How to Wear a Pencil Skirt

Last Updated: March 29, 2022

Pencil skirts are a classic wardrobe staple that can be paired with all kinds of outfits.^{[1]
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Expert Source

Cassandra Sethi
Personal Stylist & Image Consultant
Expert Interview. 31 August 2021.} If you're new to wearing them and not exactly sure how to pull them off, don't worry. We've got everything you need to know about wearing pencil skirts, from choosing a flattering fit to building the perfect outfit. Keep reading to learn how to style a pencil skirt for any occasion.

Part 1

Part 1 of 3:

Choosing the Right Pencil Skirt

1
Fit the skirt to your body. It may go without saying, but when choosing a pencil skirt, you need to make sure that the skirt fits your body well. While most clothing manufacturers size skirts according to the same basic measurements, you still try the skirt on before you buy it.
- If a pencil skirt is too large, it may add too much extra volume to your midsection. As a result, your waist will look wider and your figure may take on a boxy appearance.
- On the other hand, if a pencil skirt is too small, it may create bulges along your thighs, stomach, and rear. Super tight pencil skirts are also difficult to walk in.
- If you aren't sure where to start, try to find a pencil skirt with a waistband that sits roughly 2 inches (5 cm) above your navel. The material should fit around the widest part of your hips without looking stretched, and it should taper off and end somewhere beneath that point instead of ending directly on it.
2
Experiment with length and height. The length of the lower hemline and the height of the waistband will have slightly different effects on your overall appearance. While there are some general guidelines to consider, the best way to determine the right length and height for your figure will be to try on a variety of styles and gauge which one you prefer while standing in front of the mirror.
- If you want to make yourself look taller or leaner, consider choosing a high-waisted style with a shorter hemline. By shifting the skirt further up along your body, you create the illusion of longer legs and a narrower waist.
- On the other hand, taller women may wish to consider pencil skirts that drop down to the knee or just beneath it. You can still show off your naturally long legs with a short skirt, but the added length can have a sophisticated effect when you're tall enough to pull it off.
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3
Play with color, texture, and pattern. Nowadays, pencil skirts are made from a wide range of fabrics and prints. You can stick with classic choices if you want a relatively versatile skirt, but if you're feeling bold, picking something more unique can be a great way to add more pizazz to your outfit.
- It's hard to go wrong with a black pencil skirt, so if you want only one easy-to-style piece in your wardrobe, stick with black. Vibrant colors and prints can be somewhat difficult to dress up, but in comparison, a black pencil skirt can make the switch from professional to casual to seductive much more readily.
- Also note the way that color, pattern, and texture affect your overall appearance. The more you stray from the standard black skirt, the more attention you'll draw to your lower half.
4
Consider your curves. The pencil skirt works well for most body types, but if you're notably curvy on the bottom, you might want to be a little more careful about the way you wear it. Since pencil skirts hug your thighs, they tends to accentuate your lower curves, and the resulting oomph in sex appeal may not be appropriate for all occasions.
- To draw attention away from your lower half, stick with pencil skirts in dark, solid colors and pair them with patterned or textured tops. The visually stimulating top should draw the eye upward, drawing it away from your bottom half in the process.
- Pay attention to the hemline, as well. Make sure that the hemline does not land at the widest part of your thighs; if it does land there, you'll only make the added volume look even more significant than usual. Skirts that hit just above or directly below the knees are usually a better choice since these are the narrowest points of your leg.
5
Try skirts with slits and darts. If you've tried on a standard pencil skirt and don't like the way it fits your curves, don't give up. Try on another pencil skirt with a slit removed or darts sewn into it. Either option will change the shape of the skirt in a subtle way, and it may become more appealing to you.
- To make your hips and legs look leaner, consider wearing a pencil skirt with two vertical darts sewn into the front. The darts draw in your waist and encourage the eye to look up-and-down, rather than side-to-side.
- To accommodate a narrow waist and wider thighs, you might consider a pencil skirt with a 2 to 3 inch (5 to 8 cm) slit in the hemline of the middle backside. The slit gives your legs more room to move around while keeping the waistband cinched in where it needs to be in order to maintain a proper fit. Slits can also give the skirt a sultrier, more flirtatious ambiance.

Part 2

Part 2 of 3:

Building an Outfit

1
Keep it smooth. Since pencil skirts are generally somewhat snug and form-fitting, the wrong underwear can easily create unwanted lines, creases, and folds. For that reason, building the best possible outfit starts with choosing the right undergarments.
- In most cases, any panty style should work as long as the skirt itself fits your body properly. For particularly snug pencil skirts, however, you could consider wearing seamless undergarments or thongs to completely erase unwanted lines.
- To mask unwanted folds, consider wearing some type of shapewear. Girdles and "tummy tuckers" should be able to provide structure to your lower abdomen and upper thigh, which should make the area seem much sleeker and trimmer.
2
Balance the volume. Since pencil skirts hug the curves of your lower body, add volume to your top if you wish to keep your overall shape looking balanced.^{[2]
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Expert Source

Cassandra Sethi
Personal Stylist & Image Consultant
Expert Interview. 31 August 2021.}
- Looser tops should accomplish this task well enough. The key is to look for tops that are meant to drape loosely, rather than opting for tops that are merely oversized, baggy, or boxy.
- Neckline is another factor worth considering. Choosing a top with ruffle or a deep v-neck will make the top half of your body look curvier and more voluminous.
- You can also accomplish this with color. Putting a light or bright color on top will create the appearance of greater volume there, even if the top itself is form-fitting.
3
Determine a focal point. Your pencil skirt can be the focal point of your entire outfit, or you could opt to make another piece the center of attention. It's generally best to stick with only one focal point to avoid making your overall ensemble too busy, though.
- Keep this in mind when picking out colors and patterns. If your skirt has a bold pattern, gravitate toward simpler tops. Conversely, if your skirt is on the mild side, you could spice up your outfit with more vibrant colors, textures, and patterns on top.
- Note that the focal point of your body will be the portion that becomes accentuated. If you want to draw attention to your lower curves or make your legs appear curvier than usual, opt for a patterned skirt. If you want to draw attention away from your lower half, choose a patterned blouse.
4
Tuck in your shirt or leave it out. No matter what type of top you wear, you can choose to tuck it into your pencil skirt or let it hang out. Both options have different effects, so you should make your choice based on the overall look you want to create.^{[3]
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Expert Source

Cassandra Sethi
Personal Stylist & Image Consultant
Expert Interview. 31 August 2021.}
- Tucking your shirt in tends to be preferred. It gives your look a neater, more sophisticated edge. By drawing attention to your waist, this option also makes your legs look longer and your waist look narrower. It also shortens your torso, though, which might be undesirable if you have a petite figure or short waist.
- On the other hand, letting your shirt hang loose will create a more relaxed, easy-going appearance and will also elongate the torso. Using this option with a longer shirt may make your legs seem unnaturally short, though, and loose shirts may make your waist look wider than normal.
5
Pair it with the right belt. If you decide to tuck your shirt into your skirt, consider accentuating the top of your skirt with a belt. As a general rule, choose a belt that's darker than your top and your skirt to make your waist look even narrower.
- You can still wear a belt even if you don't tuck in your blouse, though. Gravitate toward skinnier belts in this instance, and wear the belt directly over your top at the narrowest part of your waist. This can be an especially good fashion choice if you're wearing a loose top since the belt will help you maintain a curvier figure.

Part 3

Part 3 of 3:

Creating Specific Looks

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Wear it to the office. While pencil skirts can look great anywhere, they arguably shine their brightest when worn in a professional setting, like an office or business meeting. Pair a toned-down pencil skirt with other timeless pieces to create a classy, sophisticated ensemble.
- Choose a solid, neutral color for your pencil skirt. Black is an easy choice, but navy blue, brown, tan, gray, or cream could also work. If you really want a patterned skirt, try a fairly muted pattern like pinstripes or houndstooth.
- Pair the skirt with a plain button-down shirt or nice blouse. Consider wearing a ruffled blouse for something feminine yet mature, or something with an interesting print if you want to add a small dose of excitement to your outfit. Tuck the top into your skirt for a well-trimmed appearance.
- Add a blazer for an extra dose of professionalism.^{[4]
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  Expert Source
  
  Cassandra Sethi
  Personal Stylist & Image Consultant
  Expert Interview. 31 August 2021.}
- Keep your shoes and accessories fairly simple. Closed-toe heels are a classic choice, but the right pair of ballet flats could also work. If you wear any jewelry, stick to simple pieces without much sparkle.
2
Spend a night on the town. Thanks to the hip-hugging nature of the pencil skirt, this piece is also sensual enough to wear during a date or a fun night out with friends. Glam it up with other fun, feminine pieces to make the most of this look.
- Nearly any skirt color or pattern can work well as long as you pair it with the right pieces. To boost your sex appeal, though, consider wearing a high-waisted pencil skirt that narrows the waist or a pencil skirt with a tiny slit up the back or the side.
- Your blouse can be anything from simple to shimmery. Try to have fun with it. Nighttime is a good opportunity to play with bold prints, vibrant colors, cropped hemlines, and other edgy trends.
- Pumps and strappy heels are usually the footwear of choice for an evening look, but if your feet can't stand heels, you could swap them out for a fun pair of flats.
- Evening looks are also the best time to play with sparkling jewelry. If sparkles aren't your thing, consider wearing one bold statement piece with an interesting design or bright opaque stone.
3
Keep it casual. The right pencil skirt can also be toned down for a relaxed yet trendy daytime weekend look. Match the skirt with other casual clothes to balance the overall tone of the outfit.
- You can make a black pencil skirt casual, but daytime outfits are a good time to switch out your dark skirts for something in a light or bright shade. Patterns can also work well, but stay away from sparkly, shimmery materials.
- For your top, stick with something fitted yet comfortable. Slouchy sweaters, t-shirts, denim shirts, and similar pieces are all good options
- Your shoes and accessories should be fairly simple. Flats and flat sandals are some of the best choices, and if the rest of your outfit lacks pattern, you can spice things up with more decorative footwear. Simple, non-sparkly jewelry and fabric accessories—hats, scarves, belts—can help you maintain the right tone.
- Go for a tighter top if you want to show off your figure.^{[5]
  X
  Expert Source
  
  Cassandra Sethi
  Personal Stylist & Image Consultant
  Expert Interview. 31 August 2021.}
4
Make it winter-friendly. There's no need to put your pencil skirt away when cold weather sets in. By keeping your legs and arms covered, you can continue to rock nearly any look—professional, evening, or casual.
- Cover your legs with the right nylons. For professional looks, standard sheer nylon tights are often best. Sheer nylons can work for a nighttime look, too, but you can also mix things up by wearing black tights or tights with a slight shimmer woven through them. Casual looks generally do best with colored or patterned tights.
- For your arms, you can either choose the long-sleeve version of whichever top you'd usually go for, or stick with your short-sleeve tops and throw some type of jacket over them. Consider a cardigan or matching blazer for your office apparel. Prepare for a night on the town with a leather jacket, fun blazer, or sparkly shrug. Warm up your casual daytime look with a sweater or denim jacket.
- Remember to wear the right footwear for the season, as well. Cold weather is boot weather. Heeled boots are often good choices for the office or the evening, but flat boots might be a better option when you want something more relaxed.

Expert Q&A

Question

Do pencil skirts look good on everyone?

Cassandra Sethi
Personal Stylist & Image Consultant
Cassandra Sethi is a Personal Stylist, Image Consultant, and the Founder of Next Level Wardrobe, a luxury personal styling service for busy professionals. With over 20 years of fashion industry experience, Cassandra helps people transform their confidence by creating a work wardrobe they love to wear. Cassandra holds a BA in Fashion Merchandising from California State University, Long Beach, and a Postgraduate Certificate in Fashion Buying and Merchandising from the London College of Fashion. She created Soulcycle's retail business and was the Senior Buyer for 90+ Equinox gyms. Cassandra has been featured on New York’s PIX11 in an interview about how to achieve great work-from-home style as well as in Men's Health, Business of Fashion, and NYMag.

Cassandra Sethi

Personal Stylist & Image Consultant

Expert Answer

Oh yes, for sure! Your outfit choices will depend on how tight or loose you want them, but rest assured there’s something for everyone.
Question

How should I dress for curvy?

Cassandra Sethi
Personal Stylist & Image Consultant
Cassandra Sethi is a Personal Stylist, Image Consultant, and the Founder of Next Level Wardrobe, a luxury personal styling service for busy professionals. With over 20 years of fashion industry experience, Cassandra helps people transform their confidence by creating a work wardrobe they love to wear. Cassandra holds a BA in Fashion Merchandising from California State University, Long Beach, and a Postgraduate Certificate in Fashion Buying and Merchandising from the London College of Fashion. She created Soulcycle's retail business and was the Senior Buyer for 90+ Equinox gyms. Cassandra has been featured on New York’s PIX11 in an interview about how to achieve great work-from-home style as well as in Men's Health, Business of Fashion, and NYMag.

Cassandra Sethi

Personal Stylist & Image Consultant

Expert Answer

If you want a figure-flattering outfit, go bold and pair your pencil skirt with a tighter top.
Question

How do you wear a pencil skirt in the winter?

Cassandra Sethi
Personal Stylist & Image Consultant
Cassandra Sethi is a Personal Stylist, Image Consultant, and the Founder of Next Level Wardrobe, a luxury personal styling service for busy professionals. With over 20 years of fashion industry experience, Cassandra helps people transform their confidence by creating a work wardrobe they love to wear. Cassandra holds a BA in Fashion Merchandising from California State University, Long Beach, and a Postgraduate Certificate in Fashion Buying and Merchandising from the London College of Fashion. She created Soulcycle's retail business and was the Senior Buyer for 90+ Equinox gyms. Cassandra has been featured on New York’s PIX11 in an interview about how to achieve great work-from-home style as well as in Men's Health, Business of Fashion, and NYMag.

Cassandra Sethi

Personal Stylist & Image Consultant

Expert Answer

If you need to work with layers to keep yourself warm, consider adding a blazer to your outfit.