Skip to Content

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

“Why are women obsessed with shoes?” written after “What shoes to wear with pencil skirts?” describes pretty much everything we search for on Google when we’re running out of outfits to wear. Worry not, you’re not the only one who spends her Friday nights pining after those sheer, black-ribbon Jimmy Choos.

And, we can’t even blame ourselves for wanting to update our shoe collection every three to four business days when we remember how much better (and more productive) we are the moment we wear high heels.

Sure, our feet hate the feeling of carrying the world’s weight. But, we adore the feeling of towering over everyone. Of course, the whole thing started with Cinderella and her glass slippers.

When we grew a little older, we fell head over heels for Carrie Bradshaw and her Manolo Blahniks. And, when we heard Cardi B rapping about her red bottoms we learned how much money we need to save for Christian Louboutins.

Whether you’re looking for the perfect shoe that’s bound to make you transform from the lady that works at the library to Rosie Huntington-Whiteley going about her day.

Whether you’re looking for a comfortable shoe to wear with your pencil skirt without resembling someone’s grandma (or even worse, a millennial?!). We’ve got your back, girlie!

We’re bringing you fifteen pairs of shoes to wear with a pencil skirt depending on the weather, the occasion, and the style you’re going for. Buckle up because we’re about to blow your mind with how easily the right pair of shoes can make your outfit pop… Or flop.

I’m out of ideas: what shoes to wear with a pencil skirt?

1. Stilettos

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

Stillettos are a great way to wow everyone at work and get a free foot massage from your significant other at the end of the day.

Stilettos aren’t the right choice for anyone who’s looking to wear something comfortable with a pencil skirt because these shoes are literally determined by the height, the width, and even the shape of the heel.

But, stilettos and pencil skirts are a match made in heaven. So, when looking for an elegant shoe to wear with your favorite pencil skirt (preferably a leather one), you can’t go wrong with stiletto sandals, stiletto pumps, or even stiletto peep-toe pumps.

Whether you’re ballin’ on a budget or eager to splurge on Louboutins, don’t be surprised when you start turning heads wherever you go.

2. Pumps

DREAM PAIRS Women's Annee Black Nubuck Low Heel Pump Shoes - 9 M US
$45.99 $32.28
Buy Now
We earn a commission if you make a purchase, at no additional cost to you.
03/17/2024 02:55 am GMT

Pumps have to be one of the most popular shoes out there, and that’s why you shouldn’t be surprised to see them as one of your safest bets when you’re looking for a shoe to wear with a pencil skirt.

Pumps, also known as court shoes, go with pretty much every outfit you can think of. From formal events to casual brunches, pumps can save the day!

We know what you’re thinking, though. “There are too many styles of pumps to choose from. How do I know which ones go with a pencil skirt?”

Right off the bat, classic pumps are lightweight, elegant, and chic whether you combine them with a leather skirt for a night out or a suede skirt and a sweater for work.

On the other hand, Mary Jane pumps can add a dash of je ne sais quoi to whatever you’re wearing (not to mention the strap that makes them super comfortable). Of course, we can’t forget about slingback pumps which seem to be a recurring theme on runways these days.

3. Strappy sandals

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

When we’re talking about the summer footwear department, we’re focusing on strappy sandals for a reason.

Timeless and versatile, strappy sandals have taken the fashion world by storm. We’re not about to argue with designers such as Daniel Lee at Bottega Veneta, Gianvito Rossi, and Hedi Slimane.

First off, strappy sandals are a great shoe to wear with a pencil skirt when you’re looking to transform your outfit from office wear to something more appropriate for brunch with your girlfriends.

Swap the stiletto pumps for strappy sandals and the structured white blouse for a white T-shirt and you’re good to go.

Oh, there’s hardly a shoe that screams “I’m fashionable!”  more than a strappy sandal combined with pretty much anything you already own.

Even the fashionable babes on Instagram such as Rosie Huntington-Whiteley and Blake Lively use strappy sandals to accent everything from polished attire to rolled-out-of-bed outfits.

4. Mules

Maypie Womens Flat Mules Closed Pointed Toe Slip On Loafer Slides Backless Shoes, Black, 5 B(M) US
Buy Now
We earn a commission if you make a purchase, at no additional cost to you.
03/17/2024 02:50 am GMT

We love to hate on mules, but we must agree that they’re one of the most fashion-forward shoes you can wear with a pencil skirt.

On the one hand, pencil skirts are a great way to achieve that effortless, polished look. On the other, they’re often seen as a safe (and a boring) option when you’re running out of outfits.

Therefore, when you’re looking for a shoe that’s going to spice things up, you’re on the right track to succumb to the allure of the mule shoe.

Mules, on the off chance that you’ve been living under a rock, are a style of shoe that doesn’t have a back or support around the foot.

They can be completely flat or have a kitten heel, a block heel, or a stiletto heel. Other than that, mules can have open toes, straps, or other embellishments that make them stand out.

And, mules can make you look like you came straight from the cover of Vogue magazine when you opt for the Manolo Blahnik ones (and have your own Carrie Bradshaw moment!).

5. Open-toe mules

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

Oh, you want to make mules more attractive? While stiletto mules reign supreme when we’re talking about styling shoes with a pencil skirt, open-toe mules can work wonders with a more relaxed, spontaneous outfit.

Now, you can combine a nude open-toe mule with a nude bodysuit (Skims might be a great option) and a denim pencil skirt for a summer outfit worthy of an Instagram post.

On the other hand, you can combine a dark-colored, open-toe mule with a white, ankle-length pencil skirt and an oversized blazer for a trendy look.

We’re focusing on heeled mules because they’re more appropriate for an office or a workplace that requires you to wear a pencil skirt.

Flat mules can be a basic, neutral starting point for an outfit, but they can look bottom-heavy when combined with a pencil skirt. Opt for heeled mules for added height (and a boost of confidence!).

6. Clear shoes

Clear shoes are the ultimate nude shoe you can wear when you’re trying to make your legs look longer.

Even though the clear clothes trend earned a reputation for not being the most comfortable or wearable, clear shoes have been making a comeback on the runway for the past couple of months.

Kim Kardashian brought the trend back when she wore the famous Yeezy heels back in 2016 (now, that didn’t age well).

And, she’s often credited as the trendsetter that’s been keeping the clear shoe movement alive and kicking for many, many years.

Whether you’re a fan of the Kardashians or not, there’s nothing stopping you from wearing clear shoes combined with a pencil skirt to an occasion of choice.

Clear shoes are bound to draw attention to everything you’re wearing above them – don’t shy away from going crazy with your pencil skirt patterns, fabrics, and textures.

7. Wedges

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

Wedges are a great alternative for any of your girlies that aren’t thrilled about wearing stilettoes and high heels.

They’re guaranteed to give you a boost of confidence and attitude without hurting your feet as much. They are also perfect for backyard barbecues, weekend weddings, and summer pool parties.

Wedges are a comeback style of shoe that has stood the test of time. They can be dressed up or dressed down, depending on what you’re planning on wearing with your pencil skirt.

Raffia woven wedge shoes, for example, can work great with a shorter skirt and an oversized white button-up (with rolled-up sleeves, of course).

Transparent wedges, such as Simon Miller Ghost wedge sandals, can bring some structure to a regular black pencil skirt.

Whether you love them or hate them, they’re a staple when we’re talking about celebrity street style, too. Jennifer Lopez, Reese Witherspoon, and Meghan Markle adore the comfort and style that wedge shoe brings to the table – and, they wear them all the time.

8. Block-heel shoes

Steve Madden Women’s Charlize Pump, Black Satin, 10
$139.00 $97.90
Buy Now
We earn a commission if you make a purchase, at no additional cost to you.
03/17/2024 11:43 pm GMT

Here’s another one for anyone who doesn’t appreciate the concept of suffering for the sake of beauty. Turns out you don’t have to spend the entire event screaming (silently, of course) because your stilettos are digging through your feet.

Block heel shoes and/or platform shoes are a style of shoe that’s characterized by large, square heels and chunky soles that make walking in them a breeze.

When you’re looking for something to combine with a leather pencil skirt or a skirt made from a similar thick fabric, wear block heels and you won’t go unnoticed.

Even huge fashion houses such as Prada, Balenciaga, and Versace use block, platform heels to play on the “ugly shoe trend” and show how easily you can elevate an outfit with a simple addition of the right shoe. And if you don’t want to splurge on heels, then Steve Madden has a great knockoff for a fraction of the price.

Zendaya, Lady Gaga, and Hailey Beiber seemed to have gotten the memo because you won’t catch them wearing other shoes.

9. Chunky loafers

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

While we’re on the topic of Hailey Beiber… She absolutely adores the trend of wearing chunky loafers with pretty much anything.

Loafers are a timeless addition to your wardrobe and you should purchase them before you start wondering which shoes to wear with a pencil skirt.

While they do stand out when you combine them with tailored trousers or dresses, they’re even more eye-catching when worn with tights, knit socks, and the ever-elegant pencil skirts.

And, to make things even better, you can get them anywhere (for any price range) because they’ve become a staple of the season.

From Gucci horsebit-detailed, metallic, embroidered, leather platform loafers you can get for a staggering price of $1,150 to the Zara lug sole loafer you don’t have to count more than $60 for, you’re free to take your pick.

10. Sandals

The Drop Women's Samantha Flat Strappy Lace-Up Sandal, Doe Tan, 7.5
Buy Now
We earn a commission if you make a purchase, at no additional cost to you.
03/17/2024 02:29 am GMT

When you’re wondering what shoes to wear with a pencil skirt, don’t overlook the power of a flat, strappy sandal.

While we don’t necessarily think of flats when we’re trying to think of something that goes with a pencil skirt, there’s a chance we’re missing out because we’re closed-minded.

Sandals can electrify your summer look even when you’re wearing something as “boring” as a pencil skirt. No matter what your style preference might be, strappy sandals can help you keep things more contemporary and modern without compromising comfort.

And, strappy sandals have been all the rage on the runway lately which means you would be reaching fashion’s highest requirements with your picks.

Choose between nude strappy sandals to elongate your legs, silver or gold sandals to make a statement, or regular dark (a.k.a black sandals) to keep things on the safe side.

11. Slides

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

Whether you’re a minimalist or a maximalist at heart, you’ve probably seen every celebrity out there sporting those beautiful brown Hermès slides.

And, you’ve noticed they’re winning the fashion game with satin skirts and white T-shirts (not to mention the raffia woven handbags).

Slides are the safest way you can style a pencil skirt without looking like you don’t know where you’re going. Sure, stilettos and pumps elevate the look and make you feel like a million dollars.

But, slides make you look like you haven’t even tried and you still managed to look as fashionable as ever.

Remember that Keeping up with the Kardashians line “I have seven stylists who put me in sweats and leggings. I just like that effortless look but, you know, it’s really a lot of effort?”

Now, that’s what we’re talking about when we’re suggesting you wear a pencil skirt with slides.

12. Ankle boots

MIA Women's Carla White 8 M
$69.99 $16.79
Buy Now
We earn a commission if you make a purchase, at no additional cost to you.
03/17/2024 02:34 am GMT

Who doesn’t love a good ankle boot like these MIA ones? Paired with a pencil skirt moment? We know we do, and we’re happy to offer you some suggestions on how you can style these two wardrobe essentials together.

First off, make sure you choose the right material. Combining thicker materials (chunky sweaters) with thinner ones (silky, flowy skirts) always works.

But, when you’re looking to combine something with your leather or tweed pencil skirt, you might want to go for a thinner, cashmere turtleneck.

Add some ankle boots that are the same color as the rest of your outfit and voilà – you’re the monochromatic goddess of styling you always wanted to be.

13. Chunky boots

What Shoes To Wear With A Pencil Skirt? 15 Style Suggestions

We can’t seem to escape the chunky trend. And, to be completely honest, we don’t want to! When you’re looking for shoes to wear with a pencil skirt without looking too preppy or too elegant, you should go for chunky boots.

Chunky shoes have been popular for the past couple of years, and they definitely continued being one of the most worn styles by celebrities and influencers alike.

Whether you’re looking to expand your horizons with something you haven’t worn before or you’re looking forward to learning how to style these two (very different) pieces, you came to the right place. 

A statement sweatshirt with a white button-up peeking through, a body-hugging pencil skirt, and a pair of chunky boots should do the trick. Play with the color scheme that works best for your style and you should be happy with the results.

14. Knee-high boots

Can we all agree there’s hardly anything better than a combination of knee-high boots and a structured, fitted pencil skirt?

Whether you’re going to an office party or meeting some friends for lunch, knee-high boots can make you look like you spent hours looking for the perfect outfit.

Now, black boots go with pretty much everything and we suggest you don’t go through the season without purchasing a pair you really, really like.

Black knee-high boots are the ones you’re always going to come back to whether you style them with jeans, a dress, or a pencil skirt.

Brown boots are great when you’re a fan of the cottage core aesthetic or appreciate the nude fashion trends that have been everywhere lately.

Combine them with knitted, champagne-colored skirts and chunky sweaters. Add a suede belt with gold accents and you’re done.

15. Sneakers

Veja Women's Esplar Logo Sneakers, Extra White/Black, 4 Medium US
Buy Now
We earn a commission if you make a purchase, at no additional cost to you.
03/17/2024 02:40 am GMT

We saved the best for last and we hope you agree! While some of you might think that the trend of combining sneakers with dresses and tailored trousers doesn’t deserve our time of the day, we beg to differ.

We’re delighted by the fact that we can finally wear something comfortable to the office without being targeted by the fashion police.

Whether you’re wondering what shoes to wear with a pencil skirt because you’re bored of whatever you’ve been wearing recently. Whether you’re searching for suggestions because you haven’t thought of styling pencil skirts with anything other than stilettos and pumps. 

Combine your favorite sneakers with a pencil skirt that’s been collecting dust in your closet, and you’re ready to run errands looking like Rosie Huntington-Whiteley!

If you’re on the hunt for a new pair of sneakers, then these Veja Women’s Esplar Logo sneakers are definitely a great option. They’re sophisticated and classy and will pair great with every outfit you can think of. So, you can wear them with more than just a pencil skirt.

What Shoes To Wear With A Pencil Skirt 15 Style Suggestions