A pencil skirt is a type of skirt that has a fitted waistband and is made from light fabric (usually chiffon) with a full skirt that hangs to the mid-calf or below. Pencil skirts are often straight, pleated, or gathered at the waist to give them shape. They became popular in the 1950s and 1960s, but they have been seen across numerous decades.
Pencil skirts look professional without being too square. A pencil skirt will instantly put some polish on whatever outfit you’re wearing because it looks pulled together without looking stiff. They’re versatile, forgiving, and fashionable enough for a casual Friday but still polished enough for the office. A pencil skirt is a great staple to have in your closet, dresser drawer, or wardrobe. It’s easy to throw it on and go since it can be dressed up or down. It’s not just for women either; men can wear pencil skirts too that are stylish, trendy, and professional as well. From workwear to formalwear, they’re a one-and-done item that can be worn with everything from dresses to skirts to pants to joggers.
You’ll get many outfits out of a pencil skirt outfit. It can be worn with almost any top or bottom, and it’s a piece that you’ll wear over and over again. It’s so versatile because it can be dressed up or down depending on the occasion. Wear a pencil skirt with a tuxedo jacket to make the skirt more casual during the day or nighttime, wear a leather pencil skirt with a dress to make the outfit more formal. Try pairing a pencil skirt with straight-leg pants or black wide-leg pants for a casual ensemble that looks just as great at work as it does at dinner after work.
Table of Contents
- 1. The Office-to-Happy Hour Outfit
- 2. The Office-Casual Outfit
- 3. The Breakfast-With-Clients Outfit
- 4. The Weekend Outfit
- 5. The OOO Outfit
- 6. Pencil Skirt with a Denim Shirt
- 7. Pencil Skirt with a Red Shirt
- 8. Pencil Skirt with Belt and a Sheer Shirt
- 9. Denim Pencil Skirt with a Plain White Tank
- 10. Lace Pencil Skirt with a Denim Shirt
- 11. Patterned Pencil Skirt with a Denim Shirt
- 12. Pencil Skirt with a Blazer
- 13. Pencil Skirt with a Crop Top
- 14. Pencil Skirt with a Funky Top
- 15. Pencil Skirt with a Lace Top Underneath the Blazer
- 16. Pencil Skirt with a Colorful Sweater
- 17. Black Pencil Skirt with a White Shirt
- 18. Leather Black Pencil Skirt with High Heels
- 19. Leather Black Pencil Skirt with Cardigans
- 20. A Lace Pencil Skirt
- 21. A Zipper Pencil Skirt with Shirt
- 22. Pencil Skirt with Trench Coats
- 23. Animal Prints Pencil Skirt
- 24. Pencil Skirt and a Plain Crop Top
- 25. A Powerful Flower Pencil Skirt
- 26. A Black and White Pencil Skirt
1. The Office-to-Happy Hour Outfit
Invest in a black pencil skirt if you work in a more corporate environment. Although the bottom is a little plain, think of it as a blank canvas for a beautiful floral top or a vivid handbag. You could even be able to get away with wearing a pair of trendy open-toed sandals that aren’t in the HR handbook. This bottom can effortlessly transition from work to happy hour on any weekday with the appropriate accessories.

2. The Office-Casual Outfit
Give this tiger print pencil skirt a try if you have more freedom at your 9-to-5. It makes a statement, which is why you should pair it with a basic white blouse, gold hoop earrings, and black slides to keep it understated. You might want to wear this look again on the weekend (swap the tee for a sleeveless crop top). This outfit is a win-win that’s trendy and professional.

3. The Breakfast-With-Clients Outfit
This vibrant floral printed skirt is a terrific way to mix up a simple shirt and jacket for meetings when you want to look professional but not stuffy. In addition, the skirt is a great conversation starter, and you’ll get a lot of positive feedback. Add a structured accent like this crossbody bag and slingback heels for a sophisticated look.

4. The Weekend Outfit
Swap your shoes for sneakers and a classic pencil skirt for a more relaxed denim version on Saturday. (The middle side slit is NSFW.) Instead of a jacket, wear this tie-dye turtleneck, which is warm enough to take you from the end of summer to the beginning of fall. If you’re feeling frisky, pair it with a Chloé bag and some ballet flats.

5. The OOO Outfit
When you take that much-needed PTO, bring this pencil skirt with you. It features the same structure as your typical 9-to-5 outfit, but with more sultry accents like side ruching and a high-rise slit. The colorful blooms also transport your senses from your office and distant beaches. Replace your work tote with a smaller, prettier purse and a floral bucket hat to complete the look.

6. Pencil Skirt with a Denim Shirt
Pair your pencil skirt with a denim blouse and nude heels to achieve the best neutral lifestyle. This sparkling combo is completed with a clutch. You can wear this look to work or out on the town. In addition, this fashionable style can be a decent look for a breakfast meeting.

7. Pencil Skirt with a Red Shirt
Choose a redshirt for a pop of color and a striking necklace to complete your look. In no time, you’ll be looking professional and stylish. A women’s pencil skirt is an essential staple of any wardrobe. It can be dressed up or down and can complement a variety of tops, such as white shirts. But what if you want to wear your pencil skirt to work? One option is the classic look: wear a chambray shirt with it. Try an animal print top instead to spice things up a little bit.

8. Pencil Skirt with Belt and a Sheer Shirt
A feminine look may be achieved using a sheer shirt and a decorative belt, which is ideal for a first date. Heels are required. The pencil skirt, one of the most versatile pieces of clothing in any woman’s closet, can be dressed up with a belt and shirt. The combination offers a streamlined look that is perfect for the office or the night out. If you want to feel more attractive than usual, pair this ensemble with your best heels.

9. Denim Pencil Skirt with a Plain White Tank
A denim pencil skirt, especially worn with a plain white tank, can certainly turn heads if you’re searching for something edgier. However, if you’re more traditional, go with a straight pencil skirt in black or brown. This is an easy way to game the system and still look professional in your office attire.
The denim pencil skirt is one of our favorite wardrobe staples for women on the go, but it’s also the most versatile garment in any woman’s closet. No matter what work environment you find yourself in, this skirt can shift quickly from day to night when paired with just the right top and accessories. The key here? Find pieces that will play up your style while at the same time exuding professionalism.

10. Lace Pencil Skirt with a Denim Shirt
This stunning lace pencil skirt is toned down with a denim shirt to create a stunning look. Since we’re on the subject, a pair of nude pumps is also a must-have item for any fashionista. They complement practically any outfit.

11. Patterned Pencil Skirt with a Denim Shirt
Another fantastic pairing of a patterned pencil skirt and a denim blouse. As you can see, keeping the upper half simple allows the skirt to make a stronger statement. You don’t want to wear too many patterns when you work. Although I would not wear one of these with a suit, I like imagining what it would look like on someone at the office. Perhaps you could have the skirt done in solid colors and pair it with a blazer, or a dressy shirt, like this one from J. Crew. This combo works exceptionally well when you have some color in your outfit and struggle to find something that works.

12. Pencil Skirt with a Blazer
After work, do you have a date or a cocktail party planned? It’s no problem! Although this top isn’t acceptable for the office, it goes well with the skirt and will look amazing with a blazer. Remove the blazer when you leave the office and instantly transform your style without having to go home and change.

13. Pencil Skirt with a Crop Top
The style is swoon-worthy, and the fashion is a reoccurring trend of the fall season. Fall style takes its cues from the upcoming winter; it’s not just about mullets and flannel anymore. A pencil skirt with a crop top combo provides a valuable option for autumn days (and nights) that are less than cold. It’s great for those office days when you’re leaving at 5 pm and looking to make an impactful exit! This sultry evening wear look manages to be cutesy and professional, perfect for dressing up work attire in this transitional period.

14. Pencil Skirt with a Funky Top
To add a slight edge to your pencil skirt, pair it with a unique top. Just be careful not to make the outfit too far, or you can quickly look like a cartoon character. Whatever your style is, there’s sure to be a graphic tee your can pull from your wardrobe to complete the look. An outfit consisting of a pencil skirt and graphic tee will give off just enough edge without being too over-the-top for work. Check out this list of stylish options that are perfect for any occasion!

15. Pencil Skirt with a Lace Top Underneath the Blazer
As part of a power suit, pencil skirts look fantastic. Underneath the blazer, wear a lace top to soften the style and show off your femininity. Make sure to pair the skirt with an all-black suit for a chic and striking look. What could be better than wearing a pencil skirt? Pair it with another feminine piece, like a lace top, for business-appropriate style. Wear your skirt as part of your work ensemble, or toss it on with jeans and casual attire when you want to go out in the evening. Either way, this piece will be practical and stylish!

16. Pencil Skirt with a Colorful Sweater
Pencil skirts are appropriate for all seasons. They look great with tights, boots, and a bright sweater in the fall. A classic black skirt with a jean jacket looks fabulous for the winter. You can keep them simple with a tailored pencil skirt paired with a sheer blouse and kitten heels in the summer.

17. Black Pencil Skirt with a White Shirt
A black pencil skirt is an introduction to corporate attire, but it has the advantage of being more formal than a pencil skirt in another color. It is also an excellent choice for today’s “business-casual” environment. This article of clothing complements a white shirt, and with a dressier blazer or sweater added to the ensemble, you have a component of your work wardrobe that can go anywhere.

18. Leather Black Pencil Skirt with High Heels
Even if you don’t have Blake Lively’s curves, a faux leather black pencil skirt looks great on any figure. When you wear a skirt with high heels, your legs will appear longer. This skirt is an easy, one-piece uniform that would look great with a simple sweater, a blazer, or even an open cardigan. The material is made of faux leather, which means it breathes. You can wear this skirt to work as well as for everyday use.

19. Leather Black Pencil Skirt with Cardigans
When it comes to what to wear with pencil skirts, blazers are all the rage, but cardigans can also work. You can wear a blazer over any pencil skirt and pair it with a cardigan to create a professional and fashionable look. For an office-appropriate outfit, opt for navy, black, or grey. For a night-out look, choose colors such as plum or purple. Then, layer with simple necklaces, your favorite earrings (if you’re wearing the right color), some strappy heels or boots, and you are good to go!

20. A Lace Pencil Skirt
This is a perfect outfit for a professional woman because it’s stylish and sexy. In addition, it makes a strong statement because lace skirts are hard to find in the workplace. If you want to make your workday more enjoyable, I suggest choosing this outfit! It will make your work environment feel brighter and more lighthearted. In other words, you’ll be able to enjoy help at work without feeling as though you have to wear a boring uniform.

21. A Zipper Pencil Skirt with Shirt
It’s the most versatile work outfit there is. This is a skirt that can be worn on any occasion and with any shirt you have in your wardrobe. I find it easiest to dress this up or down depending on what I’m wearing or what the occasion calls for.

22. Pencil Skirt with Trench Coats
A warm and inviting design for those drizzly autumn days. Pencil skirts look nice with trench jackets. For a more industrial look, wear a striped shirt.

23. Animal Prints Pencil Skirt
Whether you’re looking for a skirt as part of a work outfit, formal evening wear outfit, or as weekend wear, the animal prints pencil skirt is the way to go.

24. Pencil Skirt and a Plain Crop Top
The pencil skirt is always seen as the smart girl’s go-to for work, but it can be tricky to mix and match tops with this piece without looking too plain or just downright dull. That’s why we’re taking on the challenge of exploring how you can wear a pencil skirt in the office without wearing the same top each day. You might be tempted to pick up one of these super cute crop tops that are in style at the moment, but when you’ve got a job where you need to look competent and professional, there is no time for messing around…

25. A Powerful Flower Pencil Skirt
It is a staple piece of the pencil skirt outfit. This item is a great way to add flavor, color, and creativity to your work outfits. It will give your look something new and innovative that you can wear with anything in terms of the top (a white t-shirt or blouse), jacket, or other skirt items. The following article provides some ideas on putting these pencil skirts together for an easy day at work!
A flower skirt can be a great way to make an easy work outfit feel like a chic fashion statement without much extra effort. All you need are some solid basics for the rest of your ensemble, and then accessorize with this one powerful piece of clothing.

26. A Black and White Pencil Skirt
The black and white pencil skirt is also known as a sheath or a straight skirt. Pencil skirts give the impression that the woman is very lean and slim. They are often worn with either a sweater or jacket on top and sometimes with heels. The black and white pencil skirt is one of the most classy and elegant ways to wear this item of clothing while still maintaining some femininity in the outfit.
