What Shoes Go With A Pencil Skirt?

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A pencil skirt is a closet staple for many of us. There is something about their stylish, versatile simplicity that always makes you look well put together.

Their longer length and sleek silhouette not only make them perfect for a fancy night out… but also office appropriate. There is something about a pencil skirt’s simplicity that also makes them great for casual wear as well.

Pencil skirts are versatile enough that they can be dressed up or down. The shoe you choose to pair with a pencil skirt are key to defining the look you want to create.

What shoes go with a pencil skirt? In this article, we’ll look at several fantastic footwear options that pair with pencil skirts. We’ll also give some tips on how to wear your pencil skirt to look amazing!


What Shoes Go With A Pencil Skirt?

Here are six of our favorite different styles of shoes to wear with a pencil skirt. We are going to take a look at more formal and dressy styles, and then move to the more casual looks.

Let’s get to it!

Photo by Apostolos Vamvouras on Unsplash

1. Block Heel with an Ankle Strap

A block heel with ankle strap is both sexy and super stylish. Pointy-toed, spiky stilettos can be a bit much sometimes, not to mention they are not the most comfortable shoes to wear. And then there’s the ever impending danger twisting an ankle.PLus the whole thing about not being able to walk on grass or getting stuck between pavers and in drainage grates. Stilettos may be ‘sexy’, but not really practical for the real world. 

A block heel provides both stability and comfort. They are also more chic and sophisticated, and can work even in an office setting. Both open and closed toe block heels look great with a pencil skirt and you can choose the height you are most comfortable with.

Credit: Instagram / frenkeldora
Block Heel 1 Block Heel 2 Block Heel 3

But just a note to those of you who have shorter legs… an ankle strap will tend to kind of cut you off at the ankles, making your legs appear shorter. For you all, our next option is a better choice.

Allegra K Women's Crisscross Ankle Strap Burgundy Block Heel Sandals - 5 M US
Allegra K Women's Crisscross Ankle Strap Burgundy Block Heel Sandals - 5 M US
Vamp: Faux Suede; Outsole: Rubber; Heel: ABS; Occasion: Party, Office, Casual, Halloween days, Christmas Days, Dating, Evening
$40.99
Herstyle Rosemmina Womens Open Toe Ankle Strap Chunky Block High Heel Dress Party Pump Sandals Black 7.0
Herstyle Rosemmina Womens Open Toe Ankle Strap Chunky Block High Heel Dress Party Pump Sandals Black 7.0
MEASUREMENTS: approx. Heel height 3.75". True to size Fit.; Ankle strap with adjustable buckle closure.
$37.99

2. Closed Toe Pumps

Closed-toe pumps are classic shoes that will never go out of style. They can be cute, casual, dressy or formal, and always feminine. You can choose the height you feel the most comfortable in. 

As we mentioned above that an ankle strap will tend to make short legs appear shorter. A classic pump on the other hand, will do just the opposite!

Opt for a bit of a heel to make your legs look even longer!

Credit: Instagram / leiaslittlelooks
Pump 1 Pump 2 Pump 3
DREAM PAIRS Women's Mila Royal Blue Low Chunky Heel Pump Shoes Size 5 M US
DREAM PAIRS Women's Mila Royal Blue Low Chunky Heel Pump Shoes Size 5 M US
Classic Round toe & Trendy Colors; Heel height: 1.5" (approx); Platform height: 0.25" (approx)
$29.99
NINE WEST Women's Flax Pointed Toe Dress Pump, Red Patent, 11
NINE WEST Women's Flax Pointed Toe Dress Pump, Red Patent, 11
Pointed-toe pumps.; Available in a variety of different uppers including synthetic and leather materials.

3. Mules

Mules are not only super easy to wear, but also super versatile and can be worn with a variety of outfits – including pencil skirts. Their backless design makes them easy to slip in and out of and gives your feet a little room to breathe, while still looking fashion forward. 

Mules come in all sorts of styles, from flats and wedges to platform and heels, all of which look great with a pencil skirt.

Credit: Instagram / vsztaba
Mule 1 Mule 2 Mule 3

4. Flats

The perfect casual look is one that looks effortless… like you just threw clothes on and yet you still look well put-together. Flat sandals are a great way to dress down your pencil skirt for an easy, breezy feel.

Credit: Instagram / marieclairegreece
Flats 3 Flats 3 Flats 3
Sale
Aerosoles Women's Thong Sandal Flip-Flop, NAVY, 5 B (M)
Aerosoles Women's Thong Sandal Flip-Flop, NAVY, 5 B (M)
Core Comfort Technology; Cushioned Footbed; Microfiber Lining
$39.73
Blowfish Bungalow B Desert Sand Dyecut 6
Blowfish Bungalow B Desert Sand Dyecut 6
Spread a little style wherever you go in the stunning Blowfish™ Bungalow B sandals.; Upper made of man-made material with woven detail.

5. Sneakers

For an even more casual look, pair your pencil skirt with sneakers. There are loads of really cute and stylish sneakers that will look great with just about any skirt.

With sneakers, you don’t have to sacrifice comfort for style.

Credit: Instagram / craftfrom_k
Sneakers 1 Sneakers 2 Sneakers 3
Sale
Keds Women's Champion Original Canvas Lace-Up Sneaker, White, 4.5 M US
Keds Women's Champion Original Canvas Lace-Up Sneaker, White, 4.5 M US
Fabric: Canvas; Rubber sole; Ortholite insole; Lace-up at top; Rounded toe
$43.01
JENN ARDOR Women's Canvas Sneakers Low Top Lace-Up Classic Casual Shoes Fashion Comfortable for Walking
JENN ARDOR Women's Canvas Sneakers Low Top Lace-Up Classic Casual Shoes Fashion Comfortable for Walking
[Warm Reminder]: RUNS SMALL NEED HALF SIZE UP. Just message seller if have any problem.
$21.99

6. Combat Boots

This might sound like an off the wall suggestion, but they actually work. Everything in life is about creating a balance. What better way to create balance than to pair an ultra-feminine, form-fitting skirt with something that is the complete, total opposite of everything it embodies?

It’s kind of like having a way to have your cake and eat it too. We all have something inside of us that longs to be able to just be ourselves, even if it doesn’t fit societal norms.

You can do that. Combat boots with a pencil skirt might not solve all of your angst over feeling like you don’t quite fit into the little box you’re supposed to. But here’s a news flash… NO ONE fits into that box. You are not alone – and that’s probably one of the reasons that Doc Martens (though they have never gone out of style) are super trending right now.

Credit: Instagram / opheliajanerose
Combat Boots 1 Combat Boots 2 Combat Boots 3
Dr. Martens Women's Lace Fashion Boot, White Softy T, 9
Dr. Martens Women's Lace Fashion Boot, White Softy T, 9
Retains all the classic Doc's DNA, including grooved sides, heel-loop and yellow stitching
$169.99
Sale
Lugz Women's Dutch Classic 6-inch Chukka Fashion Boot Combat, Wine/Black, 8.5
Lugz Women's Dutch Classic 6-inch Chukka Fashion Boot Combat, Wine/Black, 8.5
Cushioned Insole for added comfort; Synthetic Leather upper; Synthetic rubber outsole, with toecap detail
$34.95

How Can I Hide My Belly In A Pencil Skirt?

Because of the sleek lines of a pencil skirt, it may have a lot of people thinking that a pencil skirt is not for them. After all, how are you supposed to wear one if you have a ‘midlife midriff’? (Welcome to the club!)

Not only are you not alone, but there is a really easy answer to this dilemma – Shapewear!

Shapewear is worn like a girdle, except it’s made of a much lighter material and is much more comfortable to wear. It’s great for keeping things ‘contained’, so you can wear a pencil skirt and hide your belly!

Here are just three examples of shapewear that will give you a flatter midsection so you can rock a pencil skirt.

Shapewear 1 Shapewear 2 Shapewear 3

Take Away

You can read up all you want about what shoes go with this skirt or what color nail polish goes with this dress or what sweater goes with this outfit or how to wear palazzo pants without looking like a circus tent! But at the end of the day, it’s all about what makes you feel good about yourself. 

But at the end of the day, it’s all about what makes you feel good about yourself. 

We are here to help point you in the right direction of what works together. And though we don’t focus specifically on what’s “trending” (because let’s face it – two years from now, it’ll be something else), we want to help you look, and feel, good!

You are the only one who knows how you feel when you put something on. You can look to us for inspiration, but If you find a pair of shoes (or boots) to go with your pencil skirt that’s not on this list that makes you feel amazing – go with that!

Written by Kayla Young

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