9 Best Shoes To Wear with a Pencil Skirt (For Stylish Outfits)

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Got a pencil skirt lying around in your closet that doesn’t get enough use? It’s time to bring it out! Here’s a style guide on the best shoes to wear with a pencil skirt.

Pencil skirts are synonymous with corporate settings and office wear, but they don’t need to be. Pencil skirts hug the figure, which is perfect for any body type or body shape (especially if you want to flaunt your curves), and we think they deserve a little bit more love.

Get this skirt on Princess Polly

Did you know that there are so many different casual styles and lengths of pencil skirts that can be worn for the beach, for shopping, for going out, and lots more? With so many different sub-categories of pencil skirts, it can be difficult to decide what shoes to wear to complete your look.

So, in this article we will explore 8 different shoe options that will help you look your best, whether it’s for business at the office or for leisure someplace else.

The Best Shoes To Wear With Pencil Skirt

1. Pumps

The Best Shoes To Wear With Pencil Skirt: Nude pumps
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 A classic choice, pumps are the perfect way to add a touch of sophistication to your entire look. They come in a variety of colors and styles, so you’re sure to find the perfect pair for you.

Style your black pencil skirt with a nice crop top and a pair of sultry black pumps for chic going-out outfit. If you’re going to a business meeting, no worries – simply swap out the crop top with a long-sleeve shirt or a white blouse. To elevate your look even more, add a neutral blazer for a stylish look.

2. Stilettos

The Best Shoes To Wear With Pencil Skirt: Strappy black stilettos
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If you’re looking to add a little bit of height, stiletto heels are the perfect choice. They can be worn for both business and pleasure, making them a versatile pair of high heels.

These shoes can take your outfit from day to night with ease. For a party look, wear your black leather skirt with a pair of strappy heels and a fitted top of your choice.

3. Ankle Boots

Black ribbed pencil midi skirt
Get this skirt on Beginning Boutique
The Best Shoes To Wear With Pencil Skirt: Velvet black ankle boots
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If you’re looking for the best shoes to wear with a pencil skirt in the colder months, ankle boots are definitely the way to go. Not only will they keep your feet nice and warm, but they’ll also add a touch of edge to your look. For a chic alternative look, pair your graphic tee with a classic pencil skirt and your choice of ankle boots.

Alternatively, you can switch ankle boots for flat or heeled combat boots if that’s more your style.

4. Sneakers

The Best Shoes To Wear With Pencil Skirt: White sneakers
Get these white sneakers on Lulus

If you’re searching for the best shoes to wear with a pencil skirt but you don’t want to sacrifice comfort, then go for flat shoes like a pair of sneakers. You can find some really cute and stylish pairs that will look great with just about any skirt.

Make sure to wear clean, sleek sneakers, unless you’re going for a particularly casual aesthetic. Complete your outfit with a coat or a black leather jacket.

5. Knee High Boots

Black suede knee high boots
Get these ankle boots on Lulus

Knee high boots are the perfect choice if you want to make your look a bit sultrier. Tall boots can be worn with skirts of all lengths, and they’ll keep you warm in the colder months. (Pro tip: if you’re pairing these with a pencil maxi skirt, make sure there’s a high slit to show off your boots!)

For a cute fall look when going out shopping, wear a black leather pencil skirt with a pair of black suede boots. Complete the look with a chic sweater on top, or a long-sleeve blouse of your choice.

6. Flat Sandals

Tan flat sandals with gold details
Get these flat sandals on Lulus

If you want the best shoes to wear with a pencil skirt during the summer months, flat sandals are the way to go. Not only will they keep your feet cool, but they can also add a touch of glam, especially if you’re opting for a pair of metallic sandals, or a designer pair like the Miller sandals from Tory Burch.

Flat sandals are a great choice especially if you’re going out on a day trip with lots of walking. The sandals will give your feet room to breathe, and you’ll look chic at the same time.

7. Ballet Flats

Animal print ballet flats
Get these shoes on Lulus

Ballet flats are a great choice for a subtle, elegant look. Plus, simple ballet-style flats are super comfortable, especially if you want to look professional without having to wear a pair of heels.

You can find ballet flats in a variety of colors and styles, so you’re sure to find the perfect pair for you. Just be sure to avoid any that have too much embellishments if your outfit is already particularly busy.

8. Mary Janes

The Best Shoes To Wear With Pencil Skirt: Tan suede Mary Jane platform heels
Get these Mary Janes on Lulus

If you’re looking for shoes that are particularly trendy, Mary Janes and other similar platform heels are the way to go. You can find them in a variety of colors and styles, and compared to other high-heels, they’re quite comfortable to walk in.

Mary Janes come in different heel heights (flats, platforms, heels), so you have many options to choose from. For a cute light academia look, wear a white pencil skirt or plaid skirt with a pair of platform Mary Janes. Be sure to wear some sheer tights underneath if the weather is cold, and cover up with a beige trench coat.

9. Espadrilles

The Best Shoes To Wear With Pencil Skirt: Black lace-up espadrille wedges
Get these espadrille wedges on Lulus

Lastly, for a super cute summertime look, you can never go wrong with espadrille wedges. Espadrilles are the perfect choice if you’re wearing a pencil skirt with floral prints or bold patterns. They’re great for outdoor events by the beach, or sunny day trips out with your friends.

Espadrilles come in flats or wedges, you can choose what heel height is best for you.

Commonly Asked Questions

Why are pencil skirts called pencil skirts?

The name “pencil skirt” is derived from the shape of the skirt, which is slim and straight like a pencil.

How do you style a pencil skirt for work?

If you want to wear your pencil skirt for work, we recommend pairing it with a button-down shirt or blouse. For shoes, closed-toe heels are always a good choice. If you need to walk during a typical work day, consider wearing flats or loafers instead.

Are pencil skirts still trendy for 2022?

Pencil skirts are timeless wardrobe staples and definitely still trendy in 2022. If you want to stay ahead of the curve, try opting for a printed or patterned pencil skirt instead of a solid color. You can also experiment with different lengths – mini, midi, and maxi skirts are all on-trend right now.

What body shape can wear a pencil skirt?

Most body shapes can wear pencil skirts, but they’re especially flattering on women with an hourglass figure. If you have a pear-shaped body, try pairing your pencil skirt with a blouse that has ruffles or other details around the bust to balance out your hips.

And there you have it, the best shoes to wear with a pencil skirt! We hope you found this list helpful. If you’re still looking for more fashion inspiration, be sure to check the posts down below.

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