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7 Different Pencil Dress Styles for the Sleek Dress Style

The pencil dress is one of the classic silhouettes. It creates a long line from your hips to your knees, hugging every curve on the way. The pencil dress has a slimming effect and it can be styled to go anywhere and do anything. You can take the right pencil dress directly from the office to an early dinner date to a night out for cocktails later. Which pencil dress styles should you be wearing and how can you wear these dresses to always look fashionable and amazing? 

Woman wearing a pencil dress

History of the Pencil Dress

The pencil dress was a favorite in 1960s fashion. Look at any movie from the era and some glamorous woman will come strolling into a scene wearing one. But the pencil skirt silhouette actually has its origins way earlier, in 1908. Edith Hart O. Berg was the first American woman to fly in an airplane as a passenger. As fashion legend has it, she tied a piece of rope around her legs, near the bottom of her dress, so the skirt wouldn’t billow up and expose her legs during the flight. In 1908, airplanes were quite a bit more open than they are now. 

Rumor has it that this simple innovation inspired hobble skirt styles, a true oddity in the history of women’s fashion that luckily proved to be only a passing fad. Walking around with a piece of cloth tied around the legs starts to feel and look a little ridiculous on the third step. 

True classic pencil skirt silhouettes did not emerge on the high fashion scene until 1954, though similar slim skirt styles had started to make their way into women’s apparel in the 1940s. 

Types of Pencil Dresses

The form-fitting pencil dress silhouette is really all about the skirt. As long as the skirt hugs those curves and falls at or below knee-length, it’s a pencil skirt. Whether it’s a longer length, including a midi skirt or a maxi dress in a pencil style, doesn’t matter. It’s all about that fit. The bodice that makes up the rest of the dress can be made in any style under the sun. However, some pencil dress styles are more commonly seen than others. 

1. Button up

MakeMeChic Women's Long Sleeve Button Front High Waist Stretch Pencil Bodycon Dress Black and White L

Some pencil dresses are designed with collared button-up looks that are similar to shirtwaist dresses. This is a great style for a professional office look or any casual pencil dress look. 

2. Cap sleeve

Women's 1950s Retro Vintage Cap Sleeve Black Pencil Dress S CL8947-1

Short cap sleeve styles look great with pencil dresses because it creates a balance. This adds a little skin to the overall outfit, as the length of the skirt keeps the legs mostly covered. Pencil dress styles can have any neckline, from V necks to scoop necklines to boat necks. 

3. Crew neck

Dokuritu Women's Short Sleeve Crew Neck Sheath Pencil Dress, Solid Color Twist Front Stretchy Bodycon Dress Black

A more conservative pencil dress may have a crew neck design with short sleeve designs. This can work well for daywear or evening wear, depending on the colour and fabric. 

4. High neck

Yesfashion Women's High Neck Long Sleeve Tunic Bodycon Long Maxi Pencil Pencil Dress Black XL

Pencil dresses made with high neck designs are exactly what you want for a more professional setting. Whether the dress is sleeveless or has short or long sleeves, the high neckline keeps the look perfect for even the most conservative office environment. Remember that more muted colors and neutrals are worn in conservative offices. 

5. Strapless

meilun Women's Rayon Strapless Celeb Party Bandage Pencil Dress (Medium, Blue)

Sexy strapless and spaghetti strap bodices are perfect pencil dress designs for an evening out. This makes a great cocktail dress or semi-formal dress. With the right styling, a pencil dress works as formal attire as well. 

6. Two-piece

Velius Women's Scoop Neck Neon Bodycon Two Piece Pencil Maxi Dress Clubwear Outfits (White, Medium)

Create a pencil skirt outfit that looks like a dress by matching a blouse to your pencil skirt. Some pencil dresses are made in two separate pieces so you can bare a little midriff or mix and match your different outfits with separate tops and pencil skirts. Match the colors and the patterns to make your own DIY pencil dress, at least in appearance. You can also mix it up by trying a contrasting look, such as pairing a white shirt with a black skirt. Play around with separates when you’re looking for outfit ideas.

7. Wrap

GRACE KARIN Women's Bodycon Pencil Dresses for Work Wrap V Neck Business Dress with Belt Pink Black M

Even in pencil dress designs, the wrap dress style is hugely popular. The wrap bodice is extremely flattering to the bustline. A form-fitting wrap pencil dress will show off those curves and lines quite well and help you make the most out of your figure. 

Fabric Used for Pencil Dresses

Pencil dresses are literally made in every type of fabric. Wool, tweed, linen and cotton are used for more casual or office-friendly looks. A denim pencil skirt is perfect when you want to create a casual but stylish pencil skirt outfit. Silk, leather and synthetic fabrics are typically seen in more cocktail-ready designs. Extras like lace, satin and knits are most commonly used in semi-formal and formal looks. 

Because the silhouette of this dress is so iconic and because the dress can be made with any different bodice style, the pencil dress is easy to make and easy to shop for anywhere. It always looks good. When you’re in doubt about your fashion, reach for a great pencil dress, grab a clutch and slip into some matching heels. You will literally be well-dressed for any occasion…unless you’re going to be hiking. Heels and a tight-fitting skirt are not the greatest for hiking. Otherwise, you’re going to be a total fashion plate. 


Still have questions about wearing a pencil dress and styling it the right way? We’ve got the answers to all the most commonly asked questions about pencil dresses. Get the answers and get your pencil dress style looking spot on and highly fashionable everywhere you go.

What color pencil dress best suits your skin tone?

The color of clothing you wear has a huge effect on how you look overall. If you’re going to slip into a pencil dress, wear one that’s going to suit your natural coloring. The rule of fashion is that if your skin tone is warm, wear warm colors. If your skin tone is cool, wear cool colors. The shade of the skin and the shade of your hair have nothing to do with whether you’re warm or cool. It’s all about the undertones of your skin.

There is a simple way to determine whether you’re a warm or a cool. Stand in natural lighting and take a look at the inside of your wrist. Do the veins look blue or purple in color? If so, you have a cool skin tone. If the veins look more green in tone, you have a warm skin tone. If you just really can’t tell, you probably have a neutral skin tone. You can play around with any colors you want.

Warm skin tones look great in warm colors. Earth tones in brown and red, pink, orange, gold, copper, yellow and any color that has a warm tone to it will look great on you. Black pencil skirt looks and white also work very well on warmer skin tones. Gray, tan and beige tones work great with warm tones as well. 

Cool skin tones are beautifully set off with shades of green, blue and purple. Icy color tones and pastels are perfect, along with cool jewel tones like sapphire blue and emerald green. Rich yellow, orange and red tones aren’t going to work as well. 

Neutral skin tones are best set off in more neutral or muted colors. Dark colors, like navy and maroon, work well. Deep jade, gray, black, off-white and black all work well. 

Can you wear a pencil dress casually?

Pencil dresses are great for casual wear.  They look perfect on a day date or a day out running errands. Look for dresses made in cotton, linen or wool fabric when you’re looking to create a casual look. A skinny belt or a button-up cardigan sweater is a great way to make a pencil dress look more casual. Pair it with wedges, flats or sandals to complete a cute casual look that’s ready to go anywhere. 

How do you wear a pencil dress in the winter?

It can be tricky to wear a dress in the winter but some occasions and events just call for it. When you need to be stylish but you don’t want to freeze, get lever about how you’re going to style a pencil dress. The longer length of this dress makes it great for fall or winter wear. As long as you know how to style it, a pencil dress can work well in the winter. 

Wear a slip under the pencil dress to add an extra layer of warmth, because every bit of insulation helps. In that vein, add stockings. Thick woolen stockings will keep legs nice and warm in winter. If you’d rather avoid stockings at all costs, wear tall knee socks and high boots. The boots and socks will help protect your legs. Top it off with a long overcoat that’s nice and thick. 

Do pencil skirts and pencil dresses look good on everyone?

Because of the form-fitting cut and the length of the dress, pencil dresses don’t necessarily perfectly flatter all body types. Some body types are better displayed in pencil dresses than others. Pencil skirts are great on rectangular or athletic bodies that aren’t highly curvy and have more straight lines, but they’re also highly suited to the super curvy hourglass shape.

Pear shapes and apple shapes benefit from dresses with a more flared skirt. For this body type, try something more flared like a swing dress. A body shape that is rounder at top or bottom is tricky to dress in a pencil dress or any other close-fitting skirt style. Even a high waisted pencil skirt will be hard to style. An a line skirt that has more flare to it, however, will work great on these body shapes.

What to wear with a pencil skirt or pencil dress?

Pencil dresses can be styled to look casual, professional, semi-formal, sexy or even formal. It all depends on your accessories. With a structured jacket, a pencil dress looks professional. Top it off with a button-up shirt tied at the waist and it’s adorably casual. This is a classic look that’s easy to create with any unique or traditional pencil skirt, from a simple polyester blend to a hot black leather pencil skirt.

Wear it with heeled boots and a faux fur coat to look totally glam. Slip into stilettos and chic statement earrings for a sexier cocktail dress look. Add a cropped jacket and sneakers to add an edge of casual style. A sleek leather or satin jacket can make a pencil dress look great as an evening look and get you red carpet ready.

A denim jacket adds casual glam to the dress. A jacket or an extra layer is a perfect accessory for a pencil dress when you want to be able to transition easily from a day to an evening look. That’s why the pencil dress is such a great choice when you want to create fashionable, timeless style.

Pair your pencil dress with high heels, sandals, wedges or any other type of footwear you like.