8 Ways to Wear a Pencil Skirt With Boots
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  • Writer's pictureBrenda

8 Ways to Wear a Pencil Skirt With Boots

Updated: Sep 3

I think we can all agree that pencil skirts are a universal wardrobe staple. They are extremely versatile and can be worn from day (to the office) to night (hello Happy hour). A black pencil skirt is definitely the most popular of all pencil skirts and for good reason: black is a neutral color that is very easy to pair with other colors and it is also slimming.

A traditional pencil skirt is midi in length and is most often paired with a blouse, crop top or sweater.

I have an entire post dedicated to wearing a black pencil skirt and I invite you to check it out for even more inspiration for pencil skirt outfits. What’s great about pencil skirts is how easy it is to wear them across seasons. During the cooler months, midi skirts are a great way to stay warm yet stylish, depending on how you style them.

On today’s blog post, I would be sharing some of favorite ways to style a pencil skirt with boots so keep reading if you’re seeking some style tips to step up your classic pencil skirt look.


Whether your pencil skirt is a maxi skirt or midi pencil skirt, there are a pair of boots out there to go with it. My main style tip when it comes to pairing boots with pencil skirts is: the shorter the skirt, the taller boots get to be.

Ankle boots work best with maxi skirts while tall boots work best with shorter skirts. I hope that from this post, you would be able to see how easy it is to style a pencil skirt with boots. First, I would like to share some of my favorite places to shop for pencil 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.

i) Etsy is a great place to find handmade pencil skirts. You can find both a classic pencil skirt as a well as more flamboyant ones. This black pencil skirt comes in a pin-up style and could be paired with a pair of ballet flats or boots when it’s cold outside.

If your body shape is hour glass or pear-shaped, a customized pencil skirt may be the best option for you to ensure the perfect fit.

ii) Banana Republic is known for their polished office wear as well as business or business casual pieces. They make it easy to wear a pencil skirt in the winter with this wool pencil skirt, available in black and brown.

The wool would provide some extra warmth in the cold weather and you could easily pair this skirt with a sweater and knee-high boots. The best part? It comes with pockets!

iii) If you are looking for a pencil skirt to flatter your waist and accentuate your curves, high waist pencil skirts are your best friends. This one from Shein is the most affordable skirt on this list but has hundreds of great reviews.

It could serve as a great base for a casual pencil skirt outfit or be paired with a bustier for a sexy date night look. You may want to check out my post: the best ways to wear high-waisted skirts for some additional inspiration.

iv) Another great option for pencil skirts from Shein is this grey maxi one (other colors available). It would be so easy to pair with other colors thanks to its neutral color and the length would make it appropriate for various occasions.

One annoying thing about a long pencil skirt is how it can sometimes ride up when you walk. They are best paired with ankle boots or a pair of sneakers when opting for a more casual look during the summer.

v) Denim skirts are a fun way to rock the pencil skirt trend and Pretty Little Thing has this great stretchy denim version that would look great with flat shoes or heels. You could also easily mix it with different prints and colors thanks to the neutrality of the dark wash denim. If you prefer an even longer denim pencil skirt, check out this one HERE.

Now that I’ve shared my favorite sites to shop for midi skirts (and some great individual options), we are ready to proceed. Pairing pencil skirts with boots of different heights is what we are about to tackle so let’s dive right into it.

1) Long pencil skirt with ankle boots

Long pencil skirts tend to work best with ankle boots because they avoid bunching at the calves, keeping things nice and sleek. This corduroy skirt from Eileen Fisher is a great option to pair with either heeled or flat ankle boots. You could style it with a tucked in sweater and a trench coat for a chic Fall or winter look.

Get the look HERE

2) Knee-length pencil skirt with mid-calf boots

If you’ve been blessed with calves that are on the regular side or smaller, then high boots and pencil skirts are your best friends. You could show off a little skin by pairing a knee-high skirt with a pair of calf boots, leaving a little bit of leg on display.

If it’s too cold to show some skin, feel free to add a pair of opaque tights to your look. A turtleneck sweater in a solid color, as seen on the model, would be a great choice. During the warmer months, you could replace the sweater with a white blouse for a chic office look.

Get the look HERE

3) A plaid pencil skirt with knee-high boots

It seems like every time temperatures begin to drop, plaid pokes its head around the corner, just asking to be worn. I love how brands have recognized the world’s love for plaid and have found ways to incorporate it into different clothing items. This plaid skirt is a great example of how plaid can be worn at the office in a more professional manner.

A great way to style it would be with a top or sweater in a color featured on the skirt to really compliment it. Knee-high boots would hit just where the skirt ends and you could add a longline coat for extra warmth.

Get the look HERE

4) Leather pencil skirt with ankle boots

If it’s not too cold outside or you’re looking to create a sexy party look during the colder months, I recommend you pair a crop top or cropped sweater with a leather skirt (or faux leather skirt) and a pair of ankle boots. Combat boots could be worn for a more casual look and a leather jacket thrown on top of your shoulders for some extra warmth.

If you have short legs, try to stick to boots that are lower when pairing them with a shorter pencil skirt. Higher boots tend to cut you off at your calves or high ankle, making you appear even shorter.

Get the look HERE

5) Denim pencil skirt with boots

The perfect way to make a casual outfit from a pencil skirt and boots combination is by opting for a denim skirt. If your denim skirt is knee-level or higher, I recommend going with a pair of over-the-knee boots or knee-high ones. If your denim pencil skirt is below your knee, I suggest you go with a pair of boots that reach your mid calf or ankle boots.

It’s easy to make your legs appear longer in short skirts by adding a pair of heels. This time, add a pair of heeled boots. If you’re feeling extra Southern, this is a great opportunity to pair your pencil skirt with cowboy boots.

Get the look HERE

6) Pencil skirt with white boots

White boots are quickly picking up in popularity and can be seen paired with skirts of different lengths across different seasons. I have found myself loving this trend, so much so that I have an entire blog post dedicated to showing how to wear white boots.

Pencil skirts of any color work well with white boots thanks to their neutrality and subtle ability to brighten an outfit. You can create a sexy yet cute Fall look by pairing a straight skirt with a cropped top or tank top, a leather jacket and a pair of white booties. White ankle boots would go better with a maxi pencil skirt.

Get the look HERE

7) Slit front pencil skirt with boots

During the winter months, your pencil skirts with slits can still make it to your wardrobe. Consider pairing them with a pair of black tights or leggings, knee-high or over the knee leather boots and a top or sweater.

To make your skirt outfit more fun, try picking tops or sweaters in bold patterns such as zebra or leopard print. To create a more dressy outfit, opt for a formal shirt or a peplum top and tuck it in for a sleeker look.

Get the look HERE

8) Mini pencil skirt with knee boots

You can create a stylish look with a mini pencil skirt by styling it with the right style of boots. If you are wearing your skirt during the day, I suggest choosing a pair of knee or over-the-knee- boots. They could be flat boots if you want a more comfortable look or heels if you’re on the shorter side and wish to appear taller.

You could create chic monochromatic looks with your line skirts by matching your mini skirts to your sweaters. Complete your look with a long coat in a neutral color.

Get the look HERE

I hope that you have really gotten inspired when it comes to styling a pencil skirt with boots for different occasions. Remember that you don’t have to wait until the winter for some of these looks as crop tops and tank tops could be worn instead of sweaters.

The most important thing to remember is that regardless of your body type, there is a pencil skirt with your name on it. It would be wise to invest in a couple of pencil skirts that you can carry into the various seasons.

You should also check out my post on the best ways to wear a black skirt if you really love your black pencil skirts.

To see how to pair your pencil skirt with other shoes, check out my post: The top 8 shoes to wear with your favorite pencil skirt.

If you have an upcoming first date at a coffee shop, checkout my post: What to wear on a coffee date.

For those of you needing some shoe inspiration for your pencil skirts, check out my post: 13 Shoes to Wear With a Pencil Skirt Throughout The Year.

Not sure what to wear today? Check out my post: What to wear today.

For those of you looking to style a pair of cowboy boots, with your skirts, check out my post: 11 Styles of Skirts to Wear with Cowboy Boots.

Until the next post,



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