What Shoes To Wear With A Pencil Skirt?

Deciding how to style your outfit can be tricky without some extra help. Do you want to wear a pencil skirt but don't know what shoes will match? Not to worry, we're here to help you out.

There are plenty of shoes that go with a pencil skirt. A few of our top finds include:

  • Heels
  • Flats 
  • Sneakers
  • Boots

As we begin, we will discuss all things pencil skirts and show you what shoes to wear with one. Whether you like an athletic look or something more upscale, we've got a footwear idea for you. With that said, let's get right into this topic!

A woman wearing pencil skirt and trendy high heel shoes, What Shoes To Wear With A Pencil Skirt?

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What Shoes Look Good With Pencil Skirts?

When it comes to footwear for a pencil skirt, the options are surprisingly endless. Whether you want to wear your skirt to a fancy dinner, or a simple coffee run, your shoes don't always have to be the same. You can wear heels, flats, sneakers, and even boots with a pencil skirt ensemble from what we found. There is no wrong answer here, but we do have some style options to recommend with a pencil skirt specifically.

Woman wearing pencil skirt and trendy high heel shoes


First, we have an elegant footwear option with a pair of heels. Although they might not always be super comfortable, we love the classic look heels have with a pencil skirt and think they are a great option to try. If you are off to a meeting or even lunch with friends in the city, this is a good footwear idea for you.


Next, we have a good walking option for pencil skirts with simple flat shoes. Generally, this look has a laid-back and business casual aesthetic, perfect for work or a day out. We especially like how effortless flats and pencil skirts pair together and don't fit into one box when it comes to occasion.


Third, we have a casual athletic footwear idea with a pair of sneakers. Usually, we wouldn't think to try this combination together, but it has a great look. If you want to wear a pencil skirt while running errands or even to a sports event, we think sneakers are more than appropriate to try.


Finally, we have a pair of boots to try with your pencil skirt. We think boots are the perfect compromise for anyone not wanting to wear heels and are great for any season. Generally, ankle-length boots look best with a pencil skirt, but you can certainly try a longer style.

How Do You Wear Flat Shoes With A Pencil Skirt?

In general, we recommend you style business casually when wearing flats with a pencil skirt. Like our example above, you can see how flats have a more laid-back look but can still be classed up a bit. Whether you style your outfit for the office or even a day out on a boat, keep it simple and keep your outfit cohesive.

MUSSHOE Ballet Flats for Women

Here we have a pair of pointed-toe ballet flats from MUSSHOE to check out. These shoes have a comfortable memory foam design, promise to be breathable, and come in different color options.

Follow this link to see these on Amazon.

Are Flats Considered Fancy?

If you have an important event to attend and want to wear flats, we say go for it! Especially if you decide on a pencil skirt pairing, you can certainly give it an upscale look. We recommend a long-sleeve blouse or even a blazer jacket to elevate your look while not feeling uncomfortable or underdressed. The key to dressing up is accessories and styling, so throw in a nice piece of jewelry as well.

Zeagoo Women Bow Tie Neck Blouse

Here is a classy bow tie blouse from Zeagoo to try with flats and a pencil skirt. This long-sleeve top is cotton, polyester, and spandex and comes in many different colors.

View this blouse on Amazon here.

POGTMM Women's 3/4 Sleeve Blazer

Here is a blazer from POGTMM to pair with your outfit. This jacket is 100% polyester, washer-friendly, and comes in various color and pattern options.

See it on Amazon here.

Can You Wear Ankle Boots With A Pencil Skirt?

When it comes to wearing ankle boots with a pencil skirt, we recommend it. Like we mentioned earlier, ankle boots have a great look to them when paired with pencil skirts and are a great alternative to heels. Regardless of the season or weather, we think ankle boots are a fashionable and comfortable footwear option with a pencil skirt.

Which Boot Style Goes Best With Pencil Skirts?

Although they might not be your first idea, boots do look good with pencil skirts. When it comes to what style of boots look the best, we say stick to either an ankle-length or a thigh-high. Mid-rise boots will end up cutting off right where your skirt ends, which will make you look shorter. Generally, try to give space between your shoes and skirt so your outfit keeps a cohesive vibe.

Blondo Women's Villa Waterproof Ankle Bootie

Here is an ankle boot from Blondo that will pair well with a pencil skirt. These boots are waterproof suede, have a rubber sole, and come in a few color options.

Check out these boots on Amazon here.

Liliana Women's Suede Pointy Toe Thigh High Boots

Here we have a pair of thigh-high boots from Liliana to see. These suede boots are vegan faux suede, 4.25 inches tall, and have a non-skid sole.

See them on Amazon here.

Can You Wear Trainers With A Pencil Skirt?

If you are after a sporty and comfortable look, we think trainers with a pencil are a good idea. Although this might seem odd to some, athletic shoes with skirts are very "in" right now and are perfect for walking. Whether you want to wear your pencil skirt out shopping or even traveling abroad, we think trainers are a perfect idea.

PUMA Women's Prowl Slip-on Cross Trainer

Here is a slip-on trainer from PUMA to try with a pencil skirt. These shoes are fabric material, have a rubber sole, and come in a few different colors.

Follow this link to Amazon to see them.

Are Sneakers Considered Business Casual?

When it comes to wearing sneakers into the office, we say yes for the most part. Of course, this depends on the setting and your meetings for the day, but usually, sneakers are a good office option. With that said, make sure to choose footwear, sneakers or not, that is neutral in color and not too branded or "blingy." In general, it is a good idea to avoid any clothing or accessories that have huge labels or distracting colors.

New Balance Women's FuelCore Nergize V1 Sneaker

Here we have an office-appropriate pair of sneakers from New Balance. These shoes are synthetic cloth and rubber material, have a memory foam insole, and come in various neutral colors.

See these sneakers on Amazon here.

Can I Wear A Pencil Skirt In The Winter?

For those wanting to wear a pencil skirt in the winter, we give you our blessing. Although pencil skirts are not extremely warm, you can always layer up with tights or leggings to avoid getting too cold. We especially like insulated or thermal tights and leggings and think they will go well with a pencil skirt.

Generally, we recommend trying to style yourself with layers during the winter so you can dress up or down, depending on the current temperature.

Muk Luks Women's Fleece Lined 2-Pair Pack Tights

Here is a two-pack of fleece-lined tights to wear under a pencil skirt. These tights are polyester and elastane, machine washable, and come in a few color combinations.

View them on Amazon here.

What Shoes Do You Wear With A Pencil Skirt In The Winter?

Luckily, your footwear options don't change much for wearing a pencil skirt in the winter. Like our options shown above, anything close-toed is fine for the winter and shouldn't be uncomfortable to wear. Typically, we recommend a pair of pumps, boots, flats, or warm sneakers for wintertime to try with a pencil skirt.

If you don't want to give up your style during colder months, you can always bring a pair of snow boots between home and work and switch into a cuter style once you are indoors.

Columbia Women's Cascara Omni-Heat Snow Boot

Here is a pair of warm snow boots from Columbia to try between home and work. These boots are waterproof, breathable, have a rubber sole, and come in a few color options.

Check them out on Amazon here.

Our Final Thoughts

Whether you wear a pencil skirt to the office or out to lunch, well-styled footwear is essential. From what we found, you can try heels, flats, sneakers, and boots with a pencil skirt, no matter the season. Generally, we suggest choosing shoes on the simpler side for work and brighter colors for other occasions.

When it comes to styling a pencil skirt, we say less is more. Regardless of where you are off to, make sure to find comfortable shoes, and don't be afraid to layer up during the colder seasons!

Still with us? Head on over to these helpful related posts!

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