5 Ways to Wear a Pencil Skirt in the Winter
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  • Writer's pictureBrenda

5 Ways to Wear a Pencil Skirt in the Winter

Updated: Feb 13

We have already established on this blog that a black pencil skirt is a wardrobe staple. I love how versatile this style of skirt is and there is no reason why they cannot be styled for the winter. I have already shared several ways to style one on my post titled 15 ideas on how to wear a black pencil skirt.

You may want to check it out if you’re looking for some inspiration for pencil skirt outfits in general. On this post, I would be covering how to style a pencil skirt in the winter months specifically so keep reading if that’s what you came for.


When it comes to styling pencil skirts for the cold weather, it’s a matter of layering the right way and avoiding bulking. Regardless of your body type, you would be able to style a pencil skirt to suit your personal style. All you need is a pencil skirt that fits you perfectly.

If you’re on the shorter side, try to ensure the hem of your skirt does not go past your calves or else it would make you appear even shorter. Most pencil skirts are either knee or midi length, making them an office wardrobe favorite. They can also be style for casual or formal events with the right accessories.

As creating the perfect pencil skirt outfit starts with the perfect pencil skirt, I would like to share my favorite pencil skirts currently on the market. I have taken my time to ensure that these skirts come with good reviews so you can be at ease placing an online order. Just ensure you check to see if you need to size up or down with each option.

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

Where can I get a pencil skirt?

- Kit and Aces’ Serenity Pencil Skirt is a fitted pencil skirt in a stretchy double-knit fabric. This means it will flatter your curves while keeping you warm and being appropriate office wear. Could you ask for anything more? I love that it comes in various colors, allowing you to spice up your winter wardrobe.

You should try the dark plum color if you’re feeling a little cheery. This would be a great option to wear during the colder months with a white top and a pair of boots.

- Banana Republic’s Siena Wool Pencil Skirt is the perfect straight skirt to sport when it’s cold outside but you still want to look chic at a semi formal event. The wool fabric would keep you nice and warm while the classic cut of the skirt would keep things classy.

I especially love the came color option because it lends a slight pop of color while keeping things pretty neutral. You could style with pumps, just like the model or knee-high boots.

- If you’re looking for a very affordable pencil skirt with a unique look, this midi skirt from Shein should do the trick. You could pair it with different tops and sweaters to achieve different types of looks.

For example, you could pair it with a crop top for a casual event or a long sleeved sweater for a business casual look. The paper bag waist and self belt would also flatter your waist. It’s a win-win.

- For those of you looking for a great leather pencil skirt, Lulus has this great vegan leather pencil skirt at a great price. It’s a knee-length pencil skirt that comes in 3 classic Fall colors and in a classic straight cut. It could easily be paired with a blouse, cardigan or sweater on any given day.

Add a trench coat as outerwear for the perfect look. To emphasize your body shape, opt for a fitted bodysuit and you’re ready for a night out or date night.

- If you’re not one to shy away from bright colors, this Court & Rowe front slit pencil skirt in red is a great way to stand out in your pencil skirt in the winter. You could easily pair it with neutral colors such as white or black to create a great look that goes from day to night. Who says you can’t make a style statement when it’s cold outside?

- If you’re looking for a pencil skirt to turn heads during the holiday season, look no further than this long skirt from ASOS. I love the sequined detailing as well as the fringe which makes for quite the fun and head-turning look.

Pair it with high heels or heeled ankle boots for a chic look. You would want to reserve this skirt for special occasions as it’s a bit over the top for the office…unless your office is the Vogue headquarters.

Now that you have the list of my favorite pencil skirts out right now, let’s dive into the different ways to style your favorite pencil skirts during the winter. These are looks that should suit different body shapes and sizes as long as you’re working with a great pencil skirt.

Don’t be shy to remix them in ways that work better for you and for the event/location you’re headed to. You most likely already own most of the pieces mentioned below and so this may just serve as a guide you bookmark the next time you need some pencil skirt style inspiration.

How do I style a pencil skirt in the winter?

1) With an oversized sweater

A favorite way to style a pencil skirt for the cold weather is by wearing an oversized sweater on top. You could wear a tank top underneath for some extra warmth. You could also add a skinny belt in a bright color for a pop of color and to also accentuate your waist. It’s easy to create a chic monochromatic look by picking a sweater in the same color as your pencil skirt.

Get the look HERE

Complete your warm look with a pair of ankle boots. Heeled ankle boots in neutral colors are a good idea if you’re dressing for a slight formal occasion. For a fancy event, throw on a pair of nude heels. You can also partially tuck in your sweater for a more street wear vibe.

2) With a fitted sweater

During the cooler months, you can still show off your curves by pairing a fitted skirt with a fitted sweater. I love to mix and match colors of skirts and different tops to create different looks. If you’re not shy about your body, try pairing a form-fitting leather skirt with a fitted v-neck sweater for a great date night look that would also keep you warm.

You could complete your look with either knee-high boots or stilettos, depending on how cold it is outside. Don’t forget to throw a long coat over your shoulders before heading out!

Get the look HERE

3) With a leather jacket

When it comes to sleek and sassy pencil skirt outfits for the cold weather, nothing compliments them like a black leather jacket. If you’re feeling particularly sassy, go for a shorter pencil skirt and pair it with cropped sweater. Add a pair of tights for an extra layer of warmth and you could wrap a cute cowl scarf around your neck as well for the cold. I have a post on how to wear a cowl scarf which would be a great read as well.

Image source here

Combat boots would be the perfect choice of footwear to go with, but flat ankle boots work just fine as well. If it’s not too cold outside, replace your sweater with a graphic tee for a cute look you could wear for bowling with your friends.

4) With a denim jacket

A good idea for a casual pencil skirt outfit is a to pair your skirt with a simple t-shirt and add a denim jacket on top. If it’s particularly cold, replace the tee with a light sweater and add a pair of leggings or black tights. Feeling Canadian, you could go for a winter Canadian tuxedo look by pairing a denim pencil skirt with your denim jacket and breaking it up with an interesting top.

Image source here

Opt for denim skirts whenever the dress code is casual or if it’s Casual Friday at the office. If you want something warmer than a denim jacket but still want to stay with the denim on denim theme, you could go with a denim shirt and then add a jacket on top to stay warm. Cowboy boots are a welcome footwear option with this look.

5) With tall boots

When it comes to creating the perfect look with pencil skirts, a pair of tall boots can go a long way. If your skirt is knee length or shorter, you can show off your tall boots with ease. Pair a crisp white shirt with a knee-length pencil skirt, sheer tights and knee-high boots. This is a great corporate look if you have a boardroom meeting or presentation during the winter.

Image source here

You could either drape a cardigan over your shoulders as seen HERE or throw on a trench coat to complete this look. If you’re headed for a fancy occasion, add a statement necklace and perhaps a pair of pumps to elevate your look. If your pencil skirt is a mini one, you could rock a pair of thigh-high boots with a cute sweater for a more casual look.

I hope from this post you have gotten ideas for not just black pencil skirt outfits but pencil skirts in general. Feel free to play around with different colors of skirts and tops to create multiple looks. You can also play around with bold prints such as leopard print to add some character to your cold weather looks.

A pencil skirt is such a key wardrobe piece that deserves to be worn across different seasons. To stay extra warm, wear layers underneath your skirt such as leggings and layers underneath your sweaters and blouses, such as tank tops. If your pencil skirt is a maxi skirt, then your best choices of footwear would be ankle boots or heels (for special occasions).

If you enjoyed this post, you may want to check out my post on how to wear maxi dresses in the Fall and winter.

I also have a post on how to wear flat booties with anything. It’s a great guide to styling ankle boots no matter the season.

For inspiration on how to wear a denim skirt, check out THIS POST here.

Until the next post,



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