The Top 8 Shoes to Wear With Your Favorite Pencil Skirt
top of page
  • Writer's pictureBrenda

The Top 8 Shoes to Wear With Your Favorite Pencil Skirt

Updated: Jun 9

As mentioned previously on this blog, A pencil skirt is a staple piece that needs to be in every woman's closet. No matter your age, body type or personal style, there is a way you can rock one. A pencil skirt could be paired with any top from a crop top to a blouse or s even a graphic tee.

A black pencil skirt is such a versatile piece of clothing that can be dressed up or down for different occasions. Whether you are including one to your office wear or heading to happy hour, they can be the core of many stylish outfits. You could easily pair one with the tops and sweaters already sitting around in your closet.


It seems a large portion of all pencil skirts tend to be midi skirts, making them give off a more professional look. This is what makes them common at the workplace and a great option to wear to a business meeting. You can also dress them down to create more casual looks

In today’s blog post, I would be going over the best shoes to pair with your pencil skirts to create stylish outfits. You’ll see for yourself just how easy it can be to create a chic pencil skirt outfit If you have the right shoes. I already have a post titled: 5 ways to wear a pencil skirt in the winter which covers how to style your pencil skirts during the colder months.

You should consult it if you’re planning on stepping out in a pencil skirt during the winter. This just goes to show you that you don’t have to pack your pencil skirts away once the cold weather hits.

Get the look HERE

For today however, we would be going over the different shoe options to choose across different seasons. You may discover a new way to style your knee-length pencil skirt from this post. Your next stylish look is just a pencil skirt away so keep reading if you’re interested in putting your best foot forward this year. Feel free to bookmark this post for future reference.

Before we hop into the various types of shoes to pair with your skirt, I would start off by sharing some of my favorite pencil skirts and where to find them. As a curvy woman, I know how hard it can be to find a pencil skirt that fits just right. I have gathered years of experience and can now share some of my favorite sites to shop for pencil skirts as well as other styles of skirts.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

Where to shop for a pencil skirt

i) Lulus

Lulus offers a decent range of pencil skirts for the trendy woman. I particularly love their vegan leather pencil skirts which come in beautiful rich solid colors. If you’re looking for a midi pencil skirt to turn heads in however, you may want to check out THIS black pencil skirt with a slit. You could pair it with a white blouse or with a crop top for a more casual look.

ii) Nordstrom

If you are looking for a pencil skirt to wear during the cold months, then THIS Eileen Fisher skirt is a great choice. It’s professional enough to wear to the office and you could also pair it with a nice blouse or sweater to wear to church or to a winter wedding. Throw on a pair of ankle boots to complete your stylish winter look.

iii) Amazon

If mini skirts are your thing, then by all means, show off those legs. During the warmer months, try opting for shorter pencil skirts to create simple sexy outfits. You could pair your mini pencil skirt with a crop top, t-shirt or tank top for a simple yet sexy casual outfit. Feel free to add a pair of flat sandals or sneakers to maintain the casual feel of your entire look. For date night, slip on a pair of heels.

iv) Shein

Shein probably offers the most options for pencil skirts on this list. You can find a pencil skirt for every occasion and of every length on the website. Regardless of your body shape, there is something for you.

Denim skirts are a great way to create chic casual outfits during the summer if you’re on vacation. A denim pencil skirt such as THIS ONE could easily be paired with sandals, sneakers or a pair of high heels to create a stylish outfit.

v) Good American

The Good American brand has been getting pretty positive reviews, especially for their skirts and dresses. A black leather pencil skirt is a sexy staple you can wear year-round. Pair it with strappy heels for a night out or with a pair of flats for a trip the museum. THIS black leather skirt comes with a high back slit which allow for more movement while adding a touch of sex to your outfit.

Now that you have a good idea of where to shop for different styles of pencil skirts, let’s talk about the perfect shoes to go with them. Your shoe style would depend on the dress code of the event or place you are headed to as well as the weather. I would try to cover as many different options as possible to cover each of these scenarios.

What shoes to pair with a pencil skirt

1) Ankle boots

Pairing your pencil skirt with boots is the perfect way to style them during the cooler months. Ankle boots work best with a long pencil skirt so that they don’t get hidden by your skirt. You could wear a chunky oversized sweater if it’s a cold day or a more form-fitting sweater for a cute Fall look.

Get the look HERE

Choose a pair of flat ankle boots if you’re going to be doing lots of walking or if you’re not particularly comfortable with heels. For a casual outing, opt for a pair of combat boots. Chelsea boots are your best option of ankle boot if you’re going for a business casual look. Start with a pair of boots in a neutral color if you’re just starting to build your wardrobe.

Do check out my post: 8 ways to wear a pencil skirt with boots for some more style inspiration for pairing pencil skirts with boots.

2) Stiletto heels

Stiletto heels should be your shoes of choice if you’re looking to create a sexy yet elegant look with your pencil skirt. If you have short legs, make sure you go for pencil skirts that are knee length or above to look taller. A pair of strappy heels would also make your legs look longer if they have a thin ankle strap or none at all.

Get the look HERE

If you are headed for a special occasion such as a birthday or wedding, style your pencil skirt with a fancy blouse or top for a chic look. Tuck your blouse into your skirt to make your waist appear even smaller. If outerwear is necessary, I recommend a trench coat or a different longline coat.

3) Flats

Flat shoes don’t get enough love on the blogs. For some reason, when we speak of stylish outfits, we tend to omit flats. A pair of ballet flats are a good match for your pencil skirt outfits to the office, for weekend gatherings and also for formal events. To make your outfit more formal, opt for sleek flats such as patent leather ones.

Get the look HERE

If you are dressing up for formal occasions, you could even choose a pair of flats with some bling on them. This would help elevate your entire look even further. A short pencil skirt paired with flats and simple top makes for an easy casual wear outfit you could wear to the mall.

4) Knee-high boots

Tall boots are a great choice to go with your shorter pencil skirts. This is because your skirt won’t hide the beauty of your boots, which should be on display. One of my favorite ways to style my knee length pencil skirts during the Fall is by pairing them with a cropped sweater and a black leather jacket. You could also opt for a tank top if the weather is warm enough.

Get the look HERE

A pencil skirt with a front slit could be styled up or down to create a stylish yet sexy look. Consider pairing it with a simple t-shirt for a casual look you could wear for coffee or pair it with a crop top and leather jacket for date night. A classic pencil skirt could also be paired with a simple blouse and knee high boots for a classic look.

5) A pair of sneakers

Pairing your pencil skirt with sneakers is an easy way to create a simple casual look. This works for your maxi skirt as well as midi and mini pencil skirts. My favorite sneakers to wear with any skirt or dress are white sneakers. A pair of white sneakers adds a freshness to any casual outfit.

Get the look HERE

You can pair your sneakers with a mini pencil skirt and a denim jacket for a cute look you could wear to class. If you own other sneakers in different colors, they can also be paired with your pencil skirts to create fresh laid back looks. Switch up your pencil skirt look by opting for a pair of sneakers instead of a pair of high heels.

6) Flat sandals

Going on vacation to the South of France or Eastern Europe? Pack a pair of flat sandals to pair with your pencil skirt. Pair your pencil skirt with tank tops, t-shirts and cropped tops for some simple chic vacation outfits. If you’re headed for a fancy dinner, try wearing an off-shoulder top to create an elegant look with your pencil skirt.

Get the look HERE

A white pencil skirt would look great on a hot summer day. Try pairing one with a peplum top and a pair of flat strappy sandals for a trendy outfit. Don’t forget to add your crossbody bag.

7) Pumps

A pair of classic pumps are the right type of shoes to pair with a midi pencil skirt. This is a popular outfit worn by powerful women in boardrooms across the globe. Complete your look with a long-sleeved blouse in a solid color if your office has a business dress code. You could add a structured blazer to complete this look for corporate settings.

Get the look HERE

If you’re dressing for a less professional event, feel free to pair your line skirt with a top featuring bold patterns. This would make your outfit more interesting. Instead of going for the usual black pumps, show your personal style by choosing pumps in a bright color. If high heels scare you, try a pair of pumps with kitten heels.

8) Mules

Mules are the perfect pair of shoes to pair with your pencil skirt if you’re headed for a semi formal function. A pair of clear heeled mules would make your legs look longer and could be worn to a cocktail event. I would recommend you go for heeled mules if you’re going for a dressier look. Keep the flat mules for more casual outings.

Get the look HERE

I hope this list has proven useful to you. The most important thing to remember is that your choice of shoes would depend on the dress code of where you’re headed. The right pair of shoes can go a long way in helping you create a stylish look and all of the ones mentioned in this post would do that.

Do check out my post: 15 ideas on how to wear a pencil skirt for more ideas for pencil skirt outfits.

My post: 7 Shoes to Wear With a Blush Dress offers some of the best shoes and shoe colors to pair with a blush dress.

Until the next post,



bottom of page