This post was sponsored by Cleo Madison.  All opinions are my own.  This post also contains affiliate links.  I may receive a commission if you purchase some of the items in this post.

Getting the most out of your closet is the number one tip I hope to get across as a fashion blogger.  I think building your wardrobe to have a few essential items that you can wear in a variety of ways in crucial to anyone’s closet.  Today I am sharing with you different ways to wear a pencil skirt. The black pencil skirt from Cleo Madison is one of those staple items you need in your closet because it is so versatile.  It is named the “Karli Pencil Skirt” after me! How sweet is Cleo Madison to do that? I’ve never had an article of clothing named after me, so I was pretty excited.  I love getting the chance to work with them.  I did a whole post about their perfect dresses for teachers which you can check out here.  

Chambray Shirt

View More:

While I am on the topic of closet staples, a good chambray shirt should be high on that list.  I wear this chambray shirt with so many different outfits and a pencil skirt is another great way to wear one.  I included another pencil skirt as well to show that a chambray shirt is perfect for any type of pencil skirt, making it another essential item for your closet.

Black Pencil Skirt  ||  Stripe Pencil Skirt  ||  Chambray Shirt  ||  Watch  ||  Photographer  ||  Hair and Makeup

Graphic Tee

If you are going for a more relaxed look, but still want to be comfortable in your cute, black pencil skirt, throw on a graphic tee or white t shirt and tie the ends for a fun look.

Stripes and a Herringbone Vest

View More:

View More:

Adding a white sweater with black stripes helps to tie the black pencil skirt in with your top.  I love the look of adding a herringbone vest as well for those cooler winter days.  I added a pair of grey booties and a pop of color through my purse.

Pencil Skirt  ||  Herringbone Vest ||  Purse  ||  Sweater  ||  Photographer 

Matching Top and Bottom

View More:

View More:

If you have a business meeting, interview, or want to wear a pencil skirt to church, a great place to start is a matching top and bottom set.  They are really classy and I felt like a big time, successful business woman wearing this outfit. Where are my boss babes at?

Top  ||  Pencil Skirt  || Photographer

Cardigan and Belt

Adding a cardigan over a pencil skirt is a great way to style it for any occasion.  You could wear this to church, work, and even out and about.  I wear this to teach kindergarten and it works so well because the skirt is long enough and doesn’t have any slits (which makes it easy to stay modest).  I love adding a belt as well to give it an extra fun accessory.  

Cardigan  ||  Pencil Skirt  ||  Clutch

Casual Denim Jacket and Keds

View More:

View More:

View More:

Pops of color make me a little too happy if you haven’t noticed.  So these Keds are the perfect addition to this black pencil skirt for a casual look without going too neutral.  Throw on a jacket for those fall evenings and you’ve got an outfit for running errands or lunch with friends.

Pencil Skirt  ||  Shoes  ||  Denim Jacket (similar)  ||  Necklace  ||  Photographer

I’ve also teamed up with some of my favorite fashion bloggers for our weekly series “Bloggers Fall For” where we share our favorite fall trends.  This weeks trend is braids! I had the amazing Bailey (@scheissstyles) do a five strand braid on both sides of my hair and then pin it in the back.  Isn’t it so pretty? She showed me step by step how to achieve the look so I can do it myself next time.  If you have any questions just do a youtube search for “5 strand braid” and you’ll find a lot of different tutorials! Check out how the other bloggers used braids in their posts below! 

Lindsay of Middle of Somewhere // Karli of Everyday Ellis // Paige of Hometown Heels 
Chelsea of Simply Pett // Megan of Being Mrs Fowler // Candice of Hello Pretties  



Jensyn of Stripes in Bloom // Heather of Heathered Hearts // Alexandra of Finding Alexandra 
Let me know what your favorite way to style the pencil skirt was in the comments below! Don’t forget to pin so you can save this article for those days you need ideas for dressing up your pencil skirt in a new way!

Pin It on Pinterest

Share This