How To Wear A Pencil Skirt At Any Occasion

Jan-Michael Quammie Wearing Gucci Pencil Skirt
Credit: Jan-Michael Quammie Wearing Gucci Pencil Skirt, Brown Fashion

We love pieces of clothing that tick multiple boxes, such as: stylish, sophisticated, versatile, and multi-functional. This is why we are such fans of the humble pencil skirt. It’s been a long-term part of a more formal office wear wardrobe, but we know it can be so much more than this. That’s why we’ve put together this handy guide on how to wear this staple item for many more occasions. It’s time to learn about the ideal tailoring for your body, as well as what you can wear with your skirt, from tops to bomber jackets.

Read more women style guides and shop womenswear from all the best stores in one place on Nuji.

Why We Love Pencil Skirts?

We can thank the likes of Prada and Gucci for bringing these beauties back into the limelight. You only need to look at a collection of Prada pencil skirts to see why they should remain as a staple in our wardrobes. Gone are the basic corporate vibes, and instead they’ve been replaced by lots of different cuts, designs and colours. It’s no longer a situation where one skirt is made for all, as we’re now all catered to, regardless of our shape and size.

It’s for this reason that we’re so keen to share the pencil skirt love. More recent designs are made to be fitted, but not skin-tight, and have been made in a glorious range of materials such as knits and vinyls. That means that they can be worn for many more occasions than in the office, such as for evening events, and even relaxed day wear when worn with a pair of more casual shoes.

Off-White Pencil Skirt Worn By Model
Credit: Off-White Pencil Skirt Worn By Model, 24 Sèvres

We think that you’ll also be a pencil skirt convert when you read through the rest of this guide; you’ll quickly learn how chic you can look with minimal effort! First we’ll cover how to style your pencil skirt for different occasions, from day to night.

How to Style Your Pencil Skirt?

Before we take a look at workwear versus evening wear styling, let’s cover the a few points on the lengths of pencil skirts. Traditionally an office skirt would be tailored to knee height or lower, which is why a midi length is probably more suited for workwear. However, you may have seen a mini pencil skirt that has caught your eye. This could be the perfect item for an evening event instead, so don’t write off your purchase just yet.

For Workwear

Even though pencil skirts have been established as office-friendly attire for a long while, you don’t have to continue doing the same old thing with them. Ultimately you will want to look professional whilst at work, but that doesn’t mean you need to pick something that leaves you feeling flat and uninspired.

With the recent boost in interest in these skirts, you’ll find so many more styles than you would expect, even if you need to stick to a black, grey or relatively safe colour palette. For example, you could look for a tweed number to see you through autumn and winter, or something a bit lighter with a belt or button detailing for spring and summer.

If you do have a little bit more freedom with the colours and prints you could wear, you’ll find many midi length skirts in florals, tartans, and ginghams, just waiting to be discovered. We think that pale pinks, bold greens, and royal blue colours could very easily be worked into office attire, assuming you’re allowed something a bit brighter.

For an Evening Event

When it comes to after work time, you might dare to lose a few inches from the length of your pencil skirt. Of course, you can still rock a midi length skirt if you prefer, especially if you want something a bit more special such as one made from leather or covered in sequins. The choice is up to you though, and if you are looking for a mini rather than a midi, you’ll find a great selection to choose from.

Some of our favourite finds include those that are perfect for showing off; you’ll be ready for all the selfies if you choose something metallic, ruched or embroidered. The metallic pencil skirts can work really well with simple blouses and elegant jewellery, so they’re a good place to start if you’re not too sure what to buy first.

If you are able to wear something more akin to a mini pencil skirt to your place of work, you’ll find it incredibly convenient when it comes to getting changed for an evening event once you leave the office. It can sometimes just be a case of changing your shoes and accessories and you’ll be ready to go; this is what we mean by saying that a pencil skirt can be highly versatile.

You may also feel comfortable wearing your mini skirt to some other social occasions such as brunch with the girls, or a trip to get cocktails during the daylight hours on the weekend. It doesn’t just have to be for evening wear!

How to Find a Pencil Skirt?

Now you know what is better suited for wearing to the office, and what is more appropriate for those evenings when you’re out and about, it’s time to start learning more about your perfect pencil skirt in both shape and style.

To put it into perspective, think about jeans for a minute. You’ll love the way some cuts fit on you, but you’ll avoid others as they don’t hug you in the right places, or hug too tightly in others. This is exactly the same when it comes to pencil skirts, as they can be tailored to fit better on certain body shapes and sizes.

Tweed Checked Pencil Skirt Worn By Model
Credit: Vetements Tweed Checked Pencil Skirt Worn By Model, Matches

Use our simple tips to get an idea of which skirts you should be looking at as your favoured fit; it should make finding your perfect pencil skirt a much easier process.

For Hourglasses Figures

Hourglass figures are best described as curvy, with a well-defined waist.

If you have an hourglass figure, we think that the ideal pencil skirt for you is one that is high waisted. For daytime wear you will be able to rock your skirt with a shirt, just tuck it in with a small amount hanging over the top of the waistline. Depending on the time of day and function type, you may also find that a crop top can look stunning too; this might be more appropriate for heading out to a club or bar, rather than a gallery or sit-down meal.

For Pear Figures

You’re closest to a pear shape if your hips are the widest part of your body.

If you’re a pear, go for the closest you can get to an A-line skirt. As these styles highlight the smallest part of your waist and flare out over your hips, you can recreate this by wearing a high waisted pencil skirt and getting clever with what else you wear. Try wearing a slightly oversized top, sweater or blazer. It should come down to the hips, and you can play around with leaving it untucked, or tucking it in. Crop tops can also be a great tool for showing off your slimmest parts.

For H, O or V-shaped Figures

Other shapes such as the apple (or ‘O’), where you have a slim lower body and are biggest around your middle, and the ‘V’ where you’re broader up top, can also suit wearing pencil skirts.

We recommend a slightly oversized top with a low rise skirt. The top should come down to the hips, or even lower if you prefer. A low neck top can work well if you don’t want to be drowning in extra material, and creates a nice balance. Showing off a little bit of skin can give you that stylish and sexy look you might be after for an evening out.

For Figures with Short Torsos

If you have a short torso, you might prefer to wear a top that is untucked, or a longer crop top. In terms of the skirt you choose, find one that is low or mid rise for the most flattering fit.

What We Love to Wear with Pencil Skirts?

The next item on the agenda is to find out what other items of clothes go well with pencil skirts. This will help you to test out different looks in line with your body shape and size which we just covered in the section above.


There is a whole range of tops that can look beautiful with pencil skirts. For a more casual look, choose something like an oversized or tight fitted t-shirt, or a sweater, whether loose or more fitted. You can get the ‘night out’ vibe with a crop top or vest top, in a bodycon style or a looser fit. Smarter evening events, are the time to bring out your blouses and peplum tops, and they’re also good for the office too.


For the days you’re in the office, you may want to layer up with a blazer to keep slightly more covered up and warm. Social events away from the workplace are ideal for more casual jackets such as bombers and leather jackets. If your skirt is a simple colour or design, you can probably afford to pick a jacket that is a bit more bold, but keep it relatively plain if your skirt is the brightest part of your outfit.


The final part of your outfit will be your shoes, and there are good picks for both smart and casual looks. Pumps are great for casual and smart casual days, whereas heels with straps will be your go-to choice for smarter occasions. You can also experiment with ankle boots and flats, to see what you can come up with for lots of different events.

Quick Tips for Styling Pencil Skirts

  • Midi length pencil skirts are ideal for your office wardrobe as they are already recognised as workwear.
  • Mini length pencil skirts are more suited to eveningwear when you aren’t confined to the same dress code rules.
  • Hourglass figures and pear figures look great with high waisted pencil skirts; try pairing your skirt with a crop top if you’re pear shaped.
  • Apple shapes look great with a low rise skirt and a slightly oversized top.
  • Play around with different tops, such as t-shirts and sweaters for a casual look, and blouses and peplum tops for a smarter event.
  • Blazers pair well with pencil skirts for office wear; try leather and bomber jackets for a more casual look.
  • Try out pumps, flats, ankle boots and strappy heels for the finishing touches to your outfit.

On That Note

Now you’ll be able to go from day wear to evening wear with confidence; it’s all about those little extras that you choose to wear with your pencil skirt, as well as finding the right one to suit the shape and size of your body. Remember that you can find different skirts to wear throughout the year, so you’ll have something to put on whether it’s a chilly autumn morning or a warm spring evening. Have fun experimenting with your outfit, putting together your skirt with tops, jackets and shoes that result in fresh new looks every day.

Looking for more?

Women style guide »

Women style guide »

Our editors do the hard work for you so you get inspired daily for a better style and lifestyle.

Shop womenswear »

Shop womenswear »

Shop the latest womenswear from the best stores in one place and find an eclectic mix of pieces to discover on every visit.

Shop sales »

Shop sales »

Shop the best womenswear sale with up to 80% off from all the best online stores in one place.

to top