How to Wear a Pencil Skirt

By on April 15, 2015

A pencil skirt is a thin, leg hugging skirt, that often has a slit, or pleat to allow a better range of movement. Created in the 1950’s by Christian Dior, the goal was a feminine body-hugging design. The original design often made women move quite a bit when they would walk, so over the years the skirts evolved to include a slit up the back or side to give some ease of movement. The goal was to draw attention to the hips, rather than the waist. This makes it an ideal skirt for any body type.
The pencil skirt acquired its name because it was a slim, form fitting cut, created specifically to draw attention to the femininity of the woman wearing it. When worn below the knee, even with a slit or pleat, it can be hard to walk in, as it will be much more constricting than most other styles of skirts, but this is what makes it so feminine as it forces women to make smaller steps.
It often takes some practice to wear a pencil skirt due to the tight nature that restricts movements. This can make it difficult for a woman to get in and out of a car with grace. One advantage is that during cold weather, it’s warmer, and the wind is not able to lift it up and flash potential bystanders. (Think Marilyn Monroe!)
When you choose to wear a pencil skirt, make sure you go longer then the fingertips/knees for a more formal setting. Shorter pencil skirts can be worn casually, or for dates. But traditionally the pencil skirt works in a business or formal setting because it covers all your parts, while alluding to how feminine your figure is.

Your size, shape and figure also play a part in how you pick a pencil skirt
Take into consideration your figure shape and size as well. Go up a size and have it custom tailored if your bottom is heavy. Make sure to look at your skirt from the side, as you don’t want a pooch, try using a body shaper if needed to make a clean line. The ability to use a body shaper allows a woman of any shape or size to wear a pencil skirt with class; however a big bottom needs to be taken into consideration, as not all skirts will fit proportionally and you may also need to custom tailor a larger size to fit your waist.
Your height also plays a part. Ensure that you pick the right length of skirt for what you are choosing to do and how tall you are. Make a decision on shirt tucked in, or tucked out. A shorter woman, who wants to look taller, or draw attention to her line, may choose to wear a tucked in shirt, where-as a taller woman may want to downplay her height and leave her shirt un-tucked.

How to wear a pencil skirt for work

  1. Clean lines.
Angelina Jolie

Angelina Jolie

Keep your lines cleans by using a body-shaper under the outfit. Wear a black pencil skirt with a white blouse and blazer. Use pumps and pair it with a matching shoulder bag, or briefcase.

  1. White skirt.
Jennifer Lopez

Jennifer Lopez

Black pencil skirts are generally considered office wear, but consider a white pencil skirt, paired with the right top and shoes instead. White skirts can work, just use that to highlight your outfit instead of your top and shoes.

  1. Use a belt.


A knee length pencil skirt, with a brown belt and white shirt are always a winner. Just make sure you match shoes to the outfit so you don’t look too casual. Heels and pumps are a winner here; avoid sneakers, sandals and less dressy shoes.

  1. Gray pencil skirt.
Kim Kardashian

Kim Kardashian

Consider a grey pencil skirt. This is so versatile, that you can really dress up the outfit with your shoes or top to complete the look. You can also pair it with a sweater, or a blazer.

  1. Blue skirt.
Olivia Palermo

Olivia Palermo

Blue pencil skirts are a good choice with sweaters, and brown belts. Wear a white blouse to complete the look. This works well with your hair up in a bun.

How to wear a pencil skirt on a date

  1. Sheer top.
Kim Kardashian

Kim Kardashian

A long hugging pencil skirt, paired with a see through top and black bra scream sexy, and is perfect for an intimate date night for two. Add in some red high heels, and gold or silver jewelry to complete the look.

  1. Leather skirt.

7Now that pencil skirts come in a huge variety of fabrics, you can try wearing a leather one, with a sexy top, some heels and a cute shoulder purse.

  1. Crop top.


A long leather skirt, mixed with a crop lace top that shows cleavage, paired with a tall pair of sex high heels is always a winner.

  1. Corset.


A pencil skirt with a corset is always a winner too. Feel free to experiment with different colors and different styles of heels to find the perfect look for you and your body shape.

  1. Chameleon.


Throw a waist-binder corset in your car, so you can go straight from the office secretary in your pencil skirt and blouse, to hot dinner date in a matter of seconds.

How to wear a pencil skirt casually

  1. Sneakers.
Karolina Kurkova

Karolina Kurkova

Sneakers are a great way to downplay the formal look of the pencil skirt. This may also help you walk better if you are having trouble walking in high heels with the way the skirt confines movement.

  1. T-shirt.


Wear a simple T-shirt and let the skirt do the talking for the outfit as the feminine touch. Consider bold colors or prints for your pencil skirt, paired with brown sandals or heels. Dress up the outfit with cute hairstyles, headbands, and earrings.

  1. Jean jacket.
Rosie Huntington Whiteley

Rosie Huntington Whiteley

Throw on a jean jacket with a plain colored pencil skirt; you can also wear a short mini pencil skirt to show off your legs. To switch it up, wear a baseball hat, or sneakers to show off your fun casual side.

  1. Romantic.
Jamie Chung

Jamie Chung

Try a floral pattern paired with strappy sandals and a cute plain colored peasant blouse. Bracelets and chunky necklaces look great with floral prints. If you want a fancier print for your shirt or blouse, make sure you use a plainer color or print for your skirt.

  1. Mini pencil skirt. 
Kendall Jenner

Kendall Jenner

Consider ankle boots, a mini pencil skirt and a crop top. You can accessorize with a shoulder bag and a light-weight sweater jacket. You can also use a plain colored pencil skirt and top, and use all your accessories to draw attention to the outfit.

How to wear a pencil skirt with unique styles

  1. Over a dress.
Blake Lively

Blake Lively

Consider wearing a dress, then putting a pencil skirt over it. This screams quirky, but since a few celebrities have done it, you could probably get away with it too.

  1. We’re in the army now.


You can try pairing a pencil skirt with army print shirts. This screams tomboy, but you add the feminine style of the pencil skirt. Olive Green or Brown pencil skirts would work best with this, and consider using Converse sneakers or Keds instead of high heels.

  1. Denim skirt.


Generally considered more formal/business wear, you can wear a pencil skirt in a variety of textures, such as denim and pair it with a denim top, and dress it down to look both playful and fun.

  1. Wild creature.
Victoria Beckham

Victoria Beckham

Choose a leopard printed skirt for a bold, daring and unique look.

  1. Flannel shirt.


Pair a jean pencil skirt with a flannel shirt, oversized sunglasses and a pair of sandals or heels. This is a relaxed, fun look, and is great for a casual lunch or outing with friends or family.

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