How to Wear a Pencil Maxi Skirt

How to Wear a Pencil Maxi Skirt
Discover how to style pencil maxi skirts for various occasions, from formal office wear to casual gatherings, by coordinating tops and accessories effectively.

If there’s a garment that has stood the test of time and trends, it is the pencil skirt. It’s been 70 years since fashion guru Christian Dior introduced the modern pencil skirt, and it’s still an unrivaled wardrobe staple for most women, especially in the business world.

The history of the pencil skirt we know today however started off in the form of a maxi skirt. In 1908, Mrs. Edith Hart became the first woman to board an airplane as a passenger, accompanying her husband’s friends Wilbur and Orville Wright. The two were worried that her long billowing skirt would get caught on the machinery, so they tied it with a cord around her ankles to keep it intact.

This inspired the creation of the hobble skirt-the pencil skirt ancestor-which required women to take short steps and wiggle their hips while walking to avoid tripping. Dior solved this problem with his H-collection, which was straight length-wise instead of being too tight around the lower legs. In fact, modern pencil skirts even come with a slit to make walking easier, and some even have pockets.

Dior’s version was also mid-length, not maxi-length, as we all know. That said, pencil maxi skirts have always given their midi-length counterparts a run for their money. In fact, they are the most popular skirt among hijabi women because they are stylish, modern and modest at the same time.

I also find pencil maxi skirts more versatile than their midi version because they look less professional. You can dress them up for work, events, or down with sandals and a crop top for a beach party or grocery shopping.

But enough with the history.

How do you wear or rather style a pencil maxi skirt?

The best way to do this is by occasion.

Formal Pencil Maxi Skirt

Choose a dark-colored pencil maxi skirt and pair it with a neutral formal-looking top. A long-sleeve top, short-sleeve camisole, or a blouse tucked in and paired with pointed-toe pumps is a great ensemble if your office is relaxed. If it gets chilly, you can then throw on a structured blazer, a trench coat or even a shawl.

But if you want to be really formal, a button-down shirt or blouse is the perfect choice. Tuck in the shirt, add a belt to the skirt and carry a formal purse. A blazer on top of this is okay but not a must.

Does that mean you can’t wear other colors of pencil maxi skirts to work? No. While black is the best option, other dark colors like olive green, beige, gray, burgundy and blue are good too.

Semi-Formal Pencil Skirt

The best semi-formal way to rock a pencil maxi skirt is by wearing a colored one. Let’s leave black for the office. For example, this fuchsia pencil skirt paired with a simple tee and pointed-toe pumps speaks elegance but not in a formal way. You can rock this to a wedding, date, daytime meeting or family gathering.

I also recommend a skirt with fun details like this one with a high waist and side panels- perfect for weddings and events. To add the casual effect, switch the pumps with boots and wear a long sweater or trench coat over the top.

My friend Alexandra Golovkova, who by the way has a company that makes pencil maxi skirts, has other styling options for our Muslim and other hijabi friends, but all women can copy them. My favorite among them is wearing a sweater tucked at the front and stilettos or boots, depending on the weather.

How about this front-slit leather pencil maxi skirt paired with a button-down shirt and stilettos? It is bound to turn heads, and you can attend meetings and classy events with it. You can also soften the look with a sheer chiffon blouse instead of a formal shirt.

We have a whole guide on styling leather maxi skirts here.

Casual Pencil Maxi Skirt

Your options for a casual pencil maxi skirt are plenty, and again, it depends on what you are dressing for.

If the plan is to attend a casual party with close friends, a crop top and heels will be perfect. I love these monochrome ensembles you can rock to any party or evening event, looking like a fashion bombshell.

But if you want to run errands, meet family or go to church, a tucked-in t-shirt, slim belt and sandals or sneakers will do the trick. You can wrap a scarf for good measure or throw on a cool jacket- denim, leather, or mojo jackets are still very much in style.(The Complete Guide for Jackets To Wear With Maxi Dresses)

Alternatively, rock the sweater-pencil skirt combo where you tuck the sweater at the front and wear a simple pair of sandals or sneakers. A cropped hoodie also works amazingly well with a pencil skirt, and you can wear a jacket over it for warmth.

Final Thoughts

The bottom line is that styling pencil maxi skirts is pretty easy whether they are leather, formal or casual. The trick is to figure out the occasion and find a top or outer garment that matches that. The weather will also determine whether you wear a crop top on a casual day or a turtleneck and hoodie.

What do you wear with a long pencil maxi skirt?

Ideally, you should wear a top or outer garment and shoes that fit the occasion. For instance, if you wear the pencil maxi skirt to work, a button-down shirt, blouse or a long sleeve top with a blazer are good options. For casual wear, you can try a tank or crop top, sweater and casual shirts, including a denim shirt complete with sneakers, boots or sandals.

How do you style a pencil maxi skirt for parties?

A monochromatic combination featuring a bright-colored pencil skirt and matching crop top is ideal. Finish this with a pair of stilettos, a trench coat or poncho for later when it’s cold and a classic clutch bag.

Lior Shapiro

I love clothes with pockets and dresses, and I think any woman can pull off a good maxi dress.
I believe women's clothes with pockets make the world a better place.