. From a chic Barbie-inspired look to a Breast Cancer Awareness Month outfit, this white and pink look has you covered.

Also, for more style inspiration, be sure to check out my posts below!

Please feel free to email me at if you have any questions!  I’m always happy to help with styling or picking out a specific outfit for an event!   Have an amazing day!!

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As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


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